# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Jonathan Steed' 'Mike Bearpark' 'Christos A. Ilioudis' _publ_contact_author_name 'Dr Jonathan Steed' _publ_contact_author_address ; Department of Chemistry University of Durham University Science Laboratories South Road Durham DH1 3LE UK ; _publ_contact_author_email JON.STEED@DUR.AC.UK _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Hydrogen bonds between ammonium ions and aromatic rings exist and have key consequences on solution phase properties ; data_c:\structs\chris\tc1\tc1 _database_code_depnum_ccdc_archive 'CCDC 253845' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H42 N4 O6 S3' _chemical_formula_weight 722.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 8.6574(17) _cell_length_b 18.3472(10) _cell_length_c 22.6283(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3594.3(12) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 25147 _diffrn_reflns_av_R_equivalents 0.2725 _diffrn_reflns_av_sigmaI/netI 0.3073 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.49 _reflns_number_total 8208 _reflns_number_gt 4753 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0349P)^2^+6.1591P] 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 SHELXL _refine_ls_extinction_coef 0.0059(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(13) _refine_ls_number_reflns 8208 _refine_ls_number_parameters 446 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2120 _refine_ls_R_factor_gt 0.1203 _refine_ls_wR_factor_ref 0.1891 _refine_ls_wR_factor_gt 0.1668 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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 S1 S 0.51655(18) 0.49803(9) 0.20390(7) 0.0319(4) Uani 1 1 d . . . S2 S 1.17596(19) 0.68074(10) 0.03780(7) 0.0326(4) Uani 1 1 d . . . S3 S 0.9656(2) 0.27683(9) -0.07026(8) 0.0377(5) Uani 1 1 d . . . O1 O 1.1699(5) 0.7027(2) -0.02233(18) 0.0396(12) Uani 1 1 d . . . O2 O 0.3924(5) 0.5449(2) 0.1873(2) 0.0420(12) Uani 1 1 d . . . N2 N 0.5879(6) 0.4641(3) 0.1436(2) 0.0329(14) Uani 1 1 d . . . O4 O 0.6418(6) 0.5265(3) 0.2383(2) 0.0487(14) Uani 1 1 d . . . C19 C 0.3559(8) 0.3704(4) 0.2156(3) 0.0420(19) Uani 1 1 d . . . H19 H 0.3308 0.3764 0.1750 0.050 Uiso 1 1 calc R . . C17 C 0.3414(8) 0.2984(4) 0.3043(3) 0.0397(17) Uani 1 1 d . . . N3 N 1.0325(6) 0.6234(3) 0.0470(2) 0.0336(13) Uani 1 1 d . . . C5 C 0.5984(7) 0.4940(4) 0.0387(3) 0.0340(16) Uani 1 1 d . . . C27 C 1.1354(7) 0.7575(4) 0.0818(3) 0.0331(17) Uani 1 1 d . . . O10 O 1.0156(7) 0.2289(2) -0.0244(2) 0.0561(15) Uani 1 1 d . . . C3 C 0.7679(7) 0.4637(4) -0.0410(3) 0.0333(16) Uani 1 1 d . . . O12 O 1.3123(5) 0.6451(3) 0.0598(2) 0.0510(14) Uani 1 1 d . . . N1 N 0.9412(6) 0.4521(3) 0.0892(2) 0.0343(14) Uani 1 1 d . . . C29 C 0.9971(9) 0.8699(4) 0.0953(3) 0.0380(17) Uani 1 1 d . . . H29 H 0.9295 0.9061 0.0799 0.046 Uiso 1 1 calc R . . C35 C 1.0985(8) 0.3183(4) -0.1746(3) 0.0406(18) Uani 1 1 d . . . H35 H 0.9961 0.3214 -0.1896 0.049 Uiso 1 1 calc R . . C2 C 0.8372(8) 0.5325(4) -0.0363(3) 0.0390(17) Uani 1 1 d . . . H2 H 0.9168 0.5460 -0.0631 0.047 Uiso 1 1 calc R . . C30 C 1.1247(7) 0.2936(3) -0.1178(3) 0.0269(15) Uani 1 1 d . . . C28 C 1.0375(7) 0.8102(4) 0.0606(3) 0.0347(17) Uani 1 1 d . . . H28 H 0.9968 0.8059 0.0217 0.042 Uiso 1 1 calc R . . C32 C 1.3946(8) 0.3053(4) -0.1319(3) 0.0401(18) Uani 1 1 d . . . H32 H 1.4969 0.2994 -0.1175 0.048 Uiso 1 1 calc R . . C6 C 0.6657(7) 0.5594(4) 0.0430(3) 0.0341(16) Uani 1 1 d . . . H6 H 0.6283 0.5931 0.0715 0.041 Uiso 1 1 calc R . . C26 C 1.1939(9) 0.7630(4) 0.1386(3) 0.051(2) Uani 1 1 d . . . H26 H 1.2617 0.7268 0.1538 0.061 Uiso 1 1 calc R . . C15 C 1.0297(9) 0.5835(3) 0.1028(3) 0.0375(17) Uani 1 1 d . . . H15A H 0.9246 0.5870 0.1198 0.045 Uiso 1 1 calc R . . H15B H 1.1017 0.6074 0.1307 0.045 Uiso 1 1 calc R . . C1 C 0.7916(7) 0.5802(3) 0.0063(2) 0.0250(14) Uani 1 1 d . . . C10 C 0.7079(8) 0.4085(4) 0.1478(4) 0.0459(19) Uani 1 1 d . . . H10A H 0.6961 0.3742 0.1143 0.055 Uiso 1 1 calc R . . H10B H 0.6921 0.3805 0.1847 0.055 Uiso 1 1 calc R . . C11 C 0.8730(7) 0.4384(4) 0.1474(3) 0.0297(16) Uani 1 1 d . . . H11B H 0.8740 0.4846 0.1700 0.036 Uiso 1 1 calc R . . H11A H 0.9400 0.4035 0.1687 0.036 Uiso 1 1 calc R . . C31 C 1.2734(8) 0.2872(4) -0.0964(3) 0.0348(17) Uani 1 1 d . . . H31 H 1.2912 0.2704 -0.0573 0.042 Uiso 1 1 calc R . . C8 C 0.8461(9) 0.4067(4) -0.0798(3) 0.0464(19) Uani 1 1 d . . . H8B H 0.7684 0.3806 -0.1038 0.056 Uiso 1 1 calc R . . H8A H 0.9211 0.4303 -0.1067 0.056 Uiso 1 1 calc R . . C21 C 0.4786(9) 0.4125(4) 0.3025(3) 0.047(2) Uani 1 1 d . . . H21 H 0.5410 0.4473 0.3223 0.057 Uiso 1 1 calc R . . C4 C 0.6496(8) 0.4443(4) -0.0049(3) 0.0372(17) Uani 1 1 d . . . H4 H 0.6018 0.3980 -0.0089 0.045 Uiso 1 1 calc R . . C7 C 0.8821(7) 0.6468(4) 0.0209(3) 0.0406(18) Uani 1 1 d . . . H7A H 0.8245 0.6773 0.0495 0.049 Uiso 1 1 calc R . . H7B H 0.9004 0.6760 -0.0152 0.049 Uiso 1 1 calc R . . C12 C 1.0019(9) 0.3842(3) 0.0661(3) 0.0399(17) Uani 1 1 d . . . H12B H 0.9239 0.3456 0.0727 0.048 Uiso 1 1 calc R . . H12A H 1.0947 0.3710 0.0893 0.048 Uiso 1 1 calc R . . C20 C 0.4432(7) 0.4227(4) 0.2437(3) 0.0302(15) Uani 1 1 d . . . O33 O 0.8351(7) 0.2556(3) -0.1049(2) 0.0648(16) Uani 1 1 d . . . C23 C 1.0143(13) 0.9421(4) 0.1892(3) 0.076(3) Uani 1 1 d . . . H23B H 0.9525 0.9264 0.2232 0.114 Uiso 1 1 calc R . . H23A H 0.9549 0.9770 0.1656 0.114 Uiso 1 1 calc R . . H23C H 1.1094 0.9654 0.2032 0.114 Uiso 1 1 calc R . . C36 C 1.5077(10) 0.3541(4) -0.2277(3) 0.063(2) Uani 1 1 d . . . H36A H 1.6023 0.3559 -0.2039 0.094 Uiso 1 1 calc R . . H36B H 1.4879 0.4022 -0.2449 0.094 Uiso 1 1 calc R . . H36C H 1.5202 0.3182 -0.2594 0.094 Uiso 1 1 calc R . . C18 C 0.3044(9) 0.3098(4) 0.2452(3) 0.045(2) Uani 1 1 d . . . H18 H 0.2425 0.2750 0.2250 0.054 Uiso 1 1 calc R . . C13 C 1.0461(8) 0.3842(4) -0.0003(3) 0.0460(19) Uani 1 1 d . . . H13A H 1.0681 0.4349 -0.0126 0.055 Uiso 1 1 calc R . . H13B H 1.1422 0.3556 -0.0054 0.055 Uiso 1 1 calc R . . C14 C 1.0735(7) 0.5027(4) 0.0978(3) 0.0399(19) Uani 1 1 d . . . H14B H 1.1457 0.4968 0.0643 0.048 Uiso 1 1 calc R . . H14A H 1.1292 0.4884 0.1342 0.048 Uiso 1 1 calc R . . C16 C 0.2916(9) 0.2318(4) 0.3364(3) 0.0450(19) Uani 1 1 d . . . H16A H 0.3572 0.2248 0.3713 0.067 Uiso 1 1 calc R . . H16C H 0.3008 0.1895 0.3103 0.067 Uiso 1 1 calc R . . H16B H 0.1838 0.2373 0.3489 0.067 Uiso 1 1 calc R . . C33 C 1.3722(9) 0.3322(4) -0.1886(3) 0.0422(19) Uani 1 1 d . . . C24 C 1.0547(9) 0.8770(4) 0.1519(3) 0.048(2) Uani 1 1 d . . . C22 C 0.4263(9) 0.3536(4) 0.3325(3) 0.049(2) Uani 1 1 d . . . H22 H 0.4476 0.3496 0.3735 0.058 Uiso 1 1 calc R . . C9 C 0.4955(8) 0.4674(3) 0.0870(3) 0.0388(18) Uani 1 1 d . . . H9A H 0.4553 0.4183 0.0772 0.047 Uiso 1 1 calc R . . H9B H 0.4066 0.5008 0.0919 0.047 Uiso 1 1 calc R . . N4 N 0.9281(6) 0.3543(3) -0.0389(3) 0.0397(15) Uani 1 1 d . . . C25 C 1.1515(10) 0.8223(5) 0.1729(3) 0.055(2) Uani 1 1 d . . . H25 H 1.1899 0.8257 0.2121 0.066 Uiso 1 1 calc R . . C34 C 1.2213(9) 0.3385(4) -0.2094(3) 0.047(2) Uani 1 1 d . . . H34 H 1.2033 0.3570 -0.2480 0.057 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 S1 0.0332(9) 0.0309(9) 0.0316(9) 0.0009(8) 0.0106(8) -0.0044(8) S2 0.0260(9) 0.0408(10) 0.0310(9) 0.0099(8) 0.0030(8) -0.0046(8) S3 0.0475(11) 0.0294(10) 0.0362(10) -0.0097(8) 0.0143(9) -0.0008(8) O1 0.057(3) 0.032(3) 0.031(3) 0.010(2) 0.005(2) -0.003(2) O2 0.040(3) 0.033(3) 0.053(3) -0.001(2) 0.014(2) 0.006(2) N2 0.030(3) 0.033(3) 0.036(3) 0.007(3) 0.016(3) 0.005(2) O4 0.051(3) 0.050(3) 0.045(3) 0.003(2) 0.001(3) -0.021(2) C19 0.045(4) 0.059(5) 0.022(4) -0.001(3) 0.003(3) -0.017(4) C17 0.047(4) 0.041(4) 0.032(4) 0.002(3) 0.009(3) -0.003(4) N3 0.044(3) 0.023(3) 0.034(3) 0.004(2) 0.014(3) 0.004(3) C5 0.031(3) 0.038(4) 0.033(4) -0.005(3) 0.007(3) 0.003(3) C27 0.025(4) 0.041(4) 0.034(4) 0.017(3) -0.012(3) -0.015(3) O10 0.093(4) 0.026(3) 0.049(3) 0.011(2) 0.040(3) 0.019(3) C3 0.033(4) 0.031(4) 0.036(4) -0.008(3) -0.001(3) -0.003(3) O12 0.035(3) 0.070(4) 0.048(3) 0.005(3) 0.001(3) 0.009(3) N1 0.037(3) 0.029(3) 0.037(3) 0.002(3) 0.006(3) 0.001(3) C29 0.047(4) 0.031(4) 0.035(4) 0.000(3) 0.004(4) -0.018(4) C35 0.049(4) 0.046(5) 0.027(4) -0.012(3) 0.000(3) 0.015(4) C2 0.035(4) 0.047(4) 0.036(4) 0.014(4) 0.006(3) 0.002(3) C30 0.031(4) 0.022(3) 0.028(4) -0.004(3) 0.012(3) 0.007(3) C28 0.036(4) 0.046(4) 0.022(3) 0.002(3) -0.003(3) -0.027(3) C32 0.036(4) 0.038(4) 0.046(5) -0.007(4) -0.005(4) 0.014(3) C6 0.031(4) 0.043(4) 0.029(4) -0.011(3) -0.001(3) 0.017(3) C26 0.048(5) 0.055(5) 0.050(5) 0.014(4) -0.013(4) -0.023(4) C15 0.051(4) 0.034(4) 0.028(4) 0.000(3) 0.011(3) 0.001(4) C1 0.039(4) 0.021(3) 0.015(3) -0.008(3) -0.003(3) 0.012(3) C10 0.035(4) 0.027(4) 0.076(6) 0.011(4) 0.016(4) 0.000(3) C11 0.026(3) 0.047(4) 0.017(3) 0.001(3) 0.000(3) -0.001(3) C31 0.049(5) 0.036(4) 0.019(3) -0.002(3) 0.006(3) 0.014(3) C8 0.047(5) 0.046(5) 0.046(5) -0.005(4) 0.014(4) 0.004(4) C21 0.058(5) 0.060(5) 0.023(4) 0.002(3) 0.001(4) -0.031(4) C4 0.041(4) 0.031(4) 0.040(4) -0.002(3) 0.003(4) -0.003(3) C7 0.030(4) 0.035(4) 0.057(5) -0.007(4) 0.006(3) -0.003(3) C12 0.052(5) 0.035(4) 0.033(4) 0.006(3) 0.002(4) 0.023(3) C20 0.031(4) 0.040(4) 0.020(3) -0.003(3) 0.010(3) 0.000(3) O33 0.057(4) 0.074(4) 0.064(4) -0.028(3) 0.014(3) -0.019(3) C23 0.117(8) 0.057(6) 0.055(5) -0.022(4) -0.012(6) -0.016(6) C36 0.070(6) 0.057(5) 0.061(5) -0.007(4) 0.025(5) 0.000(5) C18 0.061(5) 0.045(5) 0.030(4) 0.006(3) -0.003(4) -0.036(4) C13 0.043(4) 0.048(5) 0.047(5) -0.011(4) 0.023(4) -0.005(4) C14 0.016(3) 0.040(4) 0.064(5) 0.029(4) -0.009(3) -0.017(3) C16 0.056(5) 0.048(5) 0.031(4) 0.003(4) 0.005(4) -0.012(4) C33 0.056(5) 0.036(4) 0.035(5) -0.004(3) 0.020(4) 0.002(4) C24 0.062(5) 0.041(5) 0.040(5) 0.000(4) 0.002(4) -0.020(4) C22 0.068(5) 0.062(5) 0.016(4) 0.005(4) 0.001(3) -0.028(4) C9 0.042(4) 0.028(4) 0.046(4) -0.006(3) 0.017(4) -0.013(3) N4 0.045(4) 0.029(3) 0.045(4) -0.011(3) 0.008(3) -0.002(3) C25 0.081(6) 0.053(5) 0.032(4) -0.004(4) -0.019(4) -0.023(5) C34 0.065(5) 0.046(5) 0.030(4) 0.003(3) 0.016(4) 0.028(4) _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 S1 O2 1.428(5) . ? S1 O4 1.433(5) . ? S1 N2 1.623(5) . ? S1 C20 1.768(6) . ? S2 O1 1.420(4) . ? S2 O12 1.439(5) . ? S2 N3 1.641(6) . ? S2 C27 1.760(7) . ? S3 O10 1.427(5) . ? S3 O33 1.429(6) . ? S3 N4 1.621(5) . ? S3 C30 1.774(6) . ? N2 C10 1.460(8) . ? N2 C9 1.510(8) . ? C19 C18 1.373(9) . ? C19 C20 1.377(9) . ? C17 C18 1.392(9) . ? C17 C22 1.404(9) . ? C17 C16 1.485(9) . ? N3 C15 1.458(7) . ? N3 C7 1.493(8) . ? C5 C6 1.338(9) . ? C5 C4 1.415(9) . ? C5 C9 1.494(9) . ? C27 C28 1.373(9) . ? C27 C26 1.386(9) . ? C3 C4 1.357(9) . ? C3 C2 1.402(9) . ? C3 C8 1.523(9) . ? N1 C12 1.450(8) . ? N1 C11 1.466(7) . ? N1 C14 1.488(8) . ? C29 C24 1.379(9) . ? C29 C28 1.394(9) . ? C35 C34 1.374(10) . ? C35 C30 1.384(9) . ? C2 C1 1.359(9) . ? C30 C31 1.380(9) . ? C32 C31 1.362(9) . ? C32 C33 1.386(9) . ? C6 C1 1.423(9) . ? C26 C25 1.386(11) . ? C15 C14 1.534(9) . ? C1 C7 1.490(9) . ? C10 C11 1.531(9) . ? C8 N4 1.511(9) . ? C21 C22 1.353(9) . ? C21 C20 1.377(8) . ? C12 C13 1.551(9) . ? C23 C24 1.505(10) . ? C36 C33 1.524(10) . ? C13 N4 1.452(9) . ? C33 C34 1.394(10) . ? C24 C25 1.391(11) . ? 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 O2 S1 O4 119.6(3) . . ? O2 S1 N2 107.2(3) . . ? O4 S1 N2 108.0(3) . . ? O2 S1 C20 109.6(3) . . ? O4 S1 C20 106.2(3) . . ? N2 S1 C20 105.4(3) . . ? O1 S2 O12 119.4(3) . . ? O1 S2 N3 106.0(3) . . ? O12 S2 N3 106.5(3) . . ? O1 S2 C27 108.0(3) . . ? O12 S2 C27 109.4(3) . . ? N3 S2 C27 106.9(3) . . ? O10 S3 O33 118.1(4) . . ? O10 S3 N4 106.4(3) . . ? O33 S3 N4 108.7(3) . . ? O10 S3 C30 108.2(3) . . ? O33 S3 C30 109.2(3) . . ? N4 S3 C30 105.6(3) . . ? C10 N2 C9 117.4(6) . . ? C10 N2 S1 118.9(5) . . ? C9 N2 S1 119.7(4) . . ? C18 C19 C20 121.1(6) . . ? C18 C17 C22 116.6(6) . . ? C18 C17 C16 121.8(6) . . ? C22 C17 C16 121.6(6) . . ? C15 N3 C7 118.2(5) . . ? C15 N3 S2 116.4(5) . . ? C7 N3 S2 115.1(4) . . ? C6 C5 C4 119.6(6) . . ? C6 C5 C9 120.0(6) . . ? C4 C5 C9 119.1(6) . . ? C28 C27 C26 119.9(7) . . ? C28 C27 S2 119.3(5) . . ? C26 C27 S2 120.7(6) . . ? C4 C3 C2 120.9(6) . . ? C4 C3 C8 120.1(6) . . ? C2 C3 C8 118.1(6) . . ? C12 N1 C11 108.8(5) . . ? C12 N1 C14 107.7(5) . . ? C11 N1 C14 107.4(5) . . ? C24 C29 C28 120.4(7) . . ? C34 C35 C30 119.6(7) . . ? C1 C2 C3 120.6(6) . . ? C31 C30 C35 120.4(6) . . ? C31 C30 S3 119.8(5) . . ? C35 C30 S3 119.6(5) . . ? C27 C28 C29 120.8(6) . . ? C31 C32 C33 121.6(7) . . ? C5 C6 C1 122.0(6) . . ? C27 C26 C25 118.7(7) . . ? N3 C15 C14 114.7(5) . . ? C2 C1 C6 117.7(6) . . ? C2 C1 C7 122.2(6) . . ? C6 C1 C7 119.5(5) . . ? N2 C10 C11 114.4(5) . . ? N1 C11 C10 116.3(5) . . ? C32 C31 C30 119.4(6) . . ? N4 C8 C3 107.1(5) . . ? C22 C21 C20 121.2(6) . . ? C3 C4 C5 119.1(6) . . ? C1 C7 N3 108.1(5) . . ? N1 C12 C13 116.0(5) . . ? C19 C20 C21 118.2(6) . . ? C19 C20 S1 120.4(5) . . ? C21 C20 S1 121.2(5) . . ? C19 C18 C17 121.0(6) . . ? N4 C13 C12 114.2(6) . . ? N1 C14 C15 115.0(5) . . ? C32 C33 C34 118.3(7) . . ? C32 C33 C36 121.6(7) . . ? C34 C33 C36 120.2(7) . . ? C29 C24 C25 117.9(7) . . ? C29 C24 C23 120.8(7) . . ? C25 C24 C23 121.4(7) . . ? C21 C22 C17 121.6(6) . . ? C5 C9 N2 108.5(5) . . ? C13 N4 C8 117.3(6) . . ? C13 N4 S3 117.0(5) . . ? C8 N4 S3 112.7(5) . . ? C26 C25 C24 122.3(7) . . ? C35 C34 C33 120.6(7) . . ? 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 O2 S1 N2 C10 -174.2(5) . . . . ? O4 S1 N2 C10 55.7(5) . . . . ? C20 S1 N2 C10 -57.5(5) . . . . ? O2 S1 N2 C9 -17.1(5) . . . . ? O4 S1 N2 C9 -147.1(4) . . . . ? C20 S1 N2 C9 99.7(5) . . . . ? O1 S2 N3 C15 169.9(4) . . . . ? O12 S2 N3 C15 41.7(5) . . . . ? C27 S2 N3 C15 -75.1(5) . . . . ? O1 S2 N3 C7 -45.5(5) . . . . ? O12 S2 N3 C7 -173.7(5) . . . . ? C27 S2 N3 C7 69.5(5) . . . . ? O1 S2 C27 C28 31.4(6) . . . . ? O12 S2 C27 C28 162.8(5) . . . . ? N3 S2 C27 C28 -82.3(5) . . . . ? O1 S2 C27 C26 -152.4(5) . . . . ? O12 S2 C27 C26 -21.0(6) . . . . ? N3 S2 C27 C26 94.0(6) . . . . ? C4 C3 C2 C1 2.8(10) . . . . ? C8 C3 C2 C1 -166.6(6) . . . . ? C34 C35 C30 C31 -1.7(10) . . . . ? C34 C35 C30 S3 173.2(5) . . . . ? O10 S3 C30 C31 -25.4(6) . . . . ? O33 S3 C30 C31 -155.1(5) . . . . ? N4 S3 C30 C31 88.2(6) . . . . ? O10 S3 C30 C35 159.6(5) . . . . ? O33 S3 C30 C35 29.9(6) . . . . ? N4 S3 C30 C35 -86.8(6) . . . . ? C26 C27 C28 C29 0.7(9) . . . . ? S2 C27 C28 C29 177.0(5) . . . . ? C24 C29 C28 C27 -0.2(10) . . . . ? C4 C5 C6 C1 -2.1(10) . . . . ? C9 C5 C6 C1 164.6(6) . . . . ? C28 C27 C26 C25 0.0(10) . . . . ? S2 C27 C26 C25 -176.3(5) . . . . ? C7 N3 C15 C14 109.6(7) . . . . ? S2 N3 C15 C14 -107.0(6) . . . . ? C3 C2 C1 C6 -3.8(9) . . . . ? C3 C2 C1 C7 167.1(6) . . . . ? C5 C6 C1 C2 3.5(9) . . . . ? C5 C6 C1 C7 -167.7(6) . . . . ? C9 N2 C10 C11 110.7(7) . . . . ? S1 N2 C10 C11 -91.6(6) . . . . ? C12 N1 C11 C10 -82.5(7) . . . . ? C14 N1 C11 C10 161.1(6) . . . . ? N2 C10 C11 N1 -84.7(8) . . . . ? C33 C32 C31 C30 2.0(10) . . . . ? C35 C30 C31 C32 -0.2(10) . . . . ? S3 C30 C31 C32 -175.2(5) . . . . ? C4 C3 C8 N4 -66.6(8) . . . . ? C2 C3 C8 N4 102.8(7) . . . . ? C2 C3 C4 C5 -1.2(10) . . . . ? C8 C3 C4 C5 167.9(6) . . . . ? C6 C5 C4 C3 0.9(10) . . . . ? C9 C5 C4 C3 -165.8(6) . . . . ? C2 C1 C7 N3 -66.3(8) . . . . ? C6 C1 C7 N3 104.5(6) . . . . ? C15 N3 C7 C1 -63.5(7) . . . . ? S2 N3 C7 C1 152.6(4) . . . . ? C11 N1 C12 C13 167.1(6) . . . . ? C14 N1 C12 C13 -76.7(7) . . . . ? C18 C19 C20 C21 0.3(10) . . . . ? C18 C19 C20 S1 176.8(6) . . . . ? C22 C21 C20 C19 -1.6(11) . . . . ? C22 C21 C20 S1 -178.0(6) . . . . ? O2 S1 C20 C19 69.4(6) . . . . ? O4 S1 C20 C19 -160.1(5) . . . . ? N2 S1 C20 C19 -45.7(6) . . . . ? O2 S1 C20 C21 -114.2(6) . . . . ? O4 S1 C20 C21 16.3(7) . . . . ? N2 S1 C20 C21 130.7(6) . . . . ? C20 C19 C18 C17 -1.3(12) . . . . ? C22 C17 C18 C19 3.3(11) . . . . ? C16 C17 C18 C19 -177.7(7) . . . . ? N1 C12 C13 N4 -97.5(8) . . . . ? C12 N1 C14 C15 161.3(5) . . . . ? C11 N1 C14 C15 -81.7(7) . . . . ? N3 C15 C14 N1 -92.5(7) . . . . ? C31 C32 C33 C34 -1.7(11) . . . . ? C31 C32 C33 C36 178.6(6) . . . . ? C28 C29 C24 C25 -0.9(10) . . . . ? C28 C29 C24 C23 178.7(7) . . . . ? C20 C21 C22 C17 3.7(12) . . . . ? C18 C17 C22 C21 -4.5(12) . . . . ? C16 C17 C22 C21 176.5(7) . . . . ? C6 C5 C9 N2 -59.5(8) . . . . ? C4 C5 C9 N2 107.2(6) . . . . ? C10 N2 C9 C5 -69.6(7) . . . . ? S1 N2 C9 C5 132.9(5) . . . . ? C12 C13 N4 C8 110.8(6) . . . . ? C12 C13 N4 S3 -110.7(6) . . . . ? C3 C8 N4 C13 -59.8(7) . . . . ? C3 C8 N4 S3 160.0(4) . . . . ? O10 S3 N4 C13 50.2(6) . . . . ? O33 S3 N4 C13 178.4(5) . . . . ? C30 S3 N4 C13 -64.6(5) . . . . ? O10 S3 N4 C8 -169.5(5) . . . . ? O33 S3 N4 C8 -41.3(5) . . . . ? C30 S3 N4 C8 75.7(5) . . . . ? C27 C26 C25 C24 -1.2(11) . . . . ? C29 C24 C25 C26 1.6(11) . . . . ? C23 C24 C25 C26 -178.0(7) . . . . ? C30 C35 C34 C33 2.0(10) . . . . ? C32 C33 C34 C35 -0.3(10) . . . . ? C36 C33 C34 C35 179.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.604 _refine_diff_density_min -0.726 _refine_diff_density_rms 0.182 data_c:\structs\chris\c1cl\c1cl _database_code_depnum_ccdc_archive 'CCDC 253846' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H31 Cl4 N4 O2' _chemical_formula_weight 441.24 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' Cl Cl 0.1484 0.1585 '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' _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 9.4427(19) _cell_length_b 9.947(2) _cell_length_c 12.252(3) _cell_angle_alpha 84.27(3) _cell_angle_beta 73.42(3) _cell_angle_gamma 74.08(3) _cell_volume 1060.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 466 _exptl_absorpt_coefficient_mu 0.575 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3625 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.1169 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2660 _reflns_number_gt 1709 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0190P)^2^+0.4557P] 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 SHELXL _refine_ls_extinction_coef 0.0031(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2660 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1053 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.545 _refine_ls_shift/su_mean 0.002 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 0.16615(15) 0.13066(13) 0.03675(10) 0.0278(4) Uani 1 1 d . . . Cl3 Cl -0.10299(15) 0.57614(14) -0.28138(10) 0.0291(4) Uani 1 1 d . . . Cl4 Cl -0.65843(15) 0.79284(14) -0.21043(11) 0.0335(4) Uani 1 1 d . . . N1 N -0.4500(5) -0.0104(4) -0.2958(3) 0.0238(11) Uani 1 1 d . . . H11 H -0.4922 0.0621 -0.3391 0.029 Uiso 1 1 calc R . . H12 H -0.5056 -0.0757 -0.2854 0.029 Uiso 1 1 calc R . . N3 N -0.3033(6) 0.5002(5) -0.4146(4) 0.0253(12) Uani 1 1 d . . . N4 N -0.3718(5) 0.2662(5) -0.1888(4) 0.0201(11) Uani 1 1 d . . . C1 C -0.1596(6) 0.2552(5) -0.4530(4) 0.0201(13) Uani 1 1 d . . . N2 N -0.0280(5) 0.1282(5) -0.1227(3) 0.0240(12) Uani 1 1 d . . . C12 C -0.3156(6) 0.2377(5) -0.0825(4) 0.0242(13) Uani 1 1 d . . . H12A H -0.3142 0.1399 -0.0567 0.029 Uiso 1 1 calc R . . H12B H -0.3906 0.2992 -0.0219 0.029 Uiso 1 1 calc R . . C7 C -0.2878(6) -0.0769(5) -0.3638(4) 0.0257(13) Uani 1 1 d . . . H7A H -0.2424 -0.1601 -0.3217 0.031 Uiso 1 1 calc R . . H7B H -0.2889 -0.1076 -0.4379 0.031 Uiso 1 1 calc R . . C4 C -0.0866(6) 0.0139(5) -0.3228(4) 0.0221(13) Uani 1 1 d . . . H4 H -0.0603 -0.0692 -0.2793 0.027 Uiso 1 1 calc R . . C11 C -0.5060(6) 0.2033(5) -0.1753(4) 0.0248(13) Uani 1 1 d . . . H11A H -0.5803 0.2320 -0.1010 0.030 Uiso 1 1 calc R . . H11B H -0.5573 0.2450 -0.2354 0.030 Uiso 1 1 calc R . . C8 C 0.0735(6) 0.1190(5) -0.2425(4) 0.0261(14) Uani 1 1 d . . . H8A H 0.1214 0.1984 -0.2593 0.031 Uiso 1 1 calc R . . H8B H 0.1560 0.0312 -0.2506 0.031 Uiso 1 1 calc R . . C6 C -0.2267(6) 0.1466(5) -0.4500(4) 0.0218(13) Uani 1 1 d . . . H6 H -0.2965 0.1542 -0.4942 0.026 Uiso 1 1 calc R . . C10 C -0.4699(6) 0.0451(5) -0.1812(4) 0.0228(13) Uani 1 1 d . . . H10A H -0.3748 0.0036 -0.1575 0.027 Uiso 1 1 calc R . . H10B H -0.5533 0.0128 -0.1253 0.027 Uiso 1 1 calc R . . C3 C -0.0172(5) 0.1223(5) -0.3250(4) 0.0208(13) Uani 1 1 d . . . C13 C -0.1575(6) 0.2588(5) -0.0941(4) 0.0248(13) Uani 1 1 d . . . H13A H -0.1381 0.3308 -0.1543 0.030 Uiso 1 1 calc R . . H13B H -0.1578 0.2950 -0.0216 0.030 Uiso 1 1 calc R . . C9 C -0.2174(6) 0.3942(5) -0.5063(4) 0.0250(13) Uani 1 1 d . . . H9A H -0.2860 0.3857 -0.5516 0.030 Uiso 1 1 calc R . . H9B H -0.1303 0.4256 -0.5581 0.030 Uiso 1 1 calc R . . C5 C -0.1932(5) 0.0269(5) -0.3834(4) 0.0197(13) Uani 1 1 d . . . C15 C -0.4418(5) 0.4696(5) -0.3296(4) 0.0211(13) Uani 1 1 d . . . H15A H -0.4713 0.3958 -0.3599 0.025 Uiso 1 1 calc R . . H15B H -0.5277 0.5548 -0.3212 0.025 Uiso 1 1 calc R . . C2 C -0.0524(6) 0.2404(5) -0.3919(4) 0.0229(13) Uani 1 1 d . . . H2 H -0.0025 0.3125 -0.3963 0.027 Uiso 1 1 calc R . . C14 C -0.4181(6) 0.4223(5) -0.2124(4) 0.0229(13) Uani 1 1 d . . . H14A H -0.3387 0.4631 -0.2014 0.028 Uiso 1 1 calc R . . H14B H -0.5143 0.4626 -0.1545 0.028 Uiso 1 1 calc R . . Cl2 Cl 0.37995(15) 0.23789(13) 0.56650(10) 0.0279(4) Uani 1 1 d . . . O1 O -0.2961(5) 0.5656(4) -0.0184(3) 0.0396(11) Uani 1 1 d . . . O2 O -0.8097(5) 0.5360(4) -0.1762(3) 0.0454(12) Uani 1 1 d . . . H41 H -0.303(5) 0.230(4) -0.245(3) 0.000(13) Uiso 1 1 d . . . H31 H -0.235(7) 0.529(6) -0.375(4) 0.064(19) Uiso 1 1 d . . . H21 H 0.042(6) 0.131(5) -0.064(4) 0.048(16) Uiso 1 1 d . . . H32 H -0.336(6) 0.573(5) -0.443(4) 0.029(19) Uiso 1 1 d . . . H22 H -0.067(5) 0.051(5) -0.099(4) 0.031(15) Uiso 1 1 d . . . H201 H -0.770(13) 0.633(11) -0.190(9) 0.22(5) Uiso 1 1 d . . . H202 H -0.883(8) 0.526(7) -0.207(6) 0.10(3) Uiso 1 1 d . . . H102 H -0.236(8) 0.549(7) 0.021(6) 0.09(3) 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 0.0331(9) 0.0254(9) 0.0311(8) 0.0039(6) -0.0150(7) -0.0128(7) Cl3 0.0299(9) 0.0286(9) 0.0327(8) 0.0013(7) -0.0093(7) -0.0135(7) Cl4 0.0335(9) 0.0244(9) 0.0436(8) 0.0001(7) -0.0065(7) -0.0134(7) N1 0.032(3) 0.017(3) 0.030(2) 0.003(2) -0.014(2) -0.015(2) N3 0.027(3) 0.017(3) 0.030(3) 0.006(3) -0.006(2) -0.006(3) N4 0.020(3) 0.027(3) 0.015(2) -0.003(2) 0.000(2) -0.012(2) C1 0.024(3) 0.019(3) 0.015(3) 0.004(2) -0.005(2) -0.003(3) N2 0.025(3) 0.024(3) 0.030(3) 0.006(2) -0.012(2) -0.014(3) C12 0.033(4) 0.023(3) 0.018(3) -0.007(2) -0.006(3) -0.007(3) C7 0.026(4) 0.018(3) 0.032(3) -0.003(3) -0.010(3) -0.001(3) C4 0.024(3) 0.017(3) 0.019(3) -0.001(2) 0.000(3) 0.000(3) C11 0.023(3) 0.030(4) 0.024(3) 0.005(3) -0.003(2) -0.016(3) C8 0.024(3) 0.026(4) 0.028(3) 0.004(3) -0.004(3) -0.011(3) C6 0.025(3) 0.021(4) 0.018(3) -0.002(3) -0.007(2) -0.003(3) C10 0.030(3) 0.012(3) 0.030(3) 0.004(3) -0.008(3) -0.014(3) C3 0.020(3) 0.020(3) 0.023(3) 0.002(3) -0.004(3) -0.009(3) C13 0.025(3) 0.024(4) 0.025(3) -0.002(3) -0.005(3) -0.007(3) C9 0.022(3) 0.029(4) 0.021(3) 0.004(3) -0.002(3) -0.007(3) C5 0.018(3) 0.022(3) 0.018(3) -0.006(3) -0.001(2) -0.006(3) C15 0.017(3) 0.023(3) 0.023(3) 0.003(2) -0.001(2) -0.010(3) C2 0.026(3) 0.022(3) 0.019(3) -0.005(3) 0.004(3) -0.012(3) C14 0.028(3) 0.016(3) 0.024(3) -0.001(2) -0.001(2) -0.009(3) Cl2 0.0358(9) 0.0230(9) 0.0310(8) 0.0051(6) -0.0161(7) -0.0119(7) O1 0.035(3) 0.043(3) 0.042(3) -0.006(2) -0.006(2) -0.015(2) O2 0.044(3) 0.044(3) 0.057(3) 0.008(2) -0.021(2) -0.020(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 N1 C10 1.503(5) . ? N1 C7 1.517(6) . ? N3 C15 1.505(6) . ? N3 C9 1.510(6) . ? N4 C12 1.515(6) . ? N4 C14 1.516(6) . ? N4 C11 1.524(6) . ? C1 C6 1.386(6) . ? C1 C2 1.392(6) . ? C1 C9 1.498(6) . ? N2 C8 1.503(6) . ? N2 C13 1.510(6) . ? C12 C13 1.529(6) . ? C7 C5 1.502(6) . ? C4 C5 1.384(6) . ? C4 C3 1.401(6) . ? C11 C10 1.520(6) . ? C8 C3 1.493(6) . ? C6 C5 1.390(6) . ? C3 C2 1.383(6) . ? C15 C14 1.524(6) . ? 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 C10 N1 C7 117.0(4) . . ? C15 N3 C9 116.5(4) . . ? C12 N4 C14 110.0(4) . . ? C12 N4 C11 110.4(3) . . ? C14 N4 C11 110.4(4) . . ? C6 C1 C2 119.0(4) . . ? C6 C1 C9 120.8(4) . . ? C2 C1 C9 119.6(4) . . ? C8 N2 C13 116.7(4) . . ? N4 C12 C13 116.3(4) . . ? C5 C7 N1 109.7(4) . . ? C5 C4 C3 120.5(4) . . ? C10 C11 N4 117.0(4) . . ? C3 C8 N2 110.3(4) . . ? C1 C6 C5 121.0(5) . . ? N1 C10 C11 115.5(4) . . ? C2 C3 C4 119.1(4) . . ? C2 C3 C8 120.5(4) . . ? C4 C3 C8 119.7(4) . . ? N2 C13 C12 114.4(4) . . ? C1 C9 N3 109.8(4) . . ? C4 C5 C6 119.3(4) . . ? C4 C5 C7 120.0(4) . . ? C6 C5 C7 120.1(4) . . ? N3 C15 C14 114.0(4) . . ? C3 C2 C1 121.0(4) . . ? N4 C14 C15 117.1(4) . . ? 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 C14 N4 C12 C13 -73.8(5) . . . . ? C11 N4 C12 C13 164.1(4) . . . . ? C10 N1 C7 C5 -58.3(5) . . . . ? C12 N4 C11 C10 -73.2(5) . . . . ? C14 N4 C11 C10 164.9(4) . . . . ? C13 N2 C8 C3 -61.3(5) . . . . ? C2 C1 C6 C5 2.8(7) . . . . ? C9 C1 C6 C5 -168.2(4) . . . . ? C7 N1 C10 C11 104.7(5) . . . . ? N4 C11 C10 N1 -95.7(5) . . . . ? C5 C4 C3 C2 -2.4(7) . . . . ? C5 C4 C3 C8 168.1(4) . . . . ? N2 C8 C3 C2 106.6(5) . . . . ? N2 C8 C3 C4 -63.8(6) . . . . ? C8 N2 C13 C12 106.1(5) . . . . ? N4 C12 C13 N2 -93.1(5) . . . . ? C6 C1 C9 N3 106.9(5) . . . . ? C2 C1 C9 N3 -64.0(6) . . . . ? C15 N3 C9 C1 -60.6(6) . . . . ? C3 C4 C5 C6 2.4(7) . . . . ? C3 C4 C5 C7 -168.7(4) . . . . ? C1 C6 C5 C4 -2.6(7) . . . . ? C1 C6 C5 C7 168.5(4) . . . . ? N1 C7 C5 C4 105.7(5) . . . . ? N1 C7 C5 C6 -65.3(5) . . . . ? C9 N3 C15 C14 106.2(5) . . . . ? C4 C3 C2 C1 2.6(7) . . . . ? C8 C3 C2 C1 -167.9(4) . . . . ? C6 C1 C2 C3 -2.8(7) . . . . ? C9 C1 C2 C3 168.2(4) . . . . ? C12 N4 C14 C15 166.1(4) . . . . ? C11 N4 C14 C15 -71.9(5) . . . . ? N3 C15 C14 N4 -94.7(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 N1 H11 Cl2 0.92 2.26 3.172(4) 173.9 1_454 N1 H12 Cl4 0.92 2.16 3.054(4) 163.1 1_545 N2 H21 Cl1 1.11(5) 1.93(5) 3.041(4) 178(4) . N3 H32 Cl2 0.79(5) 2.32(5) 3.089(6) 165(5) 2_565 N2 H22 Cl1 0.93(5) 2.23(5) 3.156(5) 178(4) 2 O2 H201 Cl4 1.11(11) 2.09(12) 3.192(5) 170(8) . O2 H202 Cl3 0.91(7) 2.41(7) 3.289(5) 162(6) 1_455 O1 H102 O2 0.82(6) 2.11(7) 2.833(6) 147(7) 2_465 _diffrn_measured_fraction_theta_max 0.546 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.546 _refine_diff_density_max 0.368 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.082