# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Steve Archibald' 'Ross W. Boyle' 'Eleanor Rogerson' 'Amanda E. Sparke' 'Jonathon M. Sutton' 'Christopher J. Wilson' _publ_contact_author_name 'Dr Steve Archibald' _publ_contact_author_address ; Department of Chemistry The University of Hull Kingston upon Hull Hull UNITED KINGDOM ; _publ_contact_author_email S.J.ARCHIBALD@HULL.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Synthesis and structural characterisation of novel bimetallic dipyrromethene complexes: rotational locking of the 5-aryl group ; data_ps1_03 _database_code_depnum_ccdc_archive 'CCDC 234540' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H62 Cl2 N6 O Zn2' _chemical_formula_weight 940.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' H H 0.0000 0.0000 '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 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 11.4184(12) _cell_length_b 24.785(4) _cell_length_c 16.7968(17) _cell_angle_alpha 90.00 _cell_angle_beta 106.345(8) _cell_angle_gamma 90.00 _cell_volume 4561.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1976 _exptl_absorpt_coefficient_mu 1.212 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Stoe IPDSII image plate' _diffrn_measurement_method '78 frames at 2^o intervals, exposure time 2 minutes' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 56160 _diffrn_reflns_av_R_equivalents 0.1044 _diffrn_reflns_av_sigmaI/netI 0.2372 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 35.11 _reflns_number_total 19879 _reflns_number_gt 6757 _reflns_threshold_expression >2sigma(I) _computing_data_collection X-AREA _computing_cell_refinement X-AREA _computing_data_reduction X-RED _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP II (Johnson, 1976)' _computing_publication_material 'SHELXL 97 (Sheldrick, 1997)' _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^)+(0.0496P)^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 0.00175(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 19879 _refine_ls_number_parameters 533 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1762 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 0.697 _refine_ls_restrained_S_all 0.697 _refine_ls_shift/su_max 0.024 _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 Zn2 Zn 0.16759(3) 0.861718(15) 0.41830(2) 0.02173(8) Uani 1 1 d . . . Zn1 Zn 0.24958(3) 0.807921(14) 0.13443(2) 0.02035(8) Uani 1 1 d . . . Cl1 Cl 0.25193(7) 0.78842(3) 0.00418(5) 0.02949(17) Uani 1 1 d . . . Cl2 Cl 0.12490(9) 0.86933(4) 0.54054(5) 0.0401(2) Uani 1 1 d . . . N4 N 0.0828(2) 0.93027(10) 0.35284(15) 0.0215(5) Uani 1 1 d . . . C15 C 0.0484(3) 0.85761(12) 0.19050(16) 0.0192(5) Uani 1 1 d . . . N6 N 0.3415(2) 0.85954(10) 0.42341(14) 0.0213(5) Uani 1 1 d . . . C17 C -0.1154(3) 0.80264(13) 0.14208(18) 0.0235(6) Uani 1 1 d . . . N3 N 0.0843(2) 0.81442(10) 0.14855(14) 0.0205(5) Uani 1 1 d . . . N5 N 0.1255(2) 0.79207(10) 0.36108(15) 0.0215(5) Uani 1 1 d . . . C10 C 0.3144(3) 0.96056(13) 0.24550(19) 0.0237(6) Uani 1 1 d . . . C6 C 0.1256(3) 0.89993(12) 0.22587(17) 0.0187(5) Uani 1 1 d . . . C28 C 0.3232(3) 0.78106(12) 0.33112(17) 0.0199(6) Uani 1 1 d . . . N2 N 0.3020(2) 0.88129(10) 0.17318(15) 0.0209(5) Uani 1 1 d . . . C24 C 0.4804(3) 0.71037(13) 0.33467(19) 0.0254(6) Uani 1 1 d . . . H24 H 0.4921 0.7070 0.3915 0.031 Uiso 1 1 calc R . . C22 C -0.1644(3) 0.88381(13) 0.2178(2) 0.0271(7) Uani 1 1 d . . . H22A H -0.1208 0.9144 0.2465 0.041 Uiso 1 1 calc R . . H22B H -0.1966 0.8631 0.2551 0.041 Uiso 1 1 calc R . . H22C H -0.2302 0.8959 0.1720 0.041 Uiso 1 1 calc R . . C23 C 0.3945(3) 0.74590(12) 0.28901(17) 0.0206(6) Uani 1 1 d . . . C9 C 0.4116(3) 0.95830(14) 0.2108(2) 0.0272(7) Uani 1 1 d . . . C27 C 0.4398(3) 0.72120(13) 0.16829(19) 0.0256(6) Uani 1 1 d . . . H27 H 0.4254 0.7243 0.1112 0.031 Uiso 1 1 calc R . . C5 C 0.0340(3) 0.96698(13) 0.3947(2) 0.0283(7) Uani 1 1 d . . . H5 H 0.0399 0.9605 0.4502 0.034 Uiso 1 1 calc R . . C40 C 0.5113(3) 0.84297(12) 0.38034(18) 0.0225(6) Uani 1 1 d . . . C2 C 0.0142(3) 0.98594(13) 0.2326(2) 0.0263(6) Uani 1 1 d . . . H2 H 0.0077 0.9916 0.1768 0.032 Uiso 1 1 calc R . . C31 C 0.0315(3) 0.71392(13) 0.30803(19) 0.0260(6) Uani 1 1 d . . . C29 C 0.2062(3) 0.76221(12) 0.32866(18) 0.0210(6) Uani 1 1 d . . . C32 C 0.1458(3) 0.71250(13) 0.29574(19) 0.0248(6) Uani 1 1 d . . . C4 C -0.0238(3) 1.01342(14) 0.3586(2) 0.0324(7) Uani 1 1 d . . . H4 H -0.0550 1.0378 0.3894 0.039 Uiso 1 1 calc R . . C16 C -0.0117(3) 0.78217(13) 0.12060(18) 0.0240(6) Uani 1 1 d . . . C12 C 0.5065(3) 1.00106(15) 0.2141(2) 0.0353(8) Uani 1 1 d . . . H12A H 0.4723 1.0359 0.2215 0.042 Uiso 1 1 calc R . . H12B H 0.5252 1.0017 0.1613 0.042 Uiso 1 1 calc R . . C30 C 0.0233(3) 0.76363(13) 0.34790(19) 0.0248(6) Uani 1 1 d . . . C44 C 0.6021(3) 0.82318(14) 0.3377(2) 0.0302(7) Uani 1 1 d . . . H44A H 0.5661 0.7949 0.2996 0.045 Uiso 1 1 calc R . . H44B H 0.6729 0.8096 0.3783 0.045 Uiso 1 1 calc R . . H44C H 0.6255 0.8524 0.3079 0.045 Uiso 1 1 calc R . . C26 C 0.5281(3) 0.68574(14) 0.2104(2) 0.0295(7) Uani 1 1 d . . . H26 H 0.5731 0.6660 0.1822 0.035 Uiso 1 1 calc R . . C7 C 0.2433(3) 0.91291(12) 0.21904(18) 0.0203(6) Uani 1 1 d . . . C39 C 0.5378(3) 0.88411(13) 0.43881(19) 0.0255(6) Uani 1 1 d . . . N1 N 0.3728(2) 0.75173(10) 0.20585(15) 0.0207(5) Uani 1 1 d . . . C25 C 0.5495(3) 0.67971(14) 0.2952(2) 0.0313(7) Uani 1 1 d . . . H25 H 0.6085 0.6558 0.3250 0.038 Uiso 1 1 calc R . . C18 C -0.0791(3) 0.84924(12) 0.18603(17) 0.0214(6) Uani 1 1 d . . . C41 C 0.4133(4) 0.93229(15) 0.5269(2) 0.0366(8) Uani 1 1 d . . . H41A H 0.3311 0.9296 0.5306 0.055 Uiso 1 1 calc R . . H41B H 0.4280 0.9683 0.5109 0.055 Uiso 1 1 calc R . . H41C H 0.4693 0.9240 0.5799 0.055 Uiso 1 1 calc R . . C34 C -0.0685(3) 0.67228(15) 0.2854(2) 0.0373(8) Uani 1 1 d . . . H34A H -0.0562 0.6498 0.2412 0.045 Uiso 1 1 calc R . . H34B H -0.1463 0.6905 0.2644 0.045 Uiso 1 1 calc R . . C37 C 0.3871(3) 0.82641(12) 0.37244(17) 0.0206(6) Uani 1 1 d . . . C14 C 0.2981(3) 1.00636(14) 0.3006(2) 0.0331(7) Uani 1 1 d . . . H14A H 0.2257 1.0004 0.3177 0.050 Uiso 1 1 calc R . . H14B H 0.2906 1.0397 0.2706 0.050 Uiso 1 1 calc R . . H14C H 0.3676 1.0081 0.3486 0.050 Uiso 1 1 calc R . . C20 C -0.2393(3) 0.77692(14) 0.1175(2) 0.0311(7) Uani 1 1 d . . . H20A H -0.2780 0.7825 0.1614 0.037 Uiso 1 1 calc R . . H20B H -0.2302 0.7384 0.1114 0.037 Uiso 1 1 calc R . . C8 C 0.4014(3) 0.90850(13) 0.16878(19) 0.0253(6) Uani 1 1 d . . . C33 C -0.0844(3) 0.78355(15) 0.3730(2) 0.0345(8) Uani 1 1 d . . . H33A H -0.0662 0.8183 0.3988 0.052 Uiso 1 1 calc R . . H33B H -0.1031 0.7586 0.4114 0.052 Uiso 1 1 calc R . . H33C H -0.1534 0.7866 0.3248 0.052 Uiso 1 1 calc R . . C36 C 0.1926(3) 0.66573(15) 0.2569(2) 0.0365(8) Uani 1 1 d . . . H36A H 0.2740 0.6734 0.2545 0.055 Uiso 1 1 calc R . . H36B H 0.1404 0.6600 0.2018 0.055 Uiso 1 1 calc R . . H36C H 0.1934 0.6339 0.2896 0.055 Uiso 1 1 calc R . . C1 C 0.0722(3) 0.94054(12) 0.27220(18) 0.0205(6) Uani 1 1 d . . . C3 C -0.0344(3) 1.02305(13) 0.2761(2) 0.0313(7) Uani 1 1 d . . . H3 H -0.0734 1.0539 0.2501 0.038 Uiso 1 1 calc R . . C43 C 0.7462(4) 0.87911(17) 0.5417(3) 0.0470(10) Uani 1 1 d . . . H43A H 0.8216 0.8985 0.5615 0.071 Uiso 1 1 calc R . . H43B H 0.7616 0.8448 0.5201 0.071 Uiso 1 1 calc R . . H43C H 0.7108 0.8736 0.5866 0.071 Uiso 1 1 calc R . . C42 C 0.6594(3) 0.91107(14) 0.4741(2) 0.0331(7) Uani 1 1 d . . . H42A H 0.6463 0.9460 0.4961 0.040 Uiso 1 1 calc R . . H42B H 0.6968 0.9171 0.4297 0.040 Uiso 1 1 calc R . . C11 C 0.4842(3) 0.88667(15) 0.1215(2) 0.0312(7) Uani 1 1 d . . . H11A H 0.4553 0.8519 0.0992 0.047 Uiso 1 1 calc R . . H11B H 0.5653 0.8833 0.1580 0.047 Uiso 1 1 calc R . . H11C H 0.4849 0.9108 0.0770 0.047 Uiso 1 1 calc R . . C19 C -0.0077(3) 0.73135(14) 0.0736(2) 0.0317(7) Uani 1 1 d . . . H19A H 0.0725 0.7267 0.0670 0.048 Uiso 1 1 calc R . . H19B H -0.0662 0.7335 0.0200 0.048 Uiso 1 1 calc R . . H19C H -0.0268 0.7012 0.1036 0.048 Uiso 1 1 calc R . . C38 C 0.4311(3) 0.89297(12) 0.46314(19) 0.0249(6) Uani 1 1 d . . . C13 C 0.6238(3) 0.99316(17) 0.2825(3) 0.0431(9) Uani 1 1 d . . . H13A H 0.6795 1.0218 0.2806 0.065 Uiso 1 1 calc R . . H13B H 0.6597 0.9592 0.2750 0.065 Uiso 1 1 calc R . . H13C H 0.6067 0.9935 0.3352 0.065 Uiso 1 1 calc R . . O1 O -0.0969(3) 1.04717(13) 0.05625(18) 0.0557(8) Uani 1 1 d . . . C21 C -0.3218(3) 0.79969(18) 0.0364(2) 0.0419(9) Uani 1 1 d . . . H21A H -0.3998 0.7820 0.0234 0.063 Uiso 1 1 calc R . . H21B H -0.2849 0.7936 -0.0076 0.063 Uiso 1 1 calc R . . H21C H -0.3326 0.8377 0.0424 0.063 Uiso 1 1 calc R . . C35 C -0.0739(4) 0.63637(16) 0.3580(3) 0.0462(10) Uani 1 1 d . . . H35A H -0.1393 0.6109 0.3399 0.069 Uiso 1 1 calc R . . H35B H -0.0876 0.6583 0.4017 0.069 Uiso 1 1 calc R . . H35C H 0.0020 0.6174 0.3782 0.069 Uiso 1 1 calc R . . C46 C -0.2210(5) 1.0474(2) 0.0160(3) 0.0668(14) Uani 1 1 d . . . H46A H -0.2339 1.0389 -0.0422 0.080 Uiso 1 1 calc R . . H46B H -0.2541 1.0831 0.0197 0.080 Uiso 1 1 calc R . . C47 C -0.0313(5) 1.0801(2) 0.0157(3) 0.0661(14) Uani 1 1 d . . . H47A H -0.0634 1.1165 0.0113 0.079 Uiso 1 1 calc R . . H47B H -0.0406 1.0665 -0.0399 0.079 Uiso 1 1 calc R . . C45 C -0.2866(5) 1.0063(2) 0.0549(3) 0.0758(16) Uani 1 1 d . . . H45A H -0.3722 1.0069 0.0265 0.114 Uiso 1 1 calc R . . H45B H -0.2745 1.0151 0.1124 0.114 Uiso 1 1 calc R . . H45C H -0.2544 0.9710 0.0506 0.114 Uiso 1 1 calc R . . C48 C 0.1008(6) 1.0804(3) 0.0633(4) 0.0887(19) Uani 1 1 d . . . H48A H 0.1451 1.1029 0.0353 0.133 Uiso 1 1 calc R . . H48B H 0.1324 1.0443 0.0672 0.133 Uiso 1 1 calc R . . H48C H 0.1097 1.0944 0.1181 0.133 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 Zn2 0.02418(18) 0.02299(17) 0.02077(16) 0.00117(15) 0.01081(13) 0.00551(15) Zn1 0.01843(16) 0.02463(18) 0.01869(15) -0.00216(15) 0.00634(12) 0.00192(14) Cl1 0.0303(4) 0.0392(4) 0.0199(3) -0.0032(3) 0.0086(3) 0.0050(3) Cl2 0.0632(6) 0.0362(5) 0.0311(4) 0.0063(4) 0.0301(4) 0.0162(4) N4 0.0219(13) 0.0241(13) 0.0191(11) -0.0008(10) 0.0067(10) 0.0011(10) C15 0.0196(13) 0.0227(14) 0.0161(12) 0.0012(11) 0.0064(10) 0.0018(11) N6 0.0206(12) 0.0228(12) 0.0204(11) -0.0006(10) 0.0059(9) 0.0034(10) C17 0.0208(14) 0.0271(16) 0.0223(13) 0.0002(12) 0.0057(11) -0.0029(12) N3 0.0172(11) 0.0253(13) 0.0195(11) -0.0013(10) 0.0058(9) 0.0010(10) N5 0.0207(12) 0.0221(13) 0.0242(12) 0.0029(10) 0.0103(10) 0.0025(10) C10 0.0217(15) 0.0258(16) 0.0227(14) 0.0005(12) 0.0047(11) -0.0020(12) C6 0.0185(14) 0.0224(14) 0.0149(12) 0.0023(11) 0.0042(10) 0.0019(11) C28 0.0208(14) 0.0243(15) 0.0157(12) 0.0022(11) 0.0069(11) 0.0050(11) N2 0.0174(12) 0.0252(13) 0.0205(11) -0.0005(10) 0.0059(9) -0.0003(10) C24 0.0248(15) 0.0290(16) 0.0225(14) 0.0005(13) 0.0067(12) 0.0063(12) C22 0.0197(15) 0.0317(17) 0.0314(16) -0.0042(14) 0.0095(13) -0.0002(13) C23 0.0197(14) 0.0229(14) 0.0195(13) -0.0031(11) 0.0061(11) 0.0008(11) C9 0.0208(15) 0.0341(18) 0.0266(15) 0.0004(14) 0.0063(12) -0.0042(13) C27 0.0269(16) 0.0301(17) 0.0222(14) -0.0044(13) 0.0107(12) 0.0041(13) C5 0.0343(18) 0.0294(17) 0.0237(15) -0.0024(13) 0.0122(13) 0.0067(14) C40 0.0237(15) 0.0206(14) 0.0232(14) 0.0049(12) 0.0068(12) 0.0013(11) C2 0.0270(16) 0.0272(16) 0.0244(15) 0.0028(13) 0.0067(12) 0.0013(13) C31 0.0248(16) 0.0308(17) 0.0230(14) 0.0026(13) 0.0076(12) -0.0010(13) C29 0.0238(15) 0.0220(14) 0.0184(13) -0.0007(11) 0.0078(11) 0.0023(11) C32 0.0250(16) 0.0258(15) 0.0239(14) -0.0013(13) 0.0073(12) -0.0022(12) C4 0.040(2) 0.0293(18) 0.0282(16) -0.0037(14) 0.0094(14) 0.0107(15) C16 0.0247(15) 0.0274(16) 0.0194(13) -0.0007(12) 0.0054(12) -0.0029(12) C12 0.0275(18) 0.039(2) 0.0393(19) 0.0015(16) 0.0098(15) -0.0069(15) C30 0.0226(15) 0.0272(16) 0.0260(15) 0.0074(13) 0.0091(12) 0.0031(12) C44 0.0201(15) 0.0391(19) 0.0326(16) 0.0000(15) 0.0095(13) -0.0031(13) C26 0.0282(16) 0.0308(18) 0.0305(16) -0.0073(14) 0.0099(13) 0.0088(14) C7 0.0207(14) 0.0205(14) 0.0195(13) 0.0001(11) 0.0054(11) 0.0001(11) C39 0.0250(16) 0.0239(15) 0.0251(15) 0.0041(13) 0.0028(12) -0.0009(12) N1 0.0177(12) 0.0256(13) 0.0190(11) -0.0027(10) 0.0055(9) 0.0018(10) C25 0.0284(17) 0.0334(19) 0.0302(16) -0.0007(14) 0.0052(13) 0.0116(14) C18 0.0201(14) 0.0255(16) 0.0184(13) 0.0013(11) 0.0049(11) 0.0006(11) C41 0.041(2) 0.0325(19) 0.0352(19) -0.0107(15) 0.0082(16) -0.0019(16) C34 0.0314(19) 0.039(2) 0.044(2) -0.0016(17) 0.0133(16) -0.0082(15) C37 0.0205(14) 0.0229(14) 0.0187(13) 0.0007(11) 0.0061(11) 0.0025(11) C14 0.0325(18) 0.0326(18) 0.0343(18) -0.0090(15) 0.0096(15) -0.0087(14) C20 0.0232(16) 0.0354(18) 0.0360(18) -0.0069(15) 0.0103(14) -0.0067(14) C8 0.0183(14) 0.0322(17) 0.0253(15) 0.0032(13) 0.0062(12) -0.0008(12) C33 0.0276(17) 0.0392(19) 0.043(2) 0.0068(16) 0.0208(16) 0.0029(15) C36 0.036(2) 0.0336(19) 0.043(2) -0.0120(17) 0.0174(17) -0.0065(15) C1 0.0182(14) 0.0210(14) 0.0223(14) -0.0011(12) 0.0055(11) 0.0000(11) C3 0.0383(19) 0.0218(16) 0.0319(17) 0.0027(14) 0.0067(15) 0.0108(14) C43 0.032(2) 0.048(2) 0.050(2) 0.0078(19) -0.0071(17) -0.0086(17) C42 0.0309(18) 0.0313(18) 0.0339(18) 0.0016(15) 0.0038(14) -0.0073(14) C11 0.0225(16) 0.043(2) 0.0317(16) -0.0017(15) 0.0128(13) -0.0016(14) C19 0.0318(18) 0.0315(18) 0.0319(17) -0.0102(14) 0.0092(14) -0.0055(14) C38 0.0292(16) 0.0217(15) 0.0231(14) -0.0002(12) 0.0061(12) 0.0017(12) C13 0.031(2) 0.049(2) 0.049(2) -0.0054(19) 0.0093(17) -0.0092(17) O1 0.059(2) 0.061(2) 0.0455(17) 0.0136(15) 0.0122(15) 0.0053(16) C21 0.0241(17) 0.065(3) 0.0343(18) -0.0111(19) 0.0039(14) -0.0052(18) C35 0.053(2) 0.036(2) 0.057(2) -0.004(2) 0.029(2) -0.008(2) C46 0.063(3) 0.079(4) 0.054(3) 0.020(3) 0.010(2) 0.031(3) C47 0.095(4) 0.058(3) 0.047(3) 0.006(2) 0.024(3) 0.001(3) C45 0.072(4) 0.095(4) 0.064(3) 0.025(3) 0.023(3) 0.011(3) C48 0.074(4) 0.081(4) 0.118(5) -0.005(4) 0.038(4) -0.012(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 Zn2 N6 1.964(2) . ? Zn2 N5 1.968(3) . ? Zn2 N4 2.105(3) . ? Zn2 Cl2 2.2476(8) . ? Zn1 N2 1.967(3) . ? Zn1 N3 1.974(2) . ? Zn1 N1 2.100(3) . ? Zn1 Cl1 2.2481(8) . ? N4 C1 1.350(4) . ? N4 C5 1.362(4) . ? C15 C6 1.391(4) . ? C15 N3 1.404(4) . ? C15 C18 1.452(4) . ? N6 C38 1.340(4) . ? N6 C37 1.389(4) . ? C17 C18 1.371(4) . ? C17 C16 1.425(4) . ? C17 C20 1.500(4) . ? N3 C16 1.331(4) . ? N5 C30 1.327(4) . ? N5 C29 1.406(3) . ? C10 C9 1.392(4) . ? C10 C7 1.431(4) . ? C10 C14 1.509(4) . ? C6 C7 1.417(4) . ? C6 C1 1.503(4) . ? C28 C29 1.405(4) . ? C28 C37 1.412(4) . ? C28 C23 1.499(4) . ? N2 C8 1.340(4) . ? N2 C7 1.396(4) . ? C24 C23 1.379(4) . ? C24 C25 1.390(4) . ? C22 C18 1.503(4) . ? C23 N1 1.356(4) . ? C9 C8 1.410(5) . ? C9 C12 1.505(5) . ? C27 N1 1.351(3) . ? C27 C26 1.374(5) . ? C5 C4 1.380(5) . ? C40 C39 1.389(4) . ? C40 C37 1.446(4) . ? C40 C44 1.499(4) . ? C2 C1 1.378(4) . ? C2 C3 1.384(4) . ? C31 C32 1.378(4) . ? C31 C30 1.418(4) . ? C31 C34 1.507(5) . ? C29 C32 1.444(4) . ? C32 C36 1.500(5) . ? C4 C3 1.377(5) . ? C16 C19 1.494(4) . ? C12 C13 1.512(5) . ? C30 C33 1.492(4) . ? C26 C25 1.384(5) . ? C39 C38 1.407(4) . ? C39 C42 1.504(5) . ? C41 C38 1.504(4) . ? C34 C35 1.525(5) . ? C20 C21 1.530(5) . ? C8 C11 1.496(4) . ? C43 C42 1.505(5) . ? O1 C46 1.387(6) . ? O1 C47 1.405(5) . ? C46 C45 1.517(7) . ? C47 C48 1.496(8) . ? 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 N6 Zn2 N5 95.87(10) . . ? N6 Zn2 N4 110.82(10) . . ? N5 Zn2 N4 116.06(10) . . ? N6 Zn2 Cl2 116.04(8) . . ? N5 Zn2 Cl2 115.70(7) . . ? N4 Zn2 Cl2 102.91(7) . . ? N2 Zn1 N3 95.58(10) . . ? N2 Zn1 N1 109.35(10) . . ? N3 Zn1 N1 119.69(9) . . ? N2 Zn1 Cl1 115.78(7) . . ? N3 Zn1 Cl1 114.09(7) . . ? N1 Zn1 Cl1 102.93(7) . . ? C1 N4 C5 117.3(3) . . ? C1 N4 Zn2 125.08(19) . . ? C5 N4 Zn2 117.7(2) . . ? C6 C15 N3 123.3(2) . . ? C6 C15 C18 129.5(3) . . ? N3 C15 C18 107.2(2) . . ? C38 N6 C37 107.8(2) . . ? C38 N6 Zn2 128.8(2) . . ? C37 N6 Zn2 122.6(2) . . ? C18 C17 C16 106.8(3) . . ? C18 C17 C20 128.7(3) . . ? C16 C17 C20 124.5(3) . . ? C16 N3 C15 107.9(2) . . ? C16 N3 Zn1 129.0(2) . . ? C15 N3 Zn1 123.10(19) . . ? C30 N5 C29 107.3(2) . . ? C30 N5 Zn2 129.0(2) . . ? C29 N5 Zn2 123.7(2) . . ? C9 C10 C7 106.6(3) . . ? C9 C10 C14 122.5(3) . . ? C7 C10 C14 130.8(3) . . ? C15 C6 C7 129.6(3) . . ? C15 C6 C1 115.2(2) . . ? C7 C6 C1 115.0(3) . . ? C29 C28 C37 129.4(2) . . ? C29 C28 C23 115.5(3) . . ? C37 C28 C23 114.9(2) . . ? C8 N2 C7 107.1(2) . . ? C8 N2 Zn1 129.1(2) . . ? C7 N2 Zn1 123.56(18) . . ? C23 C24 C25 119.6(3) . . ? N1 C23 C24 122.4(2) . . ? N1 C23 C28 117.3(3) . . ? C24 C23 C28 120.3(2) . . ? C10 C9 C8 106.4(3) . . ? C10 C9 C12 127.3(3) . . ? C8 C9 C12 126.2(3) . . ? N1 C27 C26 123.2(3) . . ? N4 C5 C4 123.0(3) . . ? C39 C40 C37 106.7(2) . . ? C39 C40 C44 122.4(3) . . ? C37 C40 C44 131.0(3) . . ? C1 C2 C3 119.8(3) . . ? C32 C31 C30 106.5(3) . . ? C32 C31 C34 128.9(3) . . ? C30 C31 C34 124.6(3) . . ? C28 C29 N5 122.3(3) . . ? C28 C29 C32 130.0(3) . . ? N5 C29 C32 107.7(2) . . ? C31 C32 C29 106.9(3) . . ? C31 C32 C36 123.6(3) . . ? C29 C32 C36 129.5(3) . . ? C3 C4 C5 118.9(3) . . ? N3 C16 C17 110.9(3) . . ? N3 C16 C19 123.2(3) . . ? C17 C16 C19 125.8(3) . . ? C9 C12 C13 114.3(3) . . ? N5 C30 C31 111.6(3) . . ? N5 C30 C33 122.2(3) . . ? C31 C30 C33 126.1(3) . . ? C27 C26 C25 119.4(3) . . ? N2 C7 C6 122.1(3) . . ? N2 C7 C10 108.4(2) . . ? C6 C7 C10 129.1(3) . . ? C40 C39 C38 106.6(3) . . ? C40 C39 C42 126.8(3) . . ? C38 C39 C42 126.5(3) . . ? C27 N1 C23 117.3(3) . . ? C27 N1 Zn1 118.7(2) . . ? C23 N1 Zn1 123.90(18) . . ? C26 C25 C24 118.2(3) . . ? C17 C18 C15 107.2(2) . . ? C17 C18 C22 122.9(3) . . ? C15 C18 C22 129.9(3) . . ? C31 C34 C35 113.3(3) . . ? N6 C37 C28 122.8(3) . . ? N6 C37 C40 107.7(3) . . ? C28 C37 C40 129.0(3) . . ? C17 C20 C21 112.6(3) . . ? N2 C8 C9 111.4(3) . . ? N2 C8 C11 121.2(3) . . ? C9 C8 C11 127.4(3) . . ? N4 C1 C2 122.3(3) . . ? N4 C1 C6 117.3(3) . . ? C2 C1 C6 120.5(3) . . ? C4 C3 C2 118.8(3) . . ? C39 C42 C43 113.7(3) . . ? N6 C38 C39 111.2(3) . . ? N6 C38 C41 121.2(3) . . ? C39 C38 C41 127.6(3) . . ? C46 O1 C47 111.8(4) . . ? O1 C46 C45 110.3(4) . . ? O1 C47 C48 109.9(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 N6 Zn2 N4 C1 62.7(3) . . . . ? N5 Zn2 N4 C1 -45.2(3) . . . . ? Cl2 Zn2 N4 C1 -172.6(2) . . . . ? N6 Zn2 N4 C5 -117.8(2) . . . . ? N5 Zn2 N4 C5 134.2(2) . . . . ? Cl2 Zn2 N4 C5 6.8(2) . . . . ? N5 Zn2 N6 C38 -172.4(3) . . . . ? N4 Zn2 N6 C38 66.8(3) . . . . ? Cl2 Zn2 N6 C38 -50.0(3) . . . . ? N5 Zn2 N6 C37 19.0(2) . . . . ? N4 Zn2 N6 C37 -101.8(2) . . . . ? Cl2 Zn2 N6 C37 141.4(2) . . . . ? C6 C15 N3 C16 -178.2(3) . . . . ? C18 C15 N3 C16 0.0(3) . . . . ? C6 C15 N3 Zn1 0.2(4) . . . . ? C18 C15 N3 Zn1 178.37(18) . . . . ? N2 Zn1 N3 C16 167.3(3) . . . . ? N1 Zn1 N3 C16 -76.7(3) . . . . ? Cl1 Zn1 N3 C16 45.8(3) . . . . ? N2 Zn1 N3 C15 -10.8(2) . . . . ? N1 Zn1 N3 C15 105.3(2) . . . . ? Cl1 Zn1 N3 C15 -132.3(2) . . . . ? N6 Zn2 N5 C30 169.0(3) . . . . ? N4 Zn2 N5 C30 -74.3(3) . . . . ? Cl2 Zn2 N5 C30 46.4(3) . . . . ? N6 Zn2 N5 C29 -8.4(2) . . . . ? N4 Zn2 N5 C29 108.2(2) . . . . ? Cl2 Zn2 N5 C29 -131.0(2) . . . . ? N3 C15 C6 C7 9.2(5) . . . . ? C18 C15 C6 C7 -168.6(3) . . . . ? N3 C15 C6 C1 -176.6(3) . . . . ? C18 C15 C6 C1 5.6(4) . . . . ? N3 Zn1 N2 C8 -168.8(3) . . . . ? N1 Zn1 N2 C8 67.0(3) . . . . ? Cl1 Zn1 N2 C8 -48.6(3) . . . . ? N3 Zn1 N2 C7 17.7(2) . . . . ? N1 Zn1 N2 C7 -106.5(2) . . . . ? Cl1 Zn1 N2 C7 137.9(2) . . . . ? C25 C24 C23 N1 1.0(5) . . . . ? C25 C24 C23 C28 -177.2(3) . . . . ? C29 C28 C23 N1 83.7(3) . . . . ? C37 C28 C23 N1 -100.6(3) . . . . ? C29 C28 C23 C24 -98.0(3) . . . . ? C37 C28 C23 C24 77.8(4) . . . . ? C7 C10 C9 C8 -3.4(4) . . . . ? C14 C10 C9 C8 175.8(3) . . . . ? C7 C10 C9 C12 174.4(3) . . . . ? C14 C10 C9 C12 -6.3(5) . . . . ? C1 N4 C5 C4 -0.5(5) . . . . ? Zn2 N4 C5 C4 -180.0(3) . . . . ? C37 C28 C29 N5 8.7(5) . . . . ? C23 C28 C29 N5 -176.2(3) . . . . ? C37 C28 C29 C32 -171.1(3) . . . . ? C23 C28 C29 C32 3.9(5) . . . . ? C30 N5 C29 C28 179.1(3) . . . . ? Zn2 N5 C29 C28 -3.0(4) . . . . ? C30 N5 C29 C32 -1.0(3) . . . . ? Zn2 N5 C29 C32 176.9(2) . . . . ? C30 C31 C32 C29 -0.1(3) . . . . ? C34 C31 C32 C29 -179.9(3) . . . . ? C30 C31 C32 C36 178.4(3) . . . . ? C34 C31 C32 C36 -1.4(5) . . . . ? C28 C29 C32 C31 -179.4(3) . . . . ? N5 C29 C32 C31 0.7(3) . . . . ? C28 C29 C32 C36 2.2(6) . . . . ? N5 C29 C32 C36 -177.7(3) . . . . ? N4 C5 C4 C3 0.9(6) . . . . ? C15 N3 C16 C17 0.5(3) . . . . ? Zn1 N3 C16 C17 -177.8(2) . . . . ? C15 N3 C16 C19 -179.2(3) . . . . ? Zn1 N3 C16 C19 2.5(4) . . . . ? C18 C17 C16 N3 -0.7(4) . . . . ? C20 C17 C16 N3 177.9(3) . . . . ? C18 C17 C16 C19 178.9(3) . . . . ? C20 C17 C16 C19 -2.5(5) . . . . ? C10 C9 C12 C13 96.2(4) . . . . ? C8 C9 C12 C13 -86.4(4) . . . . ? C29 N5 C30 C31 1.0(3) . . . . ? Zn2 N5 C30 C31 -176.8(2) . . . . ? C29 N5 C30 C33 -178.8(3) . . . . ? Zn2 N5 C30 C33 3.4(4) . . . . ? C32 C31 C30 N5 -0.5(4) . . . . ? C34 C31 C30 N5 179.3(3) . . . . ? C32 C31 C30 C33 179.3(3) . . . . ? C34 C31 C30 C33 -0.9(5) . . . . ? N1 C27 C26 C25 1.2(5) . . . . ? C8 N2 C7 C6 170.8(3) . . . . ? Zn1 N2 C7 C6 -14.4(4) . . . . ? C8 N2 C7 C10 -2.1(3) . . . . ? Zn1 N2 C7 C10 172.7(2) . . . . ? C15 C6 C7 N2 -1.4(5) . . . . ? C1 C6 C7 N2 -175.6(3) . . . . ? C15 C6 C7 C10 169.9(3) . . . . ? C1 C6 C7 C10 -4.3(4) . . . . ? C9 C10 C7 N2 3.4(3) . . . . ? C14 C10 C7 N2 -175.7(3) . . . . ? C9 C10 C7 C6 -168.8(3) . . . . ? C14 C10 C7 C6 12.0(6) . . . . ? C37 C40 C39 C38 -1.8(3) . . . . ? C44 C40 C39 C38 178.1(3) . . . . ? C37 C40 C39 C42 174.0(3) . . . . ? C44 C40 C39 C42 -6.1(5) . . . . ? C26 C27 N1 C23 -0.8(5) . . . . ? C26 C27 N1 Zn1 175.9(3) . . . . ? C24 C23 N1 C27 -0.3(4) . . . . ? C28 C23 N1 C27 178.0(3) . . . . ? C24 C23 N1 Zn1 -176.8(2) . . . . ? C28 C23 N1 Zn1 1.5(4) . . . . ? N2 Zn1 N1 C27 -115.3(2) . . . . ? N3 Zn1 N1 C27 136.1(2) . . . . ? Cl1 Zn1 N1 C27 8.3(2) . . . . ? N2 Zn1 N1 C23 61.2(2) . . . . ? N3 Zn1 N1 C23 -47.4(3) . . . . ? Cl1 Zn1 N1 C23 -175.2(2) . . . . ? C27 C26 C25 C24 -0.4(5) . . . . ? C23 C24 C25 C26 -0.7(5) . . . . ? C16 C17 C18 C15 0.7(3) . . . . ? C20 C17 C18 C15 -177.9(3) . . . . ? C16 C17 C18 C22 178.2(3) . . . . ? C20 C17 C18 C22 -0.3(5) . . . . ? C6 C15 C18 C17 177.6(3) . . . . ? N3 C15 C18 C17 -0.4(3) . . . . ? C6 C15 C18 C22 0.3(5) . . . . ? N3 C15 C18 C22 -177.7(3) . . . . ? C32 C31 C34 C35 98.8(4) . . . . ? C30 C31 C34 C35 -81.0(4) . . . . ? C38 N6 C37 C28 170.1(3) . . . . ? Zn2 N6 C37 C28 -19.2(4) . . . . ? C38 N6 C37 C40 -2.4(3) . . . . ? Zn2 N6 C37 C40 168.30(19) . . . . ? C29 C28 C37 N6 3.5(5) . . . . ? C23 C28 C37 N6 -171.6(3) . . . . ? C29 C28 C37 C40 174.2(3) . . . . ? C23 C28 C37 C40 -0.8(4) . . . . ? C39 C40 C37 N6 2.6(3) . . . . ? C44 C40 C37 N6 -177.3(3) . . . . ? C39 C40 C37 C28 -169.3(3) . . . . ? C44 C40 C37 C28 10.8(5) . . . . ? C18 C17 C20 C21 85.7(4) . . . . ? C16 C17 C20 C21 -92.6(4) . . . . ? C7 N2 C8 C9 -0.1(4) . . . . ? Zn1 N2 C8 C9 -174.4(2) . . . . ? C7 N2 C8 C11 -178.2(3) . . . . ? Zn1 N2 C8 C11 7.4(4) . . . . ? C10 C9 C8 N2 2.2(4) . . . . ? C12 C9 C8 N2 -175.6(3) . . . . ? C10 C9 C8 C11 -179.8(3) . . . . ? C12 C9 C8 C11 2.4(6) . . . . ? C5 N4 C1 C2 -0.3(4) . . . . ? Zn2 N4 C1 C2 179.2(2) . . . . ? C5 N4 C1 C6 -179.8(3) . . . . ? Zn2 N4 C1 C6 -0.3(4) . . . . ? C3 C2 C1 N4 0.7(5) . . . . ? C3 C2 C1 C6 -179.9(3) . . . . ? C15 C6 C1 N4 87.0(3) . . . . ? C7 C6 C1 N4 -97.9(3) . . . . ? C15 C6 C1 C2 -92.4(3) . . . . ? C7 C6 C1 C2 82.6(4) . . . . ? C5 C4 C3 C2 -0.5(5) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C40 C39 C42 C43 -80.0(4) . . . . ? C38 C39 C42 C43 95.0(4) . . . . ? C37 N6 C38 C39 1.3(3) . . . . ? Zn2 N6 C38 C39 -168.6(2) . . . . ? C37 N6 C38 C41 -176.7(3) . . . . ? Zn2 N6 C38 C41 13.4(4) . . . . ? C40 C39 C38 N6 0.3(4) . . . . ? C42 C39 C38 N6 -175.4(3) . . . . ? C40 C39 C38 C41 178.2(3) . . . . ? C42 C39 C38 C41 2.4(5) . . . . ? C47 O1 C46 C45 172.9(4) . . . . ? C46 O1 C47 C48 177.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 35.11 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.917 _refine_diff_density_min -1.965 _refine_diff_density_rms 0.119 data_sja3_01 _database_code_depnum_ccdc_archive 'CCDC 234541' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H58 N6 O6 S2 Zn2' _chemical_formula_weight 985.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' S S 0.1246 0.1234 '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' H H 0.0000 0.0000 '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 12.9761(19) _cell_length_b 8.9847(8) _cell_length_c 19.804(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.061(11) _cell_angle_gamma 90.00 _cell_volume 2286.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 1.195 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Stoe IPDSII image plate' _diffrn_measurement_method '135 frames at 1^o intervals, exposure time 1 minutes' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28786 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0754 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 33.53 _reflns_number_total 8884 _reflns_number_gt 4827 _reflns_threshold_expression >2sigma(I) _computing_data_collection X-AREA _computing_cell_refinement X-AREA _computing_data_reduction X-RED _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP II (Johnson, 1976)' _computing_publication_material 'SHELXL 97 (Sheldrick, 1997)' _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^)+(0.0938P)^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 0.0074(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8884 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1532 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 0.878 _refine_ls_restrained_S_all 0.878 _refine_ls_shift/su_max 0.034 _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 Zn1 Zn 0.45183(2) 0.97696(3) 0.120565(15) 0.02854(9) Uani 1 1 d . . . S1 S 0.38906(7) 0.82719(8) 0.25743(4) 0.0464(2) Uani 1 1 d . . . C7 C 0.57325(19) 0.7966(3) 0.03338(12) 0.0287(5) Uani 1 1 d . . . C6 C 0.5165(2) 1.2176(3) 0.01542(12) 0.0278(5) Uani 1 1 d . . . N3 N 0.35182(17) 0.8938(2) 0.04774(11) 0.0317(4) Uani 1 1 d . . . C15 C 0.3797(2) 0.8214(3) -0.00963(13) 0.0297(5) Uani 1 1 d . . . O3 O 0.4747(3) 0.7352(3) 0.28547(15) 0.0718(8) Uani 1 1 d . . . C10 C 0.6759(2) 0.7345(4) 0.03288(15) 0.0404(6) Uani 1 1 d . . . C17 C 0.2031(2) 0.8402(3) -0.02230(16) 0.0382(6) Uani 1 1 d . . . C5 C 0.4452(3) 1.2686(3) 0.18792(14) 0.0396(6) Uani 1 1 d . . . H5 H 0.4222 1.2089 0.2212 0.048 Uiso 1 1 calc R . . C19 C 0.1925(3) 0.9778(4) 0.0923(2) 0.0553(9) Uani 1 1 d . . . H19A H 0.2149 1.0794 0.0980 0.066 Uiso 1 1 calc R . . H19B H 0.2081 0.9261 0.1349 0.066 Uiso 1 1 calc R . . H19C H 0.1188 0.9750 0.0775 0.066 Uiso 1 1 calc R . . O1 O 0.4240(2) 0.9446(3) 0.21399(11) 0.0558(7) Uani 1 1 d . . . C3 C 0.4940(3) 1.5072(3) 0.15172(17) 0.0484(8) Uani 1 1 d . . . H3 H 0.5051 1.6084 0.1593 0.058 Uiso 1 1 calc R . . C1 C 0.4997(2) 1.2904(3) 0.08146(13) 0.0314(5) Uani 1 1 d . . . N2 N 0.57141(17) 0.8672(2) 0.09639(11) 0.0300(4) Uani 1 1 d . . . C4 C 0.4561(3) 1.4189(3) 0.20024(16) 0.0488(8) Uani 1 1 d . . . H4 H 0.4385 1.4603 0.2401 0.059 Uiso 1 1 calc R . . C11 C 0.6902(3) 0.9105(6) 0.20352(19) 0.0661(11) Uani 1 1 d . . . H11A H 0.6440 0.8674 0.2319 0.079 Uiso 1 1 calc R . . H11B H 0.6817 1.0167 0.2025 0.079 Uiso 1 1 calc R . . H11C H 0.7608 0.8863 0.2215 0.079 Uiso 1 1 calc R . . N1 N 0.46639(17) 1.2031(2) 0.12974(10) 0.0299(4) Uani 1 1 d . . . C16 C 0.2478(2) 0.9046(3) 0.04006(16) 0.0377(6) Uani 1 1 d . . . C20 C 0.0885(2) 0.8213(4) -0.04381(19) 0.0467(7) Uani 1 1 d . . . H20A H 0.0736 0.8287 -0.0931 0.056 Uiso 1 1 calc R . . H20B H 0.0516 0.9010 -0.0244 0.056 Uiso 1 1 calc R . . C14 C 0.7190(3) 0.6438(4) -0.02054(17) 0.0512(8) Uani 1 1 d . . . H14A H 0.7146 0.7001 -0.0620 0.061 Uiso 1 1 calc R . . H14B H 0.6795 0.5537 -0.0287 0.061 Uiso 1 1 calc R . . H14C H 0.7905 0.6197 -0.0049 0.061 Uiso 1 1 calc R . . C21 C 0.0493(3) 0.6722(4) -0.0211(2) 0.0571(9) Uani 1 1 d . . . H21A H 0.0635 0.6648 0.0277 0.068 Uiso 1 1 calc R . . H21B H 0.0841 0.5929 -0.0413 0.068 Uiso 1 1 calc R . . H21C H -0.0244 0.6649 -0.0354 0.068 Uiso 1 1 calc R . . C8 C 0.6657(2) 0.8505(4) 0.13329(16) 0.0446(7) Uani 1 1 d . . . C18 C 0.2838(2) 0.7898(3) -0.05487(14) 0.0354(5) Uani 1 1 d . . . C9 C 0.7317(3) 0.7652(5) 0.09610(19) 0.0588(10) Uani 1 1 d . . . C2 C 0.5150(3) 1.4419(3) 0.09170(15) 0.0425(7) Uani 1 1 d . . . H2 H 0.5394 1.4997 0.0583 0.051 Uiso 1 1 calc R . . C22 C 0.2679(3) 0.7153(5) -0.12322(17) 0.0517(8) Uani 1 1 d . . . H22A H 0.2955 0.6161 -0.1190 0.062 Uiso 1 1 calc R . . H22B H 0.3031 0.7709 -0.1545 0.062 Uiso 1 1 calc R . . H22C H 0.1948 0.7113 -0.1400 0.062 Uiso 1 1 calc R . . O2 O 0.2999(3) 0.7496(4) 0.2230(2) 0.0958(12) Uani 1 1 d . . . C23 C 0.3474(4) 0.9306(5) 0.3241(2) 0.0689(12) Uani 1 1 d . . . H23A H 0.4037 0.9911 0.3454 0.083 Uiso 1 1 calc R . . H23B H 0.3256 0.8638 0.3572 0.083 Uiso 1 1 calc R . . H23C H 0.2901 0.9932 0.3061 0.083 Uiso 1 1 calc R . . C12 C 0.8424(4) 0.7030(6) 0.1291(3) 0.0809(14) Uani 1 1 d . . . H12A H 0.8433 0.6813 0.1771 0.097 Uiso 1 1 calc R . . H12B H 0.8602 0.6134 0.1060 0.097 Uiso 1 1 calc R . . C13 C 0.9108(6) 0.8189(6) 0.1197(3) 0.0995(18) Uani 1 1 d . . . H13A H 0.8924 0.9057 0.1437 0.119 Uiso 1 1 calc R . . H13B H 0.9064 0.8410 0.0720 0.119 Uiso 1 1 calc R . . H13C H 0.9807 0.7896 0.1371 0.119 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 Zn1 0.03385(15) 0.02724(14) 0.02575(14) -0.00203(11) 0.00842(10) -0.00064(12) S1 0.0697(5) 0.0355(3) 0.0370(4) 0.0024(3) 0.0174(4) -0.0043(3) C7 0.0319(12) 0.0289(11) 0.0265(11) 0.0006(8) 0.0083(10) -0.0005(9) C6 0.0361(13) 0.0235(10) 0.0246(10) 0.0007(8) 0.0074(9) -0.0044(9) N3 0.0294(10) 0.0320(10) 0.0336(11) -0.0018(8) 0.0041(9) -0.0008(8) C15 0.0324(12) 0.0286(11) 0.0283(11) 0.0003(9) 0.0043(10) -0.0048(9) O3 0.104(2) 0.0507(15) 0.0596(16) -0.0037(13) 0.0063(16) 0.0231(15) C10 0.0328(13) 0.0542(17) 0.0351(14) -0.0029(12) 0.0071(11) 0.0061(12) C17 0.0347(13) 0.0337(13) 0.0450(15) -0.0004(11) 0.0015(12) -0.0018(10) C5 0.0585(18) 0.0337(13) 0.0287(12) -0.0006(10) 0.0140(12) 0.0014(12) C19 0.0373(15) 0.063(2) 0.066(2) -0.0213(18) 0.0076(15) 0.0034(15) O1 0.0908(19) 0.0480(13) 0.0353(11) 0.0017(9) 0.0318(12) -0.0055(12) C3 0.077(2) 0.0292(14) 0.0397(16) -0.0063(11) 0.0102(16) -0.0016(13) C1 0.0361(13) 0.0309(11) 0.0274(11) -0.0015(9) 0.0052(10) -0.0013(10) N2 0.0308(10) 0.0327(10) 0.0268(10) -0.0025(8) 0.0056(8) 0.0018(8) C4 0.080(2) 0.0356(14) 0.0326(14) -0.0067(11) 0.0156(15) 0.0026(15) C11 0.051(2) 0.099(3) 0.0433(19) -0.020(2) -0.0093(16) 0.012(2) N1 0.0355(11) 0.0283(10) 0.0262(10) -0.0019(7) 0.0055(9) -0.0006(8) C16 0.0337(13) 0.0347(13) 0.0447(15) -0.0035(11) 0.0051(12) 0.0006(10) C20 0.0350(14) 0.0448(16) 0.0583(19) -0.0050(14) -0.0004(14) 0.0023(12) C14 0.0436(16) 0.069(2) 0.0417(16) -0.0076(15) 0.0092(14) 0.0176(15) C21 0.0370(16) 0.0520(19) 0.083(3) -0.0075(18) 0.0129(17) -0.0091(14) C8 0.0370(14) 0.0610(19) 0.0343(14) -0.0069(13) 0.0003(12) 0.0070(13) C18 0.0346(13) 0.0364(13) 0.0340(13) 0.0024(10) 0.0007(11) -0.0053(10) C9 0.0361(16) 0.093(3) 0.0459(18) -0.0184(19) -0.0006(14) 0.0143(17) C2 0.0642(19) 0.0304(13) 0.0347(14) -0.0006(10) 0.0131(14) -0.0043(12) C22 0.0447(17) 0.070(2) 0.0391(16) -0.0135(15) 0.0015(14) -0.0125(15) O2 0.109(3) 0.067(2) 0.104(3) 0.0046(19) -0.013(2) -0.0394(19) C23 0.088(3) 0.076(3) 0.053(2) 0.0060(18) 0.045(2) 0.011(2) C12 0.081(3) 0.085(3) 0.084(3) -0.021(3) 0.036(3) -0.011(3) C13 0.150(5) 0.073(3) 0.078(4) 0.013(3) 0.026(4) 0.018(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 Zn1 N3 1.949(2) . ? Zn1 N2 1.954(2) . ? Zn1 O1 1.956(2) . ? Zn1 N1 2.047(2) . ? S1 O3 1.433(3) . ? S1 O2 1.439(3) . ? S1 O1 1.473(2) . ? S1 C23 1.761(4) . ? C7 N2 1.403(3) . ? C7 C6 1.411(4) 3_675 ? C7 C10 1.445(4) . ? C6 C7 1.411(4) 3_675 ? C6 C15 1.412(3) 3_675 ? C6 C1 1.505(3) . ? N3 C16 1.341(3) . ? N3 C15 1.400(3) . ? C15 C6 1.412(3) 3_675 ? C15 C18 1.456(4) . ? C10 C9 1.383(5) . ? C10 C14 1.504(4) . ? C17 C18 1.380(4) . ? C17 C16 1.412(4) . ? C17 C20 1.498(4) . ? C5 N1 1.356(3) . ? C5 C4 1.376(4) . ? C19 C16 1.492(4) . ? C3 C2 1.386(4) . ? C3 C4 1.388(5) . ? C1 N1 1.353(3) . ? C1 C2 1.387(4) . ? N2 C8 1.343(4) . ? C11 C8 1.484(5) . ? C20 C21 1.523(5) . ? C8 C9 1.429(4) . ? C18 C22 1.498(4) . ? C9 C12 1.594(7) . ? C12 C13 1.397(7) . ? 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 N3 Zn1 N2 95.42(9) . . ? N3 Zn1 O1 116.81(11) . . ? N2 Zn1 O1 114.52(11) . . ? N3 Zn1 N1 119.33(9) . . ? N2 Zn1 N1 117.15(9) . . ? O1 Zn1 N1 95.20(9) . . ? O3 S1 O2 115.6(2) . . ? O3 S1 O1 110.75(18) . . ? O2 S1 O1 111.31(19) . . ? O3 S1 C23 108.5(2) . . ? O2 S1 C23 107.5(2) . . ? O1 S1 C23 102.28(17) . . ? N2 C7 C6 122.3(2) . 3_675 ? N2 C7 C10 108.1(2) . . ? C6 C7 C10 129.3(2) 3_675 . ? C7 C6 C15 128.8(2) 3_675 3_675 ? C7 C6 C1 115.4(2) 3_675 . ? C15 C6 C1 115.7(2) 3_675 . ? C16 N3 C15 108.2(2) . . ? C16 N3 Zn1 127.72(19) . . ? C15 N3 Zn1 123.90(17) . . ? N3 C15 C6 122.6(2) . 3_675 ? N3 C15 C18 107.1(2) . . ? C6 C15 C18 130.2(2) 3_675 . ? C9 C10 C7 106.4(2) . . ? C9 C10 C14 123.1(3) . . ? C7 C10 C14 130.4(3) . . ? C18 C17 C16 107.3(3) . . ? C18 C17 C20 128.1(3) . . ? C16 C17 C20 124.4(3) . . ? N1 C5 C4 123.3(3) . . ? S1 O1 Zn1 140.54(16) . . ? C2 C3 C4 118.9(3) . . ? N1 C1 C2 121.3(2) . . ? N1 C1 C6 117.5(2) . . ? C2 C1 C6 121.2(2) . . ? C8 N2 C7 107.8(2) . . ? C8 N2 Zn1 128.10(19) . . ? C7 N2 Zn1 124.01(17) . . ? C5 C4 C3 118.4(3) . . ? C1 N1 C5 118.2(2) . . ? C1 N1 Zn1 123.18(16) . . ? C5 N1 Zn1 118.62(17) . . ? N3 C16 C17 110.7(2) . . ? N3 C16 C19 121.9(3) . . ? C17 C16 C19 127.5(3) . . ? C17 C20 C21 112.0(3) . . ? N2 C8 C9 110.2(3) . . ? N2 C8 C11 121.9(3) . . ? C9 C8 C11 127.8(3) . . ? C17 C18 C15 106.7(2) . . ? C17 C18 C22 123.5(3) . . ? C15 C18 C22 129.8(3) . . ? C10 C9 C8 107.3(3) . . ? C10 C9 C12 128.9(3) . . ? C8 C9 C12 123.2(3) . . ? C3 C2 C1 120.0(3) . . ? C13 C12 C9 103.7(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Zn1 N3 C16 168.8(2) . . . . ? O1 Zn1 N3 C16 47.8(3) . . . . ? N1 Zn1 N3 C16 -65.8(3) . . . . ? N2 Zn1 N3 C15 -16.9(2) . . . . ? O1 Zn1 N3 C15 -137.9(2) . . . . ? N1 Zn1 N3 C15 108.5(2) . . . . ? C16 N3 C15 C6 -175.2(2) . . . 3_675 ? Zn1 N3 C15 C6 9.5(3) . . . 3_675 ? C16 N3 C15 C18 1.1(3) . . . . ? Zn1 N3 C15 C18 -174.21(17) . . . . ? N2 C7 C10 C9 1.9(4) . . . . ? C6 C7 C10 C9 -172.4(3) 3_675 . . . ? N2 C7 C10 C14 177.7(3) . . . . ? C6 C7 C10 C14 3.4(5) 3_675 . . . ? O3 S1 O1 Zn1 84.5(3) . . . . ? O2 S1 O1 Zn1 -45.6(4) . . . . ? C23 S1 O1 Zn1 -160.1(3) . . . . ? N3 Zn1 O1 S1 42.5(3) . . . . ? N2 Zn1 O1 S1 -67.8(3) . . . . ? N1 Zn1 O1 S1 169.2(3) . . . . ? C7 C6 C1 N1 84.2(3) 3_675 . . . ? C15 C6 C1 N1 -98.4(3) 3_675 . . . ? C7 C6 C1 C2 -94.1(3) 3_675 . . . ? C15 C6 C1 C2 83.4(3) 3_675 . . . ? C6 C7 N2 C8 174.5(3) 3_675 . . . ? C10 C7 N2 C8 -0.3(3) . . . . ? C6 C7 N2 Zn1 -8.3(3) 3_675 . . . ? C10 C7 N2 Zn1 176.88(18) . . . . ? N3 Zn1 N2 C8 -167.0(3) . . . . ? O1 Zn1 N2 C8 -44.3(3) . . . . ? N1 Zn1 N2 C8 66.0(3) . . . . ? N3 Zn1 N2 C7 16.4(2) . . . . ? O1 Zn1 N2 C7 139.15(19) . . . . ? N1 Zn1 N2 C7 -110.6(2) . . . . ? N1 C5 C4 C3 -2.3(6) . . . . ? C2 C3 C4 C5 2.8(6) . . . . ? C2 C1 N1 C5 2.0(4) . . . . ? C6 C1 N1 C5 -176.3(3) . . . . ? C2 C1 N1 Zn1 -175.7(2) . . . . ? C6 C1 N1 Zn1 6.1(3) . . . . ? C4 C5 N1 C1 -0.1(5) . . . . ? C4 C5 N1 Zn1 177.6(3) . . . . ? N3 Zn1 N1 C1 -63.7(2) . . . . ? N2 Zn1 N1 C1 50.5(2) . . . . ? O1 Zn1 N1 C1 171.5(2) . . . . ? N3 Zn1 N1 C5 118.7(2) . . . . ? N2 Zn1 N1 C5 -127.1(2) . . . . ? O1 Zn1 N1 C5 -6.1(2) . . . . ? C15 N3 C16 C17 -0.1(3) . . . . ? Zn1 N3 C16 C17 174.97(19) . . . . ? C15 N3 C16 C19 -179.4(3) . . . . ? Zn1 N3 C16 C19 -4.4(4) . . . . ? C18 C17 C16 N3 -1.0(3) . . . . ? C20 C17 C16 N3 174.3(3) . . . . ? C18 C17 C16 C19 178.3(3) . . . . ? C20 C17 C16 C19 -6.4(5) . . . . ? C18 C17 C20 C21 84.1(4) . . . . ? C16 C17 C20 C21 -90.2(4) . . . . ? C7 N2 C8 C9 -1.4(4) . . . . ? Zn1 N2 C8 C9 -178.4(3) . . . . ? C7 N2 C8 C11 -179.1(3) . . . . ? Zn1 N2 C8 C11 3.9(5) . . . . ? C16 C17 C18 C15 1.6(3) . . . . ? C20 C17 C18 C15 -173.5(3) . . . . ? C16 C17 C18 C22 -179.5(3) . . . . ? C20 C17 C18 C22 5.4(5) . . . . ? N3 C15 C18 C17 -1.7(3) . . . . ? C6 C15 C18 C17 174.2(3) 3_675 . . . ? N3 C15 C18 C22 179.5(3) . . . . ? C6 C15 C18 C22 -4.6(5) 3_675 . . . ? C7 C10 C9 C8 -2.6(4) . . . . ? C14 C10 C9 C8 -178.8(3) . . . . ? C7 C10 C9 C12 169.5(4) . . . . ? C14 C10 C9 C12 -6.7(7) . . . . ? N2 C8 C9 C10 2.6(5) . . . . ? C11 C8 C9 C10 -179.8(4) . . . . ? N2 C8 C9 C12 -170.1(4) . . . . ? C11 C8 C9 C12 7.5(7) . . . . ? C4 C3 C2 C1 -1.0(6) . . . . ? N1 C1 C2 C3 -1.4(5) . . . . ? C6 C1 C2 C3 176.8(3) . . . . ? C10 C9 C12 C13 100.7(6) . . . . ? C8 C9 C12 C13 -88.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 33.53 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.200 _refine_diff_density_min -0.934 _refine_diff_density_rms 0.110