# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_comp2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H37 N6 O11 Zn2' _chemical_formula_weight 836.44 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' Zn Zn 0.2839 1.4301 '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 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9316(4) _cell_length_b 11.5548(3) _cell_length_c 20.3743(10) _cell_angle_alpha 87.909(3) _cell_angle_beta 80.351(4) _cell_angle_gamma 75.405(3) _cell_volume 1781.41(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6491 _cell_measurement_theta_min 4.2 _cell_measurement_theta_max 25.4 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 862 _exptl_absorpt_coefficient_mu 1.416 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.724 _exptl_absorpt_correction_T_max 0.770 _exptl_absorpt_process_details ? _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11773 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.16 _diffrn_reflns_theta_max 25.35 _reflns_number_total 6491 _reflns_number_gt 4259 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 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^)+(0.0408P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6491 _refine_ls_number_parameters 490 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0824 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_restrained_S_all 0.905 _refine_ls_shift/su_max 0.002 _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 Zn1 Zn -0.12485(5) 1.15873(3) 0.654978(18) 0.03199(12) Uani 1 1 d . . . Zn2 Zn 0.42436(5) 0.20782(3) 0.745788(18) 0.03272(12) Uani 1 1 d . . . C1 C 0.2288(4) 0.2041(3) 0.88051(17) 0.0384(8) Uani 1 1 d . . . H1 H 0.2703 0.2672 0.8928 0.046 Uiso 1 1 calc R . . C2 C 0.1660(5) 0.0748(3) 0.8264(2) 0.0489(10) Uani 1 1 d . . . H2 H 0.1575 0.0294 0.7909 0.059 Uiso 1 1 calc R . . C3 C 0.0973(5) 0.1541(3) 0.99455(17) 0.0467(9) Uani 1 1 d . . . H3A H 0.0109 0.1093 1.0113 0.056 Uiso 1 1 calc R . . H3B H 0.0461 0.2373 1.0070 0.056 Uiso 1 1 calc R . . C4 C 0.2602(6) 0.1075(4) 1.0255(2) 0.0691(12) Uani 1 1 d . . . H4A H 0.3063 0.0230 1.0151 0.083 Uiso 1 1 calc R . . H4B H 0.3494 0.1482 1.0059 0.083 Uiso 1 1 calc R . . C5 C 0.2281(7) 0.1239(4) 1.0997(2) 0.0841(15) Uani 1 1 d . . . H5A H 0.1522 0.0739 1.1198 0.101 Uiso 1 1 calc R . . H5B H 0.1664 0.2064 1.1104 0.101 Uiso 1 1 calc R . . C6 C 0.3972(8) 0.0930(5) 1.1299(3) 0.111(2) Uani 1 1 d . . . C7 C 0.4773(13) 0.1869(8) 1.1368(5) 0.071(3) Uani 0.50 1 d P . . C7' C 0.4019(18) 0.1282(12) 1.1931(6) 0.130(5) Uani 0.50 1 d PD . . C8 C 0.3818(8) 0.2757(5) 1.1992(3) 0.0959(17) Uani 1 1 d . . . C9 C 0.3818(10) 0.2444(7) 1.2703(5) 0.140(3) Uani 1 1 d D . . H9A H 0.3250 0.1793 1.2804 0.167 Uiso 1 1 calc R . . H9B H 0.5032 0.2157 1.2774 0.167 Uiso 1 1 calc R . . C10 C 0.2938(9) 0.3419(8) 1.3164(3) 0.126(3) Uani 1 1 d D . . H10A H 0.1754 0.3776 1.3076 0.152 Uiso 1 1 calc R . . H10B H 0.3591 0.4031 1.3124 0.152 Uiso 1 1 calc R . . C11 C 0.2864(8) 0.2780(6) 1.3974(5) 0.165(4) Uani 1 1 d D . . H11A H 0.2316 0.2113 1.4026 0.197 Uiso 1 1 calc R . . H11B H 0.4002 0.2565 1.4123 0.197 Uiso 1 1 calc R . . C12 C 0.1867(9) 0.3741(5) 1.4226(4) 0.148(3) Uani 1 1 d . . . H12A H 0.0788 0.4003 1.4038 0.177 Uiso 1 1 calc R . . H12B H 0.2456 0.4383 1.4218 0.177 Uiso 1 1 calc R . . C13 C 0.0561(5) 0.2354(3) 1.5245(2) 0.0570(11) Uani 1 1 d . . . H13 H 0.0137 0.1885 1.4983 0.068 Uiso 1 1 calc R . . C14 C 0.1170(5) 0.3172(3) 1.6033(2) 0.0503(10) Uani 1 1 d . . . H14 H 0.1204 0.3380 1.6467 0.060 Uiso 1 1 calc R . . C15 C 0.3631(4) -0.0549(3) 0.50309(17) 0.0398(8) Uani 1 1 d . . . H20 H 0.2704 -0.0915 0.5055 0.048 Uiso 1 1 calc R . . C16 C 0.3887(4) -0.0025(3) 0.55949(17) 0.0391(8) Uani 1 1 d . . . H19 H 0.3136 -0.0045 0.5996 0.047 Uiso 1 1 calc R . . C17 C 0.5261(4) 0.0530(2) 0.55637(16) 0.0311(8) Uani 1 1 d . . . C18 C 0.5516(4) 0.1100(2) 0.61782(17) 0.0321(8) Uani 1 1 d . . . C19 C 0.2425(4) 0.5745(2) 0.72733(16) 0.0337(8) Uani 1 1 d . . . C20 C 0.2559(4) 0.5941(3) 0.65960(17) 0.0392(8) Uani 1 1 d . . . H6 H 0.3103 0.5310 0.6302 0.047 Uiso 1 1 calc R . . C21 C 0.1895(4) 0.7061(3) 0.63497(17) 0.0396(8) Uani 1 1 d . . . H7 H 0.2007 0.7182 0.5892 0.047 Uiso 1 1 calc R . . C22 C 0.1056(4) 0.8014(2) 0.67861(16) 0.0334(8) Uani 1 1 d . . . C23 C 0.0970(5) 0.7816(3) 0.74610(16) 0.0409(9) Uani 1 1 d . . . H3 H 0.0457 0.8452 0.7756 0.049 Uiso 1 1 calc R . . C24 C 0.1627(5) 0.6698(3) 0.77083(17) 0.0420(9) Uani 1 1 d . . . H4 H 0.1537 0.6580 0.8166 0.050 Uiso 1 1 calc R . . C25 C 0.3095(4) 0.4521(3) 0.75370(17) 0.0360(8) Uani 1 1 d . . . C26 C 0.0218(4) 0.9213(3) 0.65197(18) 0.0335(8) Uani 1 1 d . . . C27 C 0.7509(4) 0.3124(2) 0.84579(16) 0.0320(7) Uani 1 1 d . . . C28 C 0.6715(5) 0.2780(3) 0.90609(17) 0.0401(8) Uani 1 1 d . . . H28 H 0.6144 0.2166 0.9078 0.048 Uiso 1 1 calc R . . C29 C 0.6762(5) 0.3349(3) 0.96453(17) 0.0441(9) Uani 1 1 d . . . H29 H 0.6263 0.3096 1.0054 0.053 Uiso 1 1 calc R . . C30 C 0.7551(4) 0.4287(3) 0.96174(16) 0.0359(8) Uani 1 1 d . . . C31 C 0.8366(5) 0.4622(3) 0.90151(17) 0.0427(9) Uani 1 1 d . . . H31 H 0.8919 0.5245 0.8999 0.051 Uiso 1 1 calc R . . C32 C 0.8365(4) 0.4037(3) 0.84361(17) 0.0404(8) Uani 1 1 d . . . H32 H 0.8939 0.4256 0.8032 0.048 Uiso 1 1 calc R . . C33 C 0.7414(4) 0.2524(3) 0.78310(17) 0.0337(8) Uani 1 1 d . . . C34 C 0.7547(5) 0.4957(3) 1.02324(18) 0.0420(9) Uani 1 1 d . . . N1 N 0.2528(3) 0.1627(2) 0.81877(13) 0.0365(7) Uani 1 1 d . . . N2 N 0.0956(4) 0.0588(3) 0.88730(17) 0.0569(9) Uani 1 1 d . . . N3 N 0.1383(4) 0.1436(2) 0.92174(14) 0.0389(7) Uani 1 1 d . . . N4 N 0.1554(6) 0.3072(4) 1.50204(18) 0.0841(13) Uani 1 1 d . . . N5 N 0.1985(5) 0.3601(3) 1.5524(2) 0.0784(12) Uani 1 1 d . . . N6 N 0.0256(3) 0.2394(2) 1.58950(13) 0.0356(6) Uani 1 1 d . . . O1 O 0.8384(3) 0.27143(18) 0.73066(12) 0.0449(6) Uani 1 1 d . . . O2 O 0.6373(3) 0.18483(17) 0.78664(11) 0.0400(6) Uani 1 1 d . . . O1W O 0.5982(8) 0.3919(4) 0.5282(3) 0.177(2) Uani 1 1 d . . . O3 O 0.7918(4) 0.5905(2) 1.02181(12) 0.0578(7) Uani 1 1 d . . . O4 O 0.7075(4) 0.4407(2) 1.07827(13) 0.0618(8) Uani 1 1 d D . . O5 O 0.3528(3) 0.36719(17) 0.71055(11) 0.0431(6) Uani 1 1 d . . . O6 O 0.3194(3) 0.43388(18) 0.81308(12) 0.0499(6) Uani 1 1 d . . . O7 O -0.0071(3) 0.93217(18) 0.59433(13) 0.0464(6) Uani 1 1 d . . . O8 O -0.0159(3) 1.00913(17) 0.69334(11) 0.0434(6) Uani 1 1 d . . . O9 O 0.6700(3) 0.16734(17) 0.61172(11) 0.0370(5) Uani 1 1 d . . . O10 O 0.4513(3) 0.09957(17) 0.67118(11) 0.0398(6) Uani 1 1 d . . . H4WA H 0.703(5) 0.488(3) 1.1106(16) 0.060 Uiso 1 1 d 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 Zn1 0.0416(2) 0.0324(2) 0.0250(2) -0.00182(15) -0.00883(18) -0.01225(16) Zn2 0.0437(3) 0.0324(2) 0.0225(2) -0.00559(15) -0.00635(18) -0.00880(16) C1 0.049(2) 0.0395(18) 0.029(2) -0.0027(15) -0.0056(17) -0.0154(16) C2 0.062(3) 0.049(2) 0.043(2) -0.0109(17) -0.008(2) -0.0253(18) C3 0.050(2) 0.057(2) 0.031(2) 0.0011(16) 0.0001(18) -0.0148(17) C4 0.070(3) 0.086(3) 0.040(3) 0.001(2) -0.008(2) -0.001(2) C5 0.095(4) 0.108(4) 0.042(3) 0.000(2) -0.012(3) -0.011(3) C6 0.129(5) 0.118(4) 0.080(4) -0.027(3) -0.059(4) 0.011(4) C7 0.086(7) 0.078(6) 0.047(6) 0.001(5) 0.002(5) -0.024(5) C7' 0.145(12) 0.157(12) 0.070(9) -0.044(8) -0.032(9) 0.008(9) C8 0.117(5) 0.098(4) 0.074(4) -0.004(3) -0.029(3) -0.022(3) C9 0.113(6) 0.159(6) 0.166(9) 0.071(6) -0.030(6) -0.074(5) C10 0.089(5) 0.245(8) 0.052(4) 0.067(5) -0.018(3) -0.060(5) C11 0.071(4) 0.095(5) 0.319(13) 0.028(6) -0.031(6) -0.010(3) C12 0.141(6) 0.072(4) 0.236(10) -0.049(5) -0.076(6) -0.002(4) C13 0.077(3) 0.069(3) 0.038(2) 0.0011(19) -0.013(2) -0.040(2) C14 0.064(3) 0.057(2) 0.040(2) -0.0026(18) -0.013(2) -0.0295(19) C15 0.039(2) 0.051(2) 0.035(2) -0.0132(16) -0.0015(17) -0.0216(16) C16 0.042(2) 0.052(2) 0.0259(19) -0.0097(15) -0.0001(16) -0.0195(16) C17 0.0329(19) 0.0327(16) 0.0285(19) -0.0098(13) -0.0064(15) -0.0071(14) C18 0.039(2) 0.0245(16) 0.031(2) -0.0091(13) -0.0091(17) -0.0014(14) C19 0.041(2) 0.0332(17) 0.0276(19) -0.0018(14) -0.0059(16) -0.0109(14) C20 0.050(2) 0.0312(17) 0.032(2) -0.0057(14) -0.0037(17) -0.0031(14) C21 0.052(2) 0.0409(19) 0.0222(19) 0.0013(14) -0.0028(16) -0.0070(16) C22 0.0353(19) 0.0324(17) 0.032(2) -0.0013(14) -0.0020(15) -0.0098(13) C23 0.059(2) 0.0350(18) 0.024(2) -0.0046(14) -0.0022(17) -0.0061(15) C24 0.062(2) 0.0363(18) 0.0242(19) -0.0020(14) -0.0048(17) -0.0068(16) C25 0.044(2) 0.0349(18) 0.029(2) -0.0020(15) -0.0069(16) -0.0091(14) C26 0.0303(18) 0.0342(18) 0.036(2) 0.0004(15) -0.0021(16) -0.0105(13) C27 0.0383(19) 0.0311(16) 0.0279(19) -0.0049(13) -0.0117(16) -0.0060(14) C28 0.053(2) 0.0410(18) 0.033(2) -0.0013(15) -0.0117(18) -0.0207(16) C29 0.059(2) 0.049(2) 0.025(2) -0.0039(15) -0.0054(17) -0.0164(17) C30 0.045(2) 0.0331(16) 0.029(2) -0.0094(14) -0.0138(17) -0.0019(14) C31 0.058(2) 0.0411(18) 0.034(2) -0.0065(16) -0.0080(18) -0.0213(16) C32 0.050(2) 0.0466(19) 0.027(2) -0.0038(15) -0.0054(17) -0.0170(16) C33 0.041(2) 0.0295(17) 0.031(2) -0.0024(14) -0.0177(17) -0.0008(14) C34 0.055(2) 0.0386(19) 0.031(2) -0.0079(16) -0.0118(18) -0.0036(16) N1 0.0428(17) 0.0383(15) 0.0289(17) -0.0060(12) -0.0042(13) -0.0112(12) N2 0.070(2) 0.0633(19) 0.047(2) -0.0035(16) -0.0042(18) -0.0384(17) N3 0.0431(17) 0.0428(15) 0.0312(17) -0.0031(12) -0.0023(14) -0.0132(13) N4 0.119(4) 0.120(3) 0.032(2) 0.014(2) 0.001(2) -0.076(3) N5 0.109(3) 0.097(3) 0.054(3) 0.014(2) -0.015(2) -0.072(2) N6 0.0453(17) 0.0379(14) 0.0275(17) 0.0002(12) -0.0099(13) -0.0147(12) O1 0.0693(17) 0.0399(12) 0.0280(14) -0.0089(10) -0.0052(13) -0.0189(11) O2 0.0535(15) 0.0340(11) 0.0409(15) -0.0039(10) -0.0239(12) -0.0152(10) O1W 0.214(6) 0.143(4) 0.163(5) 0.012(3) -0.013(4) -0.039(4) O3 0.088(2) 0.0507(15) 0.0409(16) -0.0166(12) -0.0090(14) -0.0275(14) O4 0.116(2) 0.0446(14) 0.0276(16) -0.0091(11) -0.0171(15) -0.0210(15) O5 0.0656(16) 0.0318(11) 0.0287(14) -0.0053(10) -0.0124(12) -0.0023(10) O6 0.0868(19) 0.0346(12) 0.0279(15) -0.0014(10) -0.0183(13) -0.0083(11) O7 0.0594(16) 0.0425(13) 0.0369(16) 0.0041(11) -0.0128(13) -0.0094(11) O8 0.0619(16) 0.0304(11) 0.0359(14) -0.0006(10) -0.0113(12) -0.0057(10) O9 0.0443(14) 0.0371(11) 0.0353(14) -0.0052(10) -0.0161(11) -0.0137(10) O10 0.0557(15) 0.0421(12) 0.0244(14) -0.0104(10) -0.0019(12) -0.0185(11) _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 Zn1 O8 1.929(2) . ? Zn1 O9 1.956(2) 1_465 ? Zn1 O1 1.991(2) 1_465 ? Zn1 N6 2.002(3) 1_564 ? Zn2 O5 1.934(2) . ? Zn2 O10 1.9534(19) . ? Zn2 O2 1.961(2) . ? Zn2 N1 1.989(3) . ? C1 N3 1.310(4) . ? C1 N1 1.328(4) . ? C1 H1 0.9300 . ? C2 N2 1.299(5) . ? C2 N1 1.355(4) . ? C2 H2 0.9300 . ? C3 N3 1.467(4) . ? C3 C4 1.502(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.501(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.524(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7' 1.375(12) . ? C6 C7 1.410(10) . ? C7 C7' 1.433(17) . ? C7 C8 1.619(10) . ? C7' C8 1.678(14) . ? C8 C9 1.481(9) . ? C9 C10 1.450(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.781(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.259(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N4 1.774(9) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N4 1.304(5) . ? C13 N6 1.307(4) . ? C13 H13 0.9300 . ? C14 N5 1.280(5) . ? C14 N6 1.351(4) . ? C14 H14 0.9300 . ? C15 C17 1.375(4) 2_656 ? C15 C16 1.385(4) . ? C15 H20 0.9300 . ? C16 C17 1.389(4) . ? C16 H19 0.9300 . ? C17 C15 1.375(4) 2_656 ? C17 C18 1.501(4) . ? C18 O10 1.256(4) . ? C18 O9 1.267(3) . ? C19 C20 1.381(4) . ? C19 C24 1.389(4) . ? C19 C25 1.494(4) . ? C20 C21 1.379(4) . ? C20 H6 0.9300 . ? C21 C22 1.396(4) . ? C21 H7 0.9300 . ? C22 C23 1.379(4) . ? C22 C26 1.502(4) . ? C23 C24 1.377(4) . ? C23 H3 0.9300 . ? C24 H4 0.9300 . ? C25 O6 1.232(4) . ? C25 O5 1.283(3) . ? C26 O7 1.230(4) . ? C26 O8 1.286(4) . ? C27 C28 1.376(4) . ? C27 C32 1.388(4) . ? C27 C33 1.497(4) . ? C28 C29 1.391(4) . ? C28 H28 0.9300 . ? C29 C30 1.376(4) . ? C29 H29 0.9300 . ? C30 C31 1.378(5) . ? C30 C34 1.496(4) . ? C31 C32 1.380(4) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 O1 1.255(4) . ? C33 O2 1.264(4) . ? C34 O3 1.202(4) . ? C34 O4 1.315(4) . ? N2 N3 1.365(4) . ? N4 N5 1.346(5) . ? N6 Zn1 2.002(3) 1_546 ? O1 Zn1 1.991(2) 1_645 ? O4 H4WA 0.86(2) . ? O9 Zn1 1.956(2) 1_645 ? 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 O8 Zn1 O9 118.82(9) . 1_465 ? O8 Zn1 O1 101.45(10) . 1_465 ? O9 Zn1 O1 116.05(9) 1_465 1_465 ? O8 Zn1 N6 118.90(10) . 1_564 ? O9 Zn1 N6 102.87(10) 1_465 1_564 ? O1 Zn1 N6 97.27(10) 1_465 1_564 ? O5 Zn2 O10 105.44(9) . . ? O5 Zn2 O2 112.37(9) . . ? O10 Zn2 O2 113.75(9) . . ? O5 Zn2 N1 115.81(10) . . ? O10 Zn2 N1 107.02(10) . . ? O2 Zn2 N1 102.62(11) . . ? N3 C1 N1 110.6(3) . . ? N3 C1 H1 124.7 . . ? N1 C1 H1 124.7 . . ? N2 C2 N1 114.7(3) . . ? N2 C2 H2 122.7 . . ? N1 C2 H2 122.7 . . ? N3 C3 C4 111.1(3) . . ? N3 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? N3 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 113.3(4) . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C6 113.3(4) . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C7' C6 C7 61.9(8) . . ? C7' C6 C5 122.2(7) . . ? C7 C6 C5 117.2(6) . . ? C6 C7 C7' 57.8(6) . . ? C6 C7 C8 114.4(7) . . ? C7' C7 C8 66.4(6) . . ? C6 C7' C7 60.3(7) . . ? C6 C7' C8 112.8(10) . . ? C7 C7' C8 62.1(8) . . ? C9 C8 C7 125.5(6) . . ? C9 C8 C7' 81.4(6) . . ? C7 C8 C7' 51.5(6) . . ? C10 C9 C8 114.7(6) . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? C8 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C9 C10 C11 106.0(7) . . ? C9 C10 H10A 110.5 . . ? C11 C10 H10A 110.5 . . ? C9 C10 H10B 110.5 . . ? C11 C10 H10B 110.5 . . ? H10A C10 H10B 108.7 . . ? C12 C11 C10 90.8(6) . . ? C12 C11 H11A 113.5 . . ? C10 C11 H11A 113.5 . . ? C12 C11 H11B 113.5 . . ? C10 C11 H11B 113.5 . . ? H11A C11 H11B 110.8 . . ? C11 C12 N4 91.7(6) . . ? C11 C12 H12A 113.3 . . ? N4 C12 H12A 113.3 . . ? C11 C12 H12B 113.3 . . ? N4 C12 H12B 113.3 . . ? H12A C12 H12B 110.7 . . ? N4 C13 N6 109.4(3) . . ? N4 C13 H13 125.3 . . ? N6 C13 H13 125.3 . . ? N5 C14 N6 115.1(3) . . ? N5 C14 H14 122.4 . . ? N6 C14 H14 122.4 . . ? C17 C15 C16 120.4(3) 2_656 . ? C17 C15 H20 119.8 2_656 . ? C16 C15 H20 119.8 . . ? C15 C16 C17 120.2(3) . . ? C15 C16 H19 119.9 . . ? C17 C16 H19 119.9 . . ? C15 C17 C16 119.4(3) 2_656 . ? C15 C17 C18 121.0(3) 2_656 . ? C16 C17 C18 119.6(3) . . ? O10 C18 O9 124.8(3) . . ? O10 C18 C17 117.6(3) . . ? O9 C18 C17 117.6(3) . . ? C20 C19 C24 119.1(3) . . ? C20 C19 C25 120.6(3) . . ? C24 C19 C25 120.3(3) . . ? C21 C20 C19 120.9(3) . . ? C21 C20 H6 119.5 . . ? C19 C20 H6 119.5 . . ? C20 C21 C22 120.1(3) . . ? C20 C21 H7 120.0 . . ? C22 C21 H7 120.0 . . ? C23 C22 C21 118.5(3) . . ? C23 C22 C26 121.3(3) . . ? C21 C22 C26 120.1(3) . . ? C24 C23 C22 121.5(3) . . ? C24 C23 H3 119.3 . . ? C22 C23 H3 119.3 . . ? C23 C24 C19 119.9(3) . . ? C23 C24 H4 120.1 . . ? C19 C24 H4 120.1 . . ? O6 C25 O5 122.4(3) . . ? O6 C25 C19 122.2(3) . . ? O5 C25 C19 115.4(3) . . ? O7 C26 O8 123.6(3) . . ? O7 C26 C22 121.0(3) . . ? O8 C26 C22 115.4(3) . . ? C28 C27 C32 119.6(3) . . ? C28 C27 C33 119.8(3) . . ? C32 C27 C33 120.6(3) . . ? C27 C28 C29 120.2(3) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? C30 C29 C28 119.8(3) . . ? C30 C29 H29 120.1 . . ? C28 C29 H29 120.1 . . ? C29 C30 C31 119.9(3) . . ? C29 C30 C34 121.2(3) . . ? C31 C30 C34 118.9(3) . . ? C30 C31 C32 120.4(3) . . ? C30 C31 H31 119.8 . . ? C32 C31 H31 119.8 . . ? C31 C32 C27 119.9(3) . . ? C31 C32 H32 120.1 . . ? C27 C32 H32 120.1 . . ? O1 C33 O2 124.3(3) . . ? O1 C33 C27 118.0(3) . . ? O2 C33 C27 117.7(3) . . ? O3 C34 O4 124.1(3) . . ? O3 C34 C30 123.0(3) . . ? O4 C34 C30 112.9(3) . . ? C1 N1 C2 102.4(3) . . ? C1 N1 Zn2 122.2(2) . . ? C2 N1 Zn2 134.0(2) . . ? C2 N2 N3 102.8(3) . . ? C1 N3 N2 109.6(3) . . ? C1 N3 C3 127.6(3) . . ? N2 N3 C3 122.7(3) . . ? C13 N4 N5 111.0(3) . . ? C13 N4 C12 130.0(4) . . ? N5 N4 C12 116.3(3) . . ? C14 N5 N4 101.8(3) . . ? C13 N6 C14 102.7(3) . . ? C13 N6 Zn1 130.3(2) . 1_546 ? C14 N6 Zn1 127.0(2) . 1_546 ? C33 O1 Zn1 117.08(19) . 1_645 ? C33 O2 Zn2 127.9(2) . . ? C34 O4 H4WA 106(2) . . ? C25 O5 Zn2 115.3(2) . . ? C26 O8 Zn1 112.4(2) . . ? C18 O9 Zn1 134.2(2) . 1_645 ? C18 O10 Zn2 120.06(18) . . ? 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 N3 C3 C4 C5 176.0(3) . . . . ? C3 C4 C5 C6 -171.8(4) . . . . ? C4 C5 C6 C7' 164.1(10) . . . . ? C4 C5 C6 C7 91.7(7) . . . . ? C5 C6 C7 C7' 113.9(9) . . . . ? C7' C6 C7 C8 -36.5(8) . . . . ? C5 C6 C7 C8 77.4(8) . . . . ? C5 C6 C7' C7 -106.0(9) . . . . ? C7 C6 C7' C8 34.5(8) . . . . ? C5 C6 C7' C8 -71.4(13) . . . . ? C8 C7 C7' C6 143.7(8) . . . . ? C6 C7 C7' C8 -143.7(8) . . . . ? C6 C7 C8 C9 69.8(10) . . . . ? C7' C7 C8 C9 36.4(9) . . . . ? C6 C7 C8 C7' 33.3(7) . . . . ? C6 C7' C8 C9 175.4(11) . . . . ? C7 C7' C8 C9 -150.7(8) . . . . ? C6 C7' C8 C7 -33.8(8) . . . . ? C7 C8 C9 C10 177.1(6) . . . . ? C7' C8 C9 C10 -154.8(7) . . . . ? C8 C9 C10 C11 172.7(5) . . . . ? C9 C10 C11 C12 -171.2(6) . . . . ? C10 C11 C12 N4 173.4(4) . . . . ? C17 C15 C16 C17 0.4(6) 2_656 . . . ? C15 C16 C17 C15 -0.4(5) . . . 2_656 ? C15 C16 C17 C18 179.6(3) . . . . ? C15 C17 C18 O10 -176.4(3) 2_656 . . . ? C16 C17 C18 O10 3.6(4) . . . . ? C15 C17 C18 O9 5.2(4) 2_656 . . . ? C16 C17 C18 O9 -174.8(3) . . . . ? C24 C19 C20 C21 -0.7(5) . . . . ? C25 C19 C20 C21 178.0(3) . . . . ? C19 C20 C21 C22 -0.7(5) . . . . ? C20 C21 C22 C23 2.4(5) . . . . ? C20 C21 C22 C26 -175.6(3) . . . . ? C21 C22 C23 C24 -2.6(5) . . . . ? C26 C22 C23 C24 175.3(3) . . . . ? C22 C23 C24 C19 1.2(5) . . . . ? C20 C19 C24 C23 0.5(5) . . . . ? C25 C19 C24 C23 -178.2(3) . . . . ? C20 C19 C25 O6 171.0(3) . . . . ? C24 C19 C25 O6 -10.3(5) . . . . ? C20 C19 C25 O5 -10.3(5) . . . . ? C24 C19 C25 O5 168.5(3) . . . . ? C23 C22 C26 O7 -162.8(3) . . . . ? C21 C22 C26 O7 15.1(5) . . . . ? C23 C22 C26 O8 17.3(4) . . . . ? C21 C22 C26 O8 -164.8(3) . . . . ? C32 C27 C28 C29 0.3(5) . . . . ? C33 C27 C28 C29 -178.6(3) . . . . ? C27 C28 C29 C30 2.4(5) . . . . ? C28 C29 C30 C31 -3.2(5) . . . . ? C28 C29 C30 C34 176.9(3) . . . . ? C29 C30 C31 C32 1.3(5) . . . . ? C34 C30 C31 C32 -178.8(3) . . . . ? C30 C31 C32 C27 1.3(5) . . . . ? C28 C27 C32 C31 -2.2(5) . . . . ? C33 C27 C32 C31 176.8(3) . . . . ? C28 C27 C33 O1 -168.5(3) . . . . ? C32 C27 C33 O1 12.6(4) . . . . ? C28 C27 C33 O2 10.8(4) . . . . ? C32 C27 C33 O2 -168.2(3) . . . . ? C29 C30 C34 O3 -165.7(3) . . . . ? C31 C30 C34 O3 14.5(5) . . . . ? C29 C30 C34 O4 13.4(5) . . . . ? C31 C30 C34 O4 -166.4(3) . . . . ? N3 C1 N1 C2 1.3(4) . . . . ? N3 C1 N1 Zn2 -167.0(2) . . . . ? N2 C2 N1 C1 -1.2(4) . . . . ? N2 C2 N1 Zn2 165.0(3) . . . . ? O5 Zn2 N1 C1 -75.2(3) . . . . ? O10 Zn2 N1 C1 167.6(2) . . . . ? O2 Zn2 N1 C1 47.6(3) . . . . ? O5 Zn2 N1 C2 120.8(3) . . . . ? O10 Zn2 N1 C2 3.6(3) . . . . ? O2 Zn2 N1 C2 -116.4(3) . . . . ? N1 C2 N2 N3 0.6(4) . . . . ? N1 C1 N3 N2 -1.1(4) . . . . ? N1 C1 N3 C3 174.3(3) . . . . ? C2 N2 N3 C1 0.3(4) . . . . ? C2 N2 N3 C3 -175.3(3) . . . . ? C4 C3 N3 C1 -69.5(4) . . . . ? C4 C3 N3 N2 105.3(4) . . . . ? N6 C13 N4 N5 1.6(6) . . . . ? N6 C13 N4 C12 -158.8(4) . . . . ? C11 C12 N4 C13 -77.3(7) . . . . ? C11 C12 N4 N5 123.2(5) . . . . ? N6 C14 N5 N4 0.6(5) . . . . ? C13 N4 N5 C14 -1.3(5) . . . . ? C12 N4 N5 C14 162.0(4) . . . . ? N4 C13 N6 C14 -1.1(5) . . . . ? N4 C13 N6 Zn1 176.6(3) . . . 1_546 ? N5 C14 N6 C13 0.3(5) . . . . ? N5 C14 N6 Zn1 -177.6(3) . . . 1_546 ? O2 C33 O1 Zn1 -15.9(4) . . . 1_645 ? C27 C33 O1 Zn1 163.3(2) . . . 1_645 ? O1 C33 O2 Zn2 -66.7(4) . . . . ? C27 C33 O2 Zn2 114.1(3) . . . . ? O5 Zn2 O2 C33 -11.7(3) . . . . ? O10 Zn2 O2 C33 108.0(3) . . . . ? N1 Zn2 O2 C33 -136.8(3) . . . . ? O6 C25 O5 Zn2 2.7(4) . . . . ? C19 C25 O5 Zn2 -176.0(2) . . . . ? O10 Zn2 O5 C25 172.9(2) . . . . ? O2 Zn2 O5 C25 -62.7(2) . . . . ? N1 Zn2 O5 C25 54.8(2) . . . . ? O7 C26 O8 Zn1 0.7(4) . . . . ? C22 C26 O8 Zn1 -179.4(2) . . . . ? O9 Zn1 O8 C26 52.0(2) 1_465 . . . ? O1 Zn1 O8 C26 -179.5(2) 1_465 . . . ? N6 Zn1 O8 C26 -74.5(2) 1_564 . . . ? O10 C18 O9 Zn1 56.7(4) . . . 1_645 ? C17 C18 O9 Zn1 -125.1(3) . . . 1_645 ? O9 C18 O10 Zn2 16.9(4) . . . . ? C17 C18 O10 Zn2 -161.4(2) . . . . ? O5 Zn2 O10 C18 55.2(3) . . . . ? O2 Zn2 O10 C18 -68.4(3) . . . . ? N1 Zn2 O10 C18 179.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.575 _refine_diff_density_min -0.565 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 961127' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_comp3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H30 N6 O6 Zn' _chemical_formula_weight 539.89 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'p -1' _symmetry_space_group_name_hall '-p 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0880(4) _cell_length_b 10.1850(4) _cell_length_c 15.0410(7) _cell_angle_alpha 109.498(4) _cell_angle_beta 92.338(4) _cell_angle_gamma 115.87(9) _cell_volume 1278.72(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5783 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 29.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 1.008 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.756 _exptl_absorpt_correction_T_max 0.789 _exptl_absorpt_process_details ? _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9247 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 29.22 _reflns_number_total 5783 _reflns_number_gt 4108 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 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^)+(0.0725P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5783 _refine_ls_number_parameters 325 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1082 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.940 _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 Zn1 Zn 0.69639(3) 0.08857(3) 0.38240(2) 0.03791(12) Uani 1 1 d . . . C1 C 0.8789(3) 0.1933(3) 0.2429(2) 0.0507(7) Uani 1 1 d . . . H1 H 0.8882 0.2943 0.2692 0.061 Uiso 1 1 calc R . . C2 C 0.8261(4) -0.0411(4) 0.2139(2) 0.0633(8) Uani 1 1 d . . . H2 H 0.7868 -0.1394 0.2184 0.076 Uiso 1 1 calc R . . C3 C 1.0330(6) 0.2327(6) 0.1189(3) 0.1001(14) Uani 1 1 d . . . H3A H 1.0482 0.3403 0.1460 0.120 Uiso 1 1 calc R . . H3B H 0.9814 0.1858 0.0515 0.120 Uiso 1 1 calc R . . C4 C 1.1805(5) 0.2382(6) 0.1235(3) 0.1024(15) Uani 1 1 d . . . H4A H 1.1683 0.1345 0.0848 0.123 Uiso 1 1 calc R . . H4B H 1.2257 0.2668 0.1898 0.123 Uiso 1 1 calc R . . C5 C 1.2854(7) 0.3622(7) 0.0851(5) 0.157(3) Uani 1 1 d . . . H5A H 1.2381 0.3336 0.0193 0.188 Uiso 1 1 calc R . . H5B H 1.2964 0.4652 0.1242 0.188 Uiso 1 1 calc R . . C6 C 1.4247(9) 0.3727(11) 0.0867(6) 0.232(5) Uani 1 1 d . . . H6A H 1.4167 0.2722 0.0453 0.278 Uiso 1 1 calc R . . H6B H 1.4738 0.4004 0.1520 0.278 Uiso 1 1 calc R . . C7 C 1.5217(11) 0.5109(10) 0.0477(5) 0.302(8) Uani 1 1 d . . . H7A H 1.5226 0.6075 0.0894 0.363 Uiso 1 1 calc R . . H7B H 1.6252 0.5299 0.0574 0.363 Uiso 1 1 calc R . . C8 C 0.7519(3) 0.1212(4) 0.5857(2) 0.0543(7) Uani 1 1 d . . . H8 H 0.6669 0.0238 0.5710 0.065 Uiso 1 1 calc R . . C9 C 0.9239(3) 0.3250(3) 0.5781(2) 0.0567(7) Uani 1 1 d . . . H9 H 0.9835 0.3981 0.5534 0.068 Uiso 1 1 calc R . . C10 C 0.8313(8) 0.1809(7) 0.7608(3) 0.127(2) Uani 1 1 d . . . H10A H 0.7810 0.0669 0.7422 0.152 Uiso 1 1 calc R . . H10B H 0.9327 0.2233 0.7968 0.152 Uiso 1 1 calc R . . C11 C 0.7604(9) 0.2387(14) 0.8163(6) 0.212(4) Uani 1 1 d . . . H11A H 0.6597 0.1988 0.7802 0.254 Uiso 1 1 calc R . . H11B H 0.8124 0.3531 0.8371 0.254 Uiso 1 1 calc R . . C12 C 0.7479(8) 0.1958(12) 0.9083(5) 0.205(4) Uani 1 1 d . . . H12A H 0.8163 0.1538 0.9139 0.245 Uiso 1 1 calc R . . H12B H 0.7802 0.2919 0.9654 0.245 Uiso 1 1 calc R . . C13 C 0.5953(7) 0.0799(8) 0.9056(3) 0.143(2) Uani 1 1 d . . . H13A H 0.5692 -0.0215 0.8547 0.172 Uiso 1 1 calc R . . H13B H 0.5245 0.1137 0.8897 0.172 Uiso 1 1 calc R . . C14 C 0.5786(5) 0.0586(8) 1.0017(3) 0.133(2) Uani 1 1 d . . . H14A H 0.6481 0.0231 1.0172 0.160 Uiso 1 1 calc R . . H14B H 0.6057 0.1601 1.0528 0.160 Uiso 1 1 calc R . . C15 C 0.5428(2) 0.3925(2) 0.37743(16) 0.0314(5) Uani 1 1 d . . . C16 C 0.6235(2) 0.5408(2) 0.37525(17) 0.0332(5) Uani 1 1 d . . . H16 H 0.7254 0.5805 0.3739 0.040 Uiso 1 1 calc R . . C17 C 0.5519(2) 0.6308(2) 0.37512(17) 0.0317(5) Uani 1 1 d . . . C18 C 0.4005(2) 0.5720(3) 0.37744(17) 0.0333(5) Uani 1 1 d . . . H18 H 0.3528 0.6319 0.3767 0.040 Uiso 1 1 calc R . . C19 C 0.3194(2) 0.4236(3) 0.38093(17) 0.0338(5) Uani 1 1 d . . . C20 C 0.3911(2) 0.3336(2) 0.38010(17) 0.0331(5) Uani 1 1 d . . . H20 H 0.3371 0.2336 0.3813 0.040 Uiso 1 1 calc R . . C21 C 0.6208(3) 0.2972(3) 0.37969(18) 0.0360(5) Uani 1 1 d . . . C22 C 0.6412(3) 0.7940(3) 0.37661(18) 0.0370(5) Uani 1 1 d . . . O1 O 0.53905(18) 0.15537(18) 0.37323(13) 0.0433(4) Uani 1 1 d . . . O2 O 0.75868(19) 0.3554(2) 0.38844(15) 0.0492(5) Uani 1 1 d . . . O1W O 0.0764(2) 0.1092(3) 0.42668(18) 0.0601(6) Uani 1 1 d D . . O3 O 0.78231(19) 0.85634(19) 0.39313(15) 0.0506(5) Uani 1 1 d . . . O4 O 0.56858(18) 0.86281(18) 0.36186(14) 0.0456(4) Uani 1 1 d . . . O5 O 0.17139(19) 0.3708(2) 0.38445(16) 0.0493(5) Uani 1 1 d D . . N1 N 0.8060(2) 0.0787(2) 0.27333(15) 0.0428(5) Uani 1 1 d . . . N2 N 0.9365(3) 0.1433(3) 0.16978(19) 0.0626(7) Uani 1 1 d . . . N3 N 0.9039(4) -0.0100(4) 0.1500(2) 0.0785(8) Uani 1 1 d . . . N4 N 0.8006(2) 0.1864(2) 0.52278(16) 0.0416(5) Uani 1 1 d . . . N5 N 0.9522(3) 0.3474(4) 0.6686(2) 0.0764(8) Uani 1 1 d . . . N6 N 0.8412(4) 0.2143(4) 0.6720(2) 0.0700(7) Uani 1 1 d . . . H1WA H -0.007(3) 0.039(4) 0.414(3) 0.105 Uiso 1 1 d D . . H1WB H 0.120(4) 0.128(5) 0.480(2) 0.105 Uiso 1 1 d D . . H5WA H 0.132(4) 0.285(4) 0.395(3) 0.105 Uiso 1 1 d 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 Zn1 0.03362(17) 0.02928(16) 0.0636(2) 0.02756(14) 0.01725(13) 0.01829(12) C1 0.0482(16) 0.0485(16) 0.0588(18) 0.0293(14) 0.0158(13) 0.0193(13) C2 0.076(2) 0.0456(17) 0.073(2) 0.0262(16) 0.0336(17) 0.0284(16) C3 0.123(4) 0.112(3) 0.093(3) 0.072(3) 0.068(3) 0.052(3) C4 0.089(3) 0.102(3) 0.067(2) 0.029(2) 0.032(2) 0.007(3) C5 0.136(5) 0.109(4) 0.163(5) 0.041(4) 0.101(4) 0.011(4) C6 0.162(7) 0.231(9) 0.174(7) 0.066(6) 0.094(6) -0.007(7) C7 0.276(11) 0.177(7) 0.201(9) 0.015(8) 0.167(10) -0.068(7) C8 0.0560(17) 0.0524(17) 0.071(2) 0.0361(16) 0.0267(16) 0.0295(15) C9 0.0480(16) 0.0478(17) 0.073(2) 0.0275(15) 0.0162(15) 0.0185(14) C10 0.209(6) 0.173(5) 0.069(3) 0.058(3) 0.045(3) 0.141(5) C11 0.206(7) 0.441(15) 0.169(6) 0.219(9) 0.122(6) 0.226(9) C12 0.132(5) 0.400(13) 0.127(5) 0.183(7) 0.059(4) 0.104(7) C13 0.132(5) 0.223(7) 0.072(3) 0.082(4) 0.026(3) 0.064(5) C14 0.105(4) 0.197(6) 0.082(3) 0.077(4) 0.020(3) 0.043(4) C15 0.0330(11) 0.0236(11) 0.0427(13) 0.0170(10) 0.0102(10) 0.0147(9) C16 0.0287(11) 0.0256(11) 0.0511(14) 0.0205(10) 0.0142(10) 0.0133(9) C17 0.0318(11) 0.0255(11) 0.0441(13) 0.0202(10) 0.0105(10) 0.0139(9) C18 0.0327(12) 0.0270(11) 0.0490(14) 0.0207(10) 0.0107(10) 0.0173(9) C19 0.0270(11) 0.0293(11) 0.0476(14) 0.0197(10) 0.0096(10) 0.0120(9) C20 0.0333(12) 0.0231(10) 0.0477(14) 0.0213(10) 0.0109(10) 0.0120(9) C21 0.0354(13) 0.0296(12) 0.0505(15) 0.0206(11) 0.0140(10) 0.0178(10) C22 0.0368(13) 0.0262(11) 0.0532(15) 0.0220(11) 0.0118(11) 0.0145(10) O1 0.0347(9) 0.0276(8) 0.0793(13) 0.0307(9) 0.0157(8) 0.0173(7) O2 0.0342(9) 0.0374(9) 0.0886(14) 0.0331(9) 0.0199(9) 0.0208(8) O1W 0.0342(10) 0.0571(13) 0.0941(16) 0.0521(13) 0.0154(10) 0.0094(9) O3 0.0342(10) 0.0333(9) 0.0919(14) 0.0377(10) 0.0146(9) 0.0127(8) O4 0.0391(9) 0.0284(8) 0.0793(13) 0.0320(9) 0.0112(9) 0.0166(7) O5 0.0289(9) 0.0422(10) 0.0893(14) 0.0391(10) 0.0193(9) 0.0171(8) N1 0.0403(11) 0.0353(11) 0.0552(13) 0.0222(10) 0.0156(10) 0.0162(9) N2 0.0708(17) 0.0602(16) 0.0604(16) 0.0337(14) 0.0269(13) 0.0258(14) N3 0.099(2) 0.0672(19) 0.0707(19) 0.0289(16) 0.0440(17) 0.0371(18) N4 0.0386(11) 0.0370(11) 0.0624(14) 0.0284(10) 0.0196(10) 0.0219(10) N5 0.0689(19) 0.079(2) 0.0676(19) 0.0225(16) 0.0033(14) 0.0292(17) N6 0.082(2) 0.085(2) 0.0625(18) 0.0398(16) 0.0246(15) 0.0477(18) _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 Zn1 O4 1.988(3) 1_545 ? Zn1 O1 1.9971(17) . ? Zn1 N4 2.014(2) . ? Zn1 N1 2.014(2) . ? Zn1 O2 2.4760(19) . ? Zn1 C21 2.563(2) . ? C1 N2 1.321(4) . ? C1 N1 1.322(3) . ? C1 H1 0.9300 . ? C2 N3 1.298(4) . ? C2 N1 1.354(4) . ? C2 H2 0.9300 . ? C3 N2 1.455(4) . ? C3 C4 1.462(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.555(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.361(11) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.637(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C7 1.397(18) 2_865 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N6 1.317(4) . ? C8 N4 1.322(3) . ? C8 H8 0.9300 . ? C9 N5 1.300(4) . ? C9 N4 1.354(4) . ? C9 H9 0.9300 . ? C10 C11 1.282(8) . ? C10 N6 1.481(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.578(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.464(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.538(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C14 1.497(10) 2_657 ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.382(3) . ? C15 C20 1.387(3) . ? C15 C21 1.500(3) . ? C16 C17 1.394(3) . ? C16 H16 0.9300 . ? C17 C18 1.382(3) . ? C17 C22 1.497(3) . ? C18 C19 1.390(3) . ? C18 H18 0.9300 . ? C19 O5 1.359(3) . ? C19 C20 1.391(3) . ? C20 H20 0.9300 . ? C21 O2 1.232(3) . ? C21 O1 1.279(3) . ? C22 O3 1.252(3) . ? C22 O4 1.271(3) . ? O1W H1WA 0.79(2) . ? O1W H1WB 0.81(2) . ? O4 Zn1 1.988(3) 1_565 ? O5 H5WA 0.86(3) . ? N2 N3 1.367(4) . ? N5 N6 1.349(4) . ? 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 O4 Zn1 O1 100.86(9) 1_545 . ? O4 Zn1 N4 102.05(10) 1_545 . ? O1 Zn1 N4 107.28(8) . . ? O4 Zn1 N1 104.11(9) 1_545 . ? O1 Zn1 N1 115.42(8) . . ? N4 Zn1 N1 123.60(9) . . ? O4 Zn1 O2 158.08(6) 1_545 . ? O1 Zn1 O2 57.61(10) . . ? N4 Zn1 O2 89.58(9) . . ? N1 Zn1 O2 84.04(9) . . ? O4 Zn1 C21 130.13(7) 1_545 . ? O1 Zn1 C21 29.37(8) . . ? N4 Zn1 C21 99.26(8) . . ? N1 Zn1 C21 100.44(9) . . ? O2 Zn1 C21 28.23(7) . . ? N2 C1 N1 110.0(3) . . ? N2 C1 H1 125.0 . . ? N1 C1 H1 125.0 . . ? N3 C2 N1 115.6(3) . . ? N3 C2 H2 122.2 . . ? N1 C2 H2 122.2 . . ? N2 C3 C4 114.1(4) . . ? N2 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? N2 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C3 C4 C5 109.9(5) . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4B 109.7 . . ? C5 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C6 C5 C4 113.0(7) . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C5 C6 C7 106.8(9) . . ? C5 C6 H6A 110.4 . . ? C7 C6 H6A 110.4 . . ? C5 C6 H6B 110.4 . . ? C7 C6 H6B 110.4 . . ? H6A C6 H6B 108.6 . . ? C7 C7 C6 120.0(8) 2_865 . ? C7 C7 H7A 107.3 2_865 . ? C6 C7 H7A 107.3 . . ? C7 C7 H7B 107.3 2_865 . ? C6 C7 H7B 107.3 . . ? H7A C7 H7B 106.9 . . ? N6 C8 N4 110.2(3) . . ? N6 C8 H8 124.9 . . ? N4 C8 H8 124.9 . . ? N5 C9 N4 114.4(3) . . ? N5 C9 H9 122.8 . . ? N4 C9 H9 122.8 . . ? C11 C10 N6 114.3(5) . . ? C11 C10 H10A 108.7 . . ? N6 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? N6 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 112.6(7) . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 113.5(5) . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C12 C13 C14 113.1(4) . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C14 C14 C13 112.5(5) 2_657 . ? C14 C14 H14A 109.1 2_657 . ? C13 C14 H14A 109.1 . . ? C14 C14 H14B 109.1 2_657 . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C20 120.1(2) . . ? C16 C15 C21 119.73(19) . . ? C20 C15 C21 120.10(19) . . ? C15 C16 C17 119.8(2) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C18 C17 C16 120.1(2) . . ? C18 C17 C22 120.2(2) . . ? C16 C17 C22 119.62(19) . . ? C17 C18 C19 120.3(2) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? O5 C19 C18 118.5(2) . . ? O5 C19 C20 122.0(2) . . ? C18 C19 C20 119.4(2) . . ? C15 C20 C19 120.3(2) . . ? C15 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? O2 C21 O1 121.9(2) . . ? O2 C21 C15 120.6(2) . . ? O1 C21 C15 117.50(19) . . ? O2 C21 Zn1 71.96(14) . . ? O1 C21 Zn1 49.98(10) . . ? C15 C21 Zn1 167.45(16) . . ? O3 C22 O4 123.4(2) . . ? O3 C22 C17 119.0(2) . . ? O4 C22 C17 117.6(2) . . ? C21 O1 Zn1 100.64(15) . . ? C21 O2 Zn1 79.80(16) . . ? H1WA O1W H1WB 110(3) . . ? C22 O4 Zn1 114.76(15) . 1_565 ? C19 O5 H5WA 113(3) . . ? C1 N1 C2 102.4(2) . . ? C1 N1 Zn1 127.15(19) . . ? C2 N1 Zn1 130.41(19) . . ? C1 N2 N3 110.1(2) . . ? C1 N2 C3 128.5(3) . . ? N3 N2 C3 121.1(3) . . ? C2 N3 N2 101.7(3) . . ? C8 N4 C9 102.6(2) . . ? C8 N4 Zn1 124.1(2) . . ? C9 N4 Zn1 133.26(19) . . ? C9 N5 N6 103.0(3) . . ? C8 N6 N5 109.8(3) . . ? C8 N6 C10 127.1(4) . . ? N5 N6 C10 123.0(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 N2 C3 C4 C5 -168.9(4) . . . . ? C3 C4 C5 C6 -179.5(6) . . . . ? C4 C5 C6 C7 -178.2(5) . . . . ? C5 C6 C7 C7 -65.4(17) . . . 2_865 ? N6 C10 C11 C12 178.2(6) . . . . ? C10 C11 C12 C13 -108.3(9) . . . . ? C11 C12 C13 C14 -170.9(7) . . . . ? C12 C13 C14 C14 179.2(8) . . . 2_657 ? C20 C15 C16 C17 -0.4(4) . . . . ? C21 C15 C16 C17 -178.7(2) . . . . ? C15 C16 C17 C18 0.2(4) . . . . ? C15 C16 C17 C22 177.7(2) . . . . ? C16 C17 C18 C19 0.7(4) . . . . ? C22 C17 C18 C19 -176.8(2) . . . . ? C17 C18 C19 O5 179.1(2) . . . . ? C17 C18 C19 C20 -1.3(4) . . . . ? C16 C15 C20 C19 -0.2(4) . . . . ? C21 C15 C20 C19 178.1(2) . . . . ? O5 C19 C20 C15 -179.4(2) . . . . ? C18 C19 C20 C15 1.1(4) . . . . ? C16 C15 C21 O2 6.6(4) . . . . ? C20 C15 C21 O2 -171.7(2) . . . . ? C16 C15 C21 O1 -174.1(2) . . . . ? C20 C15 C21 O1 7.6(3) . . . . ? C16 C15 C21 Zn1 -177.7(7) . . . . ? C20 C15 C21 Zn1 4.0(9) . . . . ? O4 Zn1 C21 O2 -174.16(14) 1_545 . . . ? O1 Zn1 C21 O2 -179.7(3) . . . . ? N4 Zn1 C21 O2 71.38(17) . . . . ? N1 Zn1 C21 O2 -55.50(16) . . . . ? O4 Zn1 C21 O1 5.55(19) 1_545 . . . ? N4 Zn1 C21 O1 -108.90(17) . . . . ? N1 Zn1 C21 O1 124.21(16) . . . . ? O2 Zn1 C21 O1 179.7(3) . . . . ? O4 Zn1 C21 C15 9.8(8) 1_545 . . . ? O1 Zn1 C21 C15 4.2(7) . . . . ? N4 Zn1 C21 C15 -104.7(8) . . . . ? N1 Zn1 C21 C15 128.4(8) . . . . ? O2 Zn1 C21 C15 -176.1(9) . . . . ? C18 C17 C22 O3 166.4(2) . . . . ? C16 C17 C22 O3 -11.1(4) . . . . ? C18 C17 C22 O4 -12.8(4) . . . . ? C16 C17 C22 O4 169.7(2) . . . . ? O2 C21 O1 Zn1 0.3(3) . . . . ? C15 C21 O1 Zn1 -178.97(17) . . . . ? O4 Zn1 O1 C21 -175.68(15) 1_545 . . . ? N4 Zn1 O1 C21 77.93(17) . . . . ? N1 Zn1 O1 C21 -64.21(17) . . . . ? O2 Zn1 O1 C21 -0.16(14) . . . . ? O1 C21 O2 Zn1 -0.3(2) . . . . ? C15 C21 O2 Zn1 179.0(2) . . . . ? O4 Zn1 O2 C21 12.0(3) 1_545 . . . ? O1 Zn1 O2 C21 0.16(15) . . . . ? N4 Zn1 O2 C21 -110.72(16) . . . . ? N1 Zn1 O2 C21 125.42(16) . . . . ? O3 C22 O4 Zn1 -7.0(3) . . . 1_565 ? C17 C22 O4 Zn1 172.23(16) . . . 1_565 ? N2 C1 N1 C2 0.6(3) . . . . ? N2 C1 N1 Zn1 -179.93(18) . . . . ? N3 C2 N1 C1 -0.3(4) . . . . ? N3 C2 N1 Zn1 -179.7(2) . . . . ? O4 Zn1 N1 C1 164.3(2) 1_545 . . . ? O1 Zn1 N1 C1 54.8(3) . . . . ? N4 Zn1 N1 C1 -80.5(3) . . . . ? O2 Zn1 N1 C1 5.0(2) . . . . ? C21 Zn1 N1 C1 28.1(2) . . . . ? O4 Zn1 N1 C2 -16.4(3) 1_545 . . . ? O1 Zn1 N1 C2 -126.0(3) . . . . ? N4 Zn1 N1 C2 98.7(3) . . . . ? O2 Zn1 N1 C2 -175.7(3) . . . . ? C21 Zn1 N1 C2 -152.7(3) . . . . ? N1 C1 N2 N3 -0.8(4) . . . . ? N1 C1 N2 C3 -175.5(3) . . . . ? C4 C3 N2 C1 119.7(4) . . . . ? C4 C3 N2 N3 -54.6(5) . . . . ? N1 C2 N3 N2 -0.2(4) . . . . ? C1 N2 N3 C2 0.6(4) . . . . ? C3 N2 N3 C2 175.8(3) . . . . ? N6 C8 N4 C9 -0.6(3) . . . . ? N6 C8 N4 Zn1 -178.53(18) . . . . ? N5 C9 N4 C8 -0.1(3) . . . . ? N5 C9 N4 Zn1 177.6(2) . . . . ? O4 Zn1 N4 C8 -19.3(2) 1_545 . . . ? O1 Zn1 N4 C8 86.3(2) . . . . ? N1 Zn1 N4 C8 -135.5(2) . . . . ? O2 Zn1 N4 C8 142.0(2) . . . . ? C21 Zn1 N4 C8 115.3(2) . . . . ? O4 Zn1 N4 C9 163.4(2) 1_545 . . . ? O1 Zn1 N4 C9 -91.0(2) . . . . ? N1 Zn1 N4 C9 47.3(3) . . . . ? O2 Zn1 N4 C9 -35.3(2) . . . . ? C21 Zn1 N4 C9 -61.9(2) . . . . ? N4 C9 N5 N6 0.7(4) . . . . ? N4 C8 N6 N5 1.0(4) . . . . ? N4 C8 N6 C10 -176.2(3) . . . . ? C9 N5 N6 C8 -1.0(4) . . . . ? C9 N5 N6 C10 176.4(3) . . . . ? C11 C10 N6 C8 -96.2(8) . . . . ? C11 C10 N6 N5 86.9(8) . . . . ? 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 O1W H1WB O3 0.81(2) 2.04(2) 2.848(3) 172(4) 2_666 O1W H1WA O3 0.79(2) 2.04(3) 2.834(5) 174(4) 1_445 O5 H5WA O1W 0.86(3) 1.86(3) 2.715(3) 172(4) . _diffrn_measured_fraction_theta_max 0.834 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.662 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 961128' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_comp4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H32 Cd0 N6 O8 Zn' _chemical_formula_weight 585.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd 0.1185 4.6533 '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' _symmetry_space_group_name_hall '-p 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.142(2) _cell_length_b 11.524(2) _cell_length_c 11.819(2) _cell_angle_alpha 85.816(15) _cell_angle_beta 88.121(17) _cell_angle_gamma 77.469(17) _cell_volume 1344.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3695 _cell_measurement_theta_min 3.8 _cell_measurement_theta_max 58.9 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 1.762 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.731 _exptl_absorpt_correction_T_max 0.771 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6318 _diffrn_reflns_av_R_equivalents 0.1419 _diffrn_reflns_av_sigmaI/netI 0.1159 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 58.93 _reflns_number_total 3695 _reflns_number_gt 2105 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 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^)+(0.0900P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3695 _refine_ls_number_parameters 358 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1288 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.1969 _refine_ls_wR_factor_gt 0.1671 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.002 _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 Zn1 Zn 0.43077(8) 0.12611(7) 0.34066(8) 0.0434(4) Uani 1 1 d . . . C1 C 0.2786(7) 0.3076(6) 0.1656(6) 0.0516(19) Uani 1 1 d . . . H1 H 0.1982 0.2821 0.1786 0.062 Uiso 1 1 calc R . . C2 C 0.4795(8) 0.3216(7) 0.1655(6) 0.058(2) Uani 1 1 d . . . H2 H 0.5712 0.3046 0.1810 0.069 Uiso 1 1 calc R . . C3 C 0.1859(8) 0.4967(6) 0.0475(7) 0.067(2) Uani 1 1 d . . . H21A H 0.0984 0.4904 0.0798 0.080 Uiso 1 1 calc R . . H21B H 0.1859 0.4823 -0.0323 0.080 Uiso 1 1 calc R . . C4 C 0.2058(9) 0.6203(6) 0.0587(8) 0.071(2) Uani 1 1 d . . . H22A H 0.2871 0.6301 0.0169 0.085 Uiso 1 1 calc R . . H22B H 0.2191 0.6306 0.1379 0.085 Uiso 1 1 calc R . . C5 C 0.0883(9) 0.7157(7) 0.0153(8) 0.071(2) Uani 1 1 d . . . H23A H 0.0726 0.7033 -0.0630 0.085 Uiso 1 1 calc R . . H23B H 0.0078 0.7080 0.0592 0.085 Uiso 1 1 calc R . . C6 C 0.1104(9) 0.8391(7) 0.0218(8) 0.080(3) Uani 1 1 d . . . H15A H 0.1828 0.8500 -0.0308 0.096 Uiso 1 1 calc R . . H15B H 0.1400 0.8468 0.0976 0.096 Uiso 1 1 calc R . . C7 C -0.0122(9) 0.9376(6) -0.0044(8) 0.075(3) Uani 1 1 d . . . H16A H -0.0852 0.9265 0.0476 0.091 Uiso 1 1 calc R . . H16B H -0.0412 0.9310 -0.0806 0.091 Uiso 1 1 calc R . . C8 C 0.4878(7) 0.2254(6) 0.5573(6) 0.0467(18) Uani 1 1 d . . . H8 H 0.5492 0.1563 0.5811 0.056 Uiso 1 1 calc R . . C9 C 0.3428(8) 0.3529(6) 0.4680(7) 0.059(2) Uani 1 1 d . . . H9 H 0.2807 0.3879 0.4127 0.071 Uiso 1 1 calc R . . C10 C 0.5166(8) 0.3521(7) 0.7161(6) 0.059(2) Uani 1 1 d . . . H27A H 0.5432 0.4282 0.7061 0.071 Uiso 1 1 calc R . . H27B H 0.5963 0.2915 0.7359 0.071 Uiso 1 1 calc R . . C11 C 0.4136(9) 0.3564(7) 0.8116(6) 0.065(2) Uani 1 1 d . . . H28A H 0.4475 0.3875 0.8762 0.077 Uiso 1 1 calc R . . H28B H 0.3315 0.4120 0.7879 0.077 Uiso 1 1 calc R . . C12 C 0.3784(8) 0.2390(7) 0.8497(7) 0.063(2) Uani 1 1 d . . . H29A H 0.3515 0.2046 0.7839 0.076 Uiso 1 1 calc R . . H29B H 0.3010 0.2540 0.9011 0.076 Uiso 1 1 calc R . . C13 C 0.4901(10) 0.1487(8) 0.9079(7) 0.073(2) Uani 1 1 d . . . H30A H 0.5305 0.1878 0.9634 0.087 Uiso 1 1 calc R . . H30B H 0.5595 0.1200 0.8521 0.087 Uiso 1 1 calc R . . C14 C 0.4440(9) 0.0426(7) 0.9673(7) 0.070(2) Uani 1 1 d . . . H31A H 0.4100 -0.0004 0.9112 0.084 Uiso 1 1 calc R . . H31B H 0.3702 0.0712 1.0194 0.084 Uiso 1 1 calc R . . C15 C 0.0791(6) -0.0041(6) 0.3531(5) 0.0394(16) Uani 1 1 d . . . C16 C 0.1135(6) -0.1267(6) 0.3599(5) 0.0407(16) Uani 1 1 d . . . H3 H 0.2035 -0.1666 0.3634 0.049 Uiso 1 1 calc R . . C17 C 0.0102(6) -0.1902(6) 0.3613(6) 0.0413(16) Uani 1 1 d . . . C18 C -0.1238(6) -0.1313(6) 0.3584(6) 0.0421(16) Uani 1 1 d . . . H5 H -0.1916 -0.1743 0.3617 0.050 Uiso 1 1 calc R . . C19 C -0.1569(6) -0.0073(5) 0.3505(5) 0.0367(15) Uani 1 1 d . . . C20 C -0.0553(6) 0.0558(6) 0.3477(5) 0.0435(17) Uani 1 1 d . . . H7 H -0.0769 0.1386 0.3421 0.052 Uiso 1 1 calc R . . C21 C 0.1895(7) 0.0683(6) 0.3496(6) 0.0422(17) Uani 1 1 d . . . C22 C 0.0513(8) -0.3235(7) 0.3606(7) 0.063(2) Uani 1 1 d . . . C23 C -0.3025(6) 0.0613(6) 0.3438(6) 0.0407(16) Uani 1 1 d . . . N1 N 0.3973(5) 0.2515(5) 0.2059(5) 0.0451(14) Uani 1 1 d . . . N2 N 0.4219(7) 0.4158(6) 0.1028(5) 0.0624(18) Uani 1 1 d . . . N3 N 0.2912(6) 0.4048(5) 0.1045(5) 0.0527(16) Uani 1 1 d . . . N4 N 0.4127(5) 0.2373(5) 0.4670(5) 0.0474(15) Uani 1 1 d . . . N5 N 0.4635(6) 0.3258(5) 0.6095(5) 0.0498(15) Uani 1 1 d . . . N6 N 0.3694(7) 0.4099(5) 0.5520(6) 0.0641(18) Uani 1 1 d . . . O1 O 0.3109(4) 0.0124(4) 0.3453(4) 0.0493(12) Uani 1 1 d . . . O2 O 0.1556(5) 0.1776(4) 0.3496(4) 0.0578(14) Uani 1 1 d . . . O1W O -0.0077(9) -0.5965(5) 0.3036(8) 0.114(3) Uani 1 1 d D . . O3 O -0.3254(5) 0.1702(5) 0.3306(6) 0.0769(18) Uani 1 1 d . . . O2W O -0.2579(8) 0.3825(6) 0.3309(8) 0.110(2) Uani 1 1 d D . . O4 O -0.3971(4) 0.0057(4) 0.3494(4) 0.0499(12) Uani 1 1 d . . . O5 O -0.0509(6) -0.3754(5) 0.3567(8) 0.113(3) Uani 1 1 d D . . O6 O 0.1672(6) -0.3783(5) 0.3619(7) 0.098(2) Uani 1 1 d . . . H1WA H 0.028(12) -0.666(5) 0.283(8) 0.148 Uiso 1 1 d D . . H1WB H -0.011(14) -0.610(10) 0.377(3) 0.148 Uiso 1 1 d D . . H2WA H -0.191(9) 0.328(8) 0.310(8) 0.148 Uiso 1 1 d D . . H2WB H -0.270(12) 0.356(10) 0.402(4) 0.148 Uiso 1 1 d D . . H5WA H -0.026(12) -0.449(4) 0.347(10) 0.148 Uiso 1 1 d 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 Zn1 0.0312(6) 0.0370(6) 0.0631(6) 0.0029(4) -0.0044(4) -0.0115(4) C1 0.048(5) 0.053(5) 0.057(5) 0.009(4) -0.005(4) -0.021(4) C2 0.043(5) 0.068(5) 0.062(5) 0.014(4) 0.003(4) -0.020(4) C3 0.066(5) 0.052(5) 0.082(6) 0.019(4) -0.034(5) -0.014(4) C4 0.070(6) 0.042(5) 0.093(6) 0.009(4) -0.010(5) 0.000(4) C5 0.076(6) 0.047(5) 0.086(6) 0.006(4) -0.018(5) -0.004(4) C6 0.070(6) 0.054(5) 0.107(7) 0.013(5) -0.019(5) 0.002(4) C7 0.071(6) 0.054(5) 0.093(7) 0.007(5) -0.007(5) 0.003(5) C8 0.030(4) 0.051(5) 0.060(5) 0.001(4) 0.002(3) -0.012(3) C9 0.057(5) 0.046(5) 0.065(5) 0.002(4) -0.018(4) 0.006(4) C10 0.061(5) 0.065(5) 0.059(5) -0.014(4) -0.003(4) -0.024(4) C11 0.078(6) 0.064(5) 0.055(5) -0.002(4) -0.005(4) -0.024(5) C12 0.065(6) 0.072(6) 0.055(5) -0.002(4) 0.000(4) -0.021(5) C13 0.089(7) 0.071(6) 0.061(5) -0.008(4) 0.005(5) -0.024(5) C14 0.083(6) 0.070(6) 0.064(6) 0.000(4) -0.008(4) -0.030(5) C15 0.025(3) 0.045(4) 0.049(4) 0.008(3) -0.002(3) -0.014(3) C16 0.031(4) 0.038(4) 0.055(4) 0.005(3) 0.004(3) -0.014(3) C17 0.029(4) 0.033(4) 0.061(4) -0.002(3) 0.008(3) -0.005(3) C18 0.028(4) 0.044(4) 0.057(4) -0.001(3) 0.003(3) -0.016(3) C19 0.023(3) 0.035(4) 0.056(4) 0.003(3) -0.002(3) -0.016(3) C20 0.037(4) 0.042(4) 0.051(4) 0.007(3) -0.008(3) -0.010(3) C21 0.034(4) 0.047(5) 0.050(4) 0.014(3) 0.001(3) -0.023(3) C22 0.045(5) 0.046(5) 0.098(6) -0.001(4) 0.003(4) -0.015(4) C23 0.025(4) 0.036(4) 0.060(4) -0.001(3) 0.006(3) -0.004(3) N1 0.038(3) 0.045(3) 0.054(4) -0.003(3) -0.003(3) -0.011(3) N2 0.062(4) 0.058(4) 0.069(4) 0.019(3) -0.011(4) -0.023(3) N3 0.049(4) 0.052(4) 0.060(4) 0.005(3) -0.002(3) -0.019(3) N4 0.039(3) 0.043(4) 0.060(4) 0.011(3) -0.011(3) -0.011(3) N5 0.050(4) 0.049(4) 0.052(4) -0.007(3) 0.001(3) -0.012(3) N6 0.064(5) 0.049(4) 0.072(5) -0.004(3) -0.015(4) 0.005(3) O1 0.020(3) 0.054(3) 0.075(3) 0.003(2) -0.008(2) -0.011(2) O2 0.036(3) 0.042(3) 0.097(4) 0.006(3) 0.004(3) -0.015(2) O1W 0.096(6) 0.046(4) 0.194(8) -0.015(4) 0.015(6) -0.005(4) O3 0.023(3) 0.044(3) 0.164(6) 0.014(3) -0.003(3) -0.014(2) O2W 0.077(5) 0.076(5) 0.179(8) -0.038(5) 0.017(5) -0.016(4) O4 0.036(3) 0.043(3) 0.075(3) -0.003(2) -0.007(2) -0.018(2) O5 0.050(4) 0.047(4) 0.247(9) -0.024(5) 0.002(5) -0.017(3) O6 0.059(4) 0.051(4) 0.184(7) 0.009(4) -0.011(4) -0.012(3) _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 Zn1 O1 1.968(4) . ? Zn1 O4 1.981(5) 1_655 ? Zn1 N4 2.016(6) . ? Zn1 N1 2.056(5) . ? C1 N3 1.315(8) . ? C1 N1 1.322(8) . ? C1 H1 0.9300 . ? C2 N2 1.305(9) . ? C2 N1 1.336(8) . ? C2 H2 0.9300 . ? C3 N3 1.472(9) . ? C3 C4 1.496(10) . ? C3 H21A 0.9700 . ? C3 H21B 0.9700 . ? C4 C5 1.511(11) . ? C4 H22A 0.9700 . ? C4 H22B 0.9700 . ? C5 C6 1.494(11) . ? C5 H23A 0.9700 . ? C5 H23B 0.9700 . ? C6 C7 1.514(11) . ? C6 H15A 0.9700 . ? C6 H15B 0.9700 . ? C7 C7 1.523(15) 2_575 ? C7 H16A 0.9700 . ? C7 H16B 0.9700 . ? C8 N4 1.313(8) . ? C8 N5 1.324(8) . ? C8 H8 0.9300 . ? C9 N6 1.296(9) . ? C9 N4 1.367(9) . ? C9 H9 0.9300 . ? C10 N5 1.463(9) . ? C10 C11 1.508(10) . ? C10 H27A 0.9700 . ? C10 H27B 0.9700 . ? C11 C12 1.507(10) . ? C11 H28A 0.9700 . ? C11 H28B 0.9700 . ? C12 C13 1.509(11) . ? C12 H29A 0.9700 . ? C12 H29B 0.9700 . ? C13 C14 1.519(11) . ? C13 H30A 0.9700 . ? C13 H30B 0.9700 . ? C14 C14 1.521(16) 2_657 ? C14 H31A 0.9700 . ? C14 H31B 0.9700 . ? C15 C16 1.377(9) . ? C15 C20 1.389(9) . ? C15 C21 1.533(8) . ? C16 C17 1.401(8) . ? C16 H3 0.9300 . ? C17 C18 1.382(9) . ? C17 C22 1.502(10) . ? C18 C19 1.392(9) . ? C18 H5 0.9300 . ? C19 C20 1.383(8) . ? C19 C23 1.518(9) . ? C20 H7 0.9300 . ? C21 O2 1.232(8) . ? C21 O1 1.261(8) . ? C22 O6 1.208(9) . ? C22 O5 1.308(9) . ? C23 O3 1.225(8) . ? C23 O4 1.262(7) . ? N2 N3 1.358(8) . ? N5 N6 1.363(8) . ? O1W H1WA 0.86(3) . ? O1W H1WB 0.87(3) . ? O2W H2WA 0.86(3) . ? O2W H2WB 0.89(3) . ? O4 Zn1 1.981(5) 1_455 ? O5 H5WA 0.85(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O4 96.54(18) . 1_655 ? O1 Zn1 N4 117.9(2) . . ? O4 Zn1 N4 111.4(2) 1_655 . ? O1 Zn1 N1 113.8(2) . . ? O4 Zn1 N1 120.0(2) 1_655 . ? N4 Zn1 N1 98.5(2) . . ? N3 C1 N1 110.0(6) . . ? N3 C1 H1 125.0 . . ? N1 C1 H1 125.0 . . ? N2 C2 N1 115.3(7) . . ? N2 C2 H2 122.4 . . ? N1 C2 H2 122.4 . . ? N3 C3 C4 112.8(6) . . ? N3 C3 H21A 109.0 . . ? C4 C3 H21A 109.0 . . ? N3 C3 H21B 109.0 . . ? C4 C3 H21B 109.0 . . ? H21A C3 H21B 107.8 . . ? C3 C4 C5 113.1(7) . . ? C3 C4 H22A 109.0 . . ? C5 C4 H22A 109.0 . . ? C3 C4 H22B 109.0 . . ? C5 C4 H22B 109.0 . . ? H22A C4 H22B 107.8 . . ? C6 C5 C4 113.2(7) . . ? C6 C5 H23A 108.9 . . ? C4 C5 H23A 108.9 . . ? C6 C5 H23B 108.9 . . ? C4 C5 H23B 108.9 . . ? H23A C5 H23B 107.8 . . ? C5 C6 C7 114.9(7) . . ? C5 C6 H15A 108.5 . . ? C7 C6 H15A 108.5 . . ? C5 C6 H15B 108.5 . . ? C7 C6 H15B 108.5 . . ? H15A C6 H15B 107.5 . . ? C6 C7 C7 113.9(9) . 2_575 ? C6 C7 H16A 108.8 . . ? C7 C7 H16A 108.8 2_575 . ? C6 C7 H16B 108.8 . . ? C7 C7 H16B 108.8 2_575 . ? H16A C7 H16B 107.7 . . ? N4 C8 N5 110.2(6) . . ? N4 C8 H8 124.9 . . ? N5 C8 H8 124.9 . . ? N6 C9 N4 114.9(6) . . ? N6 C9 H9 122.5 . . ? N4 C9 H9 122.5 . . ? N5 C10 C11 111.8(6) . . ? N5 C10 H27A 109.3 . . ? C11 C10 H27A 109.3 . . ? N5 C10 H27B 109.3 . . ? C11 C10 H27B 109.3 . . ? H27A C10 H27B 107.9 . . ? C12 C11 C10 115.5(7) . . ? C12 C11 H28A 108.4 . . ? C10 C11 H28A 108.4 . . ? C12 C11 H28B 108.4 . . ? C10 C11 H28B 108.4 . . ? H28A C11 H28B 107.5 . . ? C11 C12 C13 115.2(7) . . ? C11 C12 H29A 108.5 . . ? C13 C12 H29A 108.5 . . ? C11 C12 H29B 108.5 . . ? C13 C12 H29B 108.5 . . ? H29A C12 H29B 107.5 . . ? C12 C13 C14 114.0(8) . . ? C12 C13 H30A 108.8 . . ? C14 C13 H30A 108.8 . . ? C12 C13 H30B 108.8 . . ? C14 C13 H30B 108.8 . . ? H30A C13 H30B 107.6 . . ? C13 C14 C14 113.1(9) . 2_657 ? C13 C14 H31A 109.0 . . ? C14 C14 H31A 109.0 2_657 . ? C13 C14 H31B 109.0 . . ? C14 C14 H31B 109.0 2_657 . ? H31A C14 H31B 107.8 . . ? C16 C15 C20 120.8(6) . . ? C16 C15 C21 120.2(6) . . ? C20 C15 C21 119.0(6) . . ? C15 C16 C17 118.7(6) . . ? C15 C16 H3 120.6 . . ? C17 C16 H3 120.6 . . ? C18 C17 C16 120.8(6) . . ? C18 C17 C22 121.7(6) . . ? C16 C17 C22 117.4(6) . . ? C17 C18 C19 119.8(6) . . ? C17 C18 H5 120.1 . . ? C19 C18 H5 120.1 . . ? C20 C19 C18 119.6(6) . . ? C20 C19 C23 118.7(6) . . ? C18 C19 C23 121.7(5) . . ? C19 C20 C15 120.2(6) . . ? C19 C20 H7 119.9 . . ? C15 C20 H7 119.9 . . ? O2 C21 O1 123.4(6) . . ? O2 C21 C15 118.7(6) . . ? O1 C21 C15 117.9(6) . . ? O6 C22 O5 122.6(7) . . ? O6 C22 C17 123.8(7) . . ? O5 C22 C17 113.5(7) . . ? O3 C23 O4 121.3(6) . . ? O3 C23 C19 118.9(6) . . ? O4 C23 C19 119.8(6) . . ? C1 N1 C2 102.8(6) . . ? C1 N1 Zn1 126.5(5) . . ? C2 N1 Zn1 127.3(5) . . ? C2 N2 N3 101.9(6) . . ? C1 N3 N2 110.0(6) . . ? C1 N3 C3 129.0(6) . . ? N2 N3 C3 120.9(6) . . ? C8 N4 C9 102.6(6) . . ? C8 N4 Zn1 127.5(5) . . ? C9 N4 Zn1 128.5(5) . . ? C8 N5 N6 110.0(6) . . ? C8 N5 C10 129.7(6) . . ? N6 N5 C10 120.2(6) . . ? C9 N6 N5 102.2(6) . . ? C21 O1 Zn1 109.5(4) . . ? H1WA O1W H1WB 102(4) . . ? H2WA O2W H2WB 101(4) . . ? C23 O4 Zn1 107.3(4) . 1_455 ? C22 O5 H5WA 112(8) . . ? 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 N3 C3 C4 C5 -171.8(7) . . . . ? C3 C4 C5 C6 -177.6(8) . . . . ? C4 C5 C6 C7 -171.5(8) . . . . ? C5 C6 C7 C7 179.2(10) . . . 2_575 ? N5 C10 C11 C12 68.1(9) . . . . ? C10 C11 C12 C13 68.2(9) . . . . ? C11 C12 C13 C14 167.6(7) . . . . ? C12 C13 C14 C14 -175.8(9) . . . 2_657 ? C20 C15 C16 C17 -0.1(10) . . . . ? C21 C15 C16 C17 -179.1(6) . . . . ? C15 C16 C17 C18 -1.3(10) . . . . ? C15 C16 C17 C22 175.9(7) . . . . ? C16 C17 C18 C19 1.9(10) . . . . ? C22 C17 C18 C19 -175.1(7) . . . . ? C17 C18 C19 C20 -1.1(10) . . . . ? C17 C18 C19 C23 178.3(6) . . . . ? C18 C19 C20 C15 -0.2(10) . . . . ? C23 C19 C20 C15 -179.7(6) . . . . ? C16 C15 C20 C19 0.9(10) . . . . ? C21 C15 C20 C19 179.9(6) . . . . ? C16 C15 C21 O2 -176.2(6) . . . . ? C20 C15 C21 O2 4.8(10) . . . . ? C16 C15 C21 O1 4.7(9) . . . . ? C20 C15 C21 O1 -174.3(6) . . . . ? C18 C17 C22 O6 179.2(8) . . . . ? C16 C17 C22 O6 2.0(12) . . . . ? C18 C17 C22 O5 0.2(12) . . . . ? C16 C17 C22 O5 -177.0(7) . . . . ? C20 C19 C23 O3 3.5(10) . . . . ? C18 C19 C23 O3 -176.0(7) . . . . ? C20 C19 C23 O4 -178.0(6) . . . . ? C18 C19 C23 O4 2.5(10) . . . . ? N3 C1 N1 C2 0.4(8) . . . . ? N3 C1 N1 Zn1 160.8(5) . . . . ? N2 C2 N1 C1 -0.6(9) . . . . ? N2 C2 N1 Zn1 -160.8(5) . . . . ? O1 Zn1 N1 C1 40.7(6) . . . . ? O4 Zn1 N1 C1 154.1(5) 1_655 . . . ? N4 Zn1 N1 C1 -85.1(6) . . . . ? O1 Zn1 N1 C2 -163.6(6) . . . . ? O4 Zn1 N1 C2 -50.1(7) 1_655 . . . ? N4 Zn1 N1 C2 70.7(6) . . . . ? N1 C2 N2 N3 0.5(9) . . . . ? N1 C1 N3 N2 -0.1(9) . . . . ? N1 C1 N3 C3 -177.2(7) . . . . ? C2 N2 N3 C1 -0.2(8) . . . . ? C2 N2 N3 C3 177.1(7) . . . . ? C4 C3 N3 C1 139.0(8) . . . . ? C4 C3 N3 N2 -37.7(11) . . . . ? N5 C8 N4 C9 0.7(8) . . . . ? N5 C8 N4 Zn1 167.7(4) . . . . ? N6 C9 N4 C8 -0.6(9) . . . . ? N6 C9 N4 Zn1 -167.4(5) . . . . ? O1 Zn1 N4 C8 98.7(6) . . . . ? O4 Zn1 N4 C8 -11.6(6) 1_655 . . . ? N1 Zn1 N4 C8 -138.5(6) . . . . ? O1 Zn1 N4 C9 -97.6(6) . . . . ? O4 Zn1 N4 C9 152.2(6) 1_655 . . . ? N1 Zn1 N4 C9 25.2(6) . . . . ? N4 C8 N5 N6 -0.7(8) . . . . ? N4 C8 N5 C10 175.9(6) . . . . ? C11 C10 N5 C8 -103.8(9) . . . . ? C11 C10 N5 N6 72.5(8) . . . . ? N4 C9 N6 N5 0.2(9) . . . . ? C8 N5 N6 C9 0.3(8) . . . . ? C10 N5 N6 C9 -176.6(6) . . . . ? O2 C21 O1 Zn1 0.6(8) . . . . ? C15 C21 O1 Zn1 179.7(4) . . . . ? O4 Zn1 O1 C21 174.9(4) 1_655 . . . ? N4 Zn1 O1 C21 56.4(5) . . . . ? N1 Zn1 O1 C21 -58.2(5) . . . . ? O3 C23 O4 Zn1 -2.6(8) . . . 1_455 ? C19 C23 O4 Zn1 178.9(5) . . . 1_455 ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 58.93 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.768 _refine_diff_density_min -0.907 _refine_diff_density_rms 0.102 _database_code_depnum_ccdc_archive 'CCDC 961129' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_c2c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H50 N12 O8 Zn2' _chemical_formula_weight 933.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.249(3) _cell_length_b 9.1097(3) _cell_length_c 18.2763(13) _cell_angle_alpha 90.00 _cell_angle_beta 122.814(11) _cell_angle_gamma 90.00 _cell_volume 4232.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1944 _exptl_absorpt_coefficient_mu 1.941 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8486 _diffrn_reflns_av_R_equivalents 0.0905 _diffrn_reflns_av_sigmaI/netI 0.0767 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 67.05 _reflns_number_total 3704 _reflns_number_gt 2336 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 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^)+(0.0971P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3704 _refine_ls_number_parameters 255 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1069 _refine_ls_R_factor_gt 0.0722 _refine_ls_wR_factor_ref 0.1908 _refine_ls_wR_factor_gt 0.1742 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 Zn1 Zn 0.26326(3) 0.79356(7) 0.70919(4) 0.0433(3) Uani 1 1 d . . . C1 C 0.3486(3) 0.5539(8) 0.7885(4) 0.0662(18) Uani 1 1 d . . . H022 H 0.3522 0.5581 0.8423 0.079 Uiso 1 1 calc R . . C2 C 0.3225(3) 0.5985(7) 0.6589(4) 0.0532(15) Uani 1 1 d . . . H016 H 0.3053 0.6378 0.6031 0.064 Uiso 1 1 calc R . . C3 C 0.3771(3) 0.4146(9) 0.6403(6) 0.078(2) Uani 1 1 d . . . H02A H 0.3916 0.3208 0.6683 0.094 Uiso 1 1 calc R . . H02B H 0.3480 0.3953 0.5813 0.094 Uiso 1 1 calc R . . C4 C 0.4163(4) 0.4943(11) 0.6375(8) 0.113(4) Uani 1 1 d . . . H02E H 0.4445 0.5166 0.6967 0.136 Uiso 1 1 calc R . . H02F H 0.4013 0.5868 0.6082 0.136 Uiso 1 1 calc R . . C5 C 0.4400(4) 0.4187(10) 0.5923(6) 0.089(3) Uani 1 1 d . . . H02G H 0.4652 0.3464 0.6319 0.106 Uiso 1 1 calc R . . H02H H 0.4122 0.3663 0.5421 0.106 Uiso 1 1 calc R . . C6 C 0.4658(4) 0.5143(11) 0.5638(7) 0.101(3) Uani 1 1 d . . . H02C H 0.4939 0.5651 0.6145 0.121 Uiso 1 1 calc R . . H02D H 0.4406 0.5880 0.5258 0.121 Uiso 1 1 calc R . . C7 C 0.4888(3) 0.4459(10) 0.5171(5) 0.079(2) Uani 1 1 d . . . H01A H 0.4617 0.3888 0.4686 0.095 Uiso 1 1 calc R . . H01B H 0.5165 0.3787 0.5565 0.095 Uiso 1 1 calc R . . C8 C 0.1623(3) 0.6429(9) 0.6481(5) 0.0706(19) Uani 1 1 d . . . H017 H 0.1713 0.6369 0.7054 0.085 Uiso 1 1 calc R . . C9 C 0.1620(3) 0.6872(9) 0.5375(4) 0.073(2) Uani 1 1 d . . . H021 H 0.1726 0.7211 0.5013 0.088 Uiso 1 1 calc R . . C10 C 0.0794(5) 0.4900(16) 0.5783(9) 0.143(4) Uiso 1 1 d . . . C11' C 0.0859(6) 0.467(2) 0.6670(11) 0.161(5) Uiso 1 1 d . . . C11 C 0.0706(9) 0.559(2) 0.6743(15) 0.110(6) Uiso 0.50 1 d PD . . C12 C 0.0452(9) 0.419(2) 0.6791(16) 0.125(7) Uiso 0.50 1 d PD . . C13 C 0.0538(10) 0.406(3) 0.7705(17) 0.120(7) Uiso 0.50 1 d P . . C13' C 0.0429(10) 0.504(3) 0.7695(18) 0.246(11) Uiso 1 1 d . . . C14 C 0.0000 0.389(5) 0.7500 0.29(2) Uani 1 2 d S . . C15 C 0.2651(2) 0.7536(5) 0.9391(3) 0.0395(12) Uani 1 1 d . . . C16 C 0.2441(2) 0.6258(5) 0.9508(3) 0.0397(12) Uani 1 1 d . . . C17 C 0.2389(3) 0.4849(6) 0.9036(4) 0.0506(15) Uani 1 1 d . . . C18 C 0.2701(2) 0.8764(6) 0.9886(3) 0.0436(13) Uani 1 1 d . . . H012 H 0.2835 0.9628 0.9807 0.052 Uiso 1 1 calc R . . C19 C 0.2850(3) 0.7633(6) 0.8797(4) 0.0489(15) Uani 1 1 d . . . N1 N 0.3570(2) 0.4917(6) 0.6873(4) 0.0588(13) Uani 1 1 d . . . N2 N 0.3753(3) 0.4617(7) 0.7717(4) 0.0766(17) Uani 1 1 d . . . N3 N 0.3155(2) 0.6425(5) 0.7214(3) 0.0491(12) Uani 1 1 d . . . N4 N 0.1907(2) 0.7083(6) 0.6240(3) 0.0533(12) Uani 1 1 d . . . N5 N 0.1188(3) 0.6165(10) 0.5086(4) 0.093(2) Uani 1 1 d . . . N6 N 0.1197(2) 0.5869(8) 0.5814(4) 0.0792(18) Uani 1 1 d . . . O1 O 0.25399(19) 0.8195(4) 0.8055(3) 0.0610(12) Uani 1 1 d . . . O2 O 0.3293(2) 0.7230(8) 0.9072(3) 0.099(2) Uani 1 1 d . . . O3 O 0.23239(18) 0.4921(4) 0.8289(2) 0.0562(11) Uani 1 1 d . . . O4 O 0.2426(3) 0.3681(5) 0.9401(3) 0.0855(18) Uani 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 Zn1 0.0757(6) 0.0344(4) 0.0385(4) 0.0045(3) 0.0431(4) 0.0021(4) C1 0.079(5) 0.071(4) 0.048(4) 0.005(3) 0.034(4) 0.019(4) C2 0.073(4) 0.057(4) 0.045(3) -0.003(3) 0.042(3) 0.003(3) C3 0.080(5) 0.084(5) 0.094(5) -0.023(4) 0.062(5) 0.007(4) C4 0.153(9) 0.111(7) 0.147(9) -0.041(7) 0.128(8) -0.023(7) C5 0.093(6) 0.113(7) 0.093(6) -0.029(5) 0.072(5) -0.016(5) C6 0.129(8) 0.110(7) 0.111(7) -0.010(6) 0.096(7) 0.003(6) C7 0.080(5) 0.107(6) 0.072(5) -0.012(4) 0.054(4) 0.003(4) C8 0.072(5) 0.089(5) 0.051(4) 0.018(4) 0.034(4) 0.000(4) C9 0.083(5) 0.092(6) 0.045(4) 0.008(4) 0.036(4) 0.011(5) C14 0.11(2) 0.32(5) 0.36(5) 0.000 0.08(3) 0.000 C15 0.067(4) 0.037(3) 0.025(2) 0.000(2) 0.032(3) 0.006(2) C16 0.076(4) 0.025(3) 0.032(2) -0.002(2) 0.038(3) 0.003(2) C17 0.091(5) 0.035(3) 0.042(3) -0.003(2) 0.047(3) -0.001(3) C18 0.074(4) 0.034(3) 0.039(3) -0.002(2) 0.042(3) -0.002(3) C19 0.077(5) 0.047(3) 0.043(3) -0.007(3) 0.046(4) -0.006(3) N1 0.057(3) 0.058(3) 0.071(4) -0.006(3) 0.041(3) 0.010(3) N2 0.084(4) 0.078(4) 0.061(4) 0.007(3) 0.035(3) 0.026(3) N3 0.071(3) 0.046(3) 0.043(3) -0.002(2) 0.039(3) -0.003(2) N4 0.076(3) 0.049(3) 0.041(2) 0.009(2) 0.036(3) 0.011(3) N5 0.086(5) 0.126(7) 0.056(4) -0.006(4) 0.031(4) -0.009(5) N6 0.057(4) 0.100(5) 0.063(4) 0.001(3) 0.022(3) -0.010(3) O1 0.107(4) 0.052(3) 0.049(2) 0.0177(18) 0.059(3) 0.018(2) O2 0.074(3) 0.190(7) 0.046(3) -0.009(3) 0.041(3) 0.021(4) O3 0.111(4) 0.040(2) 0.036(2) -0.0008(16) 0.052(2) 0.006(2) O4 0.190(6) 0.034(2) 0.068(3) -0.002(2) 0.093(4) -0.003(3) _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 Zn1 O1 1.940(3) . ? Zn1 O3 1.968(4) 4_556 ? Zn1 N3 2.015(5) . ? Zn1 N4 2.034(6) . ? C1 N2 1.310(9) . ? C1 N3 1.352(8) . ? C1 H022 0.9300 . ? C2 N1 1.312(8) . ? C2 N3 1.330(7) . ? C2 H016 0.9300 . ? C3 C4 1.416(12) . ? C3 N1 1.470(8) . ? C3 H02A 0.9700 . ? C3 H02B 0.9700 . ? C4 C5 1.518(10) . ? C4 H02E 0.9700 . ? C4 H02F 0.9700 . ? C5 C6 1.444(12) . ? C5 H02G 0.9700 . ? C5 H02H 0.9700 . ? C6 C7 1.498(10) . ? C6 H02C 0.9700 . ? C6 H02D 0.9700 . ? C7 C7 1.509(16) 5_666 ? C7 H01A 0.9700 . ? C7 H01B 0.9700 . ? C8 N4 1.303(8) . ? C8 N6 1.305(10) . ? C8 H017 0.9300 . ? C9 N5 1.288(10) . ? C9 N4 1.342(9) . ? C9 H021 0.9300 . ? C10 N6 1.481(15) . ? C10 C11' 1.54(2) . ? C10 C11 2.01(3) . ? C11' C11 1.00(2) . ? C11' C12 1.43(3) . ? C11 C12 1.515(10) . ? C12 C13 1.55(3) . ? C12 C13' 1.86(3) . ? C13 C13' 0.95(3) . ? C13 C14 1.47(3) . ? C13' C14 1.55(3) . ? C14 C13 1.47(3) 2_556 ? C14 C13' 1.55(3) 2_556 ? C15 C18 1.394(7) . ? C15 C16 1.396(7) . ? C15 C19 1.502(7) . ? C16 C18 1.390(6) 7_567 ? C16 C17 1.506(7) . ? C17 O4 1.228(7) . ? C17 O3 1.271(6) . ? C18 C16 1.390(6) 7_567 ? C18 H012 0.9300 . ? C19 O2 1.208(8) . ? C19 O1 1.267(7) . ? N1 N2 1.356(8) . ? N5 N6 1.342(9) . ? O3 Zn1 1.968(4) 4_546 ? 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 Zn1 O3 106.21(16) . 4_556 ? O1 Zn1 N3 118.24(17) . . ? O3 Zn1 N3 117.90(18) 4_556 . ? O1 Zn1 N4 96.57(19) . . ? O3 Zn1 N4 109.33(19) 4_556 . ? N3 Zn1 N4 106.3(2) . . ? N2 C1 N3 114.8(6) . . ? N2 C1 H022 122.6 . . ? N3 C1 H022 122.6 . . ? N1 C2 N3 110.3(5) . . ? N1 C2 H016 124.8 . . ? N3 C2 H016 124.8 . . ? C4 C3 N1 113.3(7) . . ? C4 C3 H02A 108.9 . . ? N1 C3 H02A 108.9 . . ? C4 C3 H02B 108.9 . . ? N1 C3 H02B 108.9 . . ? H02A C3 H02B 107.7 . . ? C3 C4 C5 116.0(8) . . ? C3 C4 H02E 108.3 . . ? C5 C4 H02E 108.3 . . ? C3 C4 H02F 108.3 . . ? C5 C4 H02F 108.3 . . ? H02E C4 H02F 107.4 . . ? C6 C5 C4 115.4(8) . . ? C6 C5 H02G 108.4 . . ? C4 C5 H02G 108.4 . . ? C6 C5 H02H 108.4 . . ? C4 C5 H02H 108.4 . . ? H02G C5 H02H 107.5 . . ? C5 C6 C7 117.7(8) . . ? C5 C6 H02C 107.9 . . ? C7 C6 H02C 107.9 . . ? C5 C6 H02D 107.9 . . ? C7 C6 H02D 107.9 . . ? H02C C6 H02D 107.2 . . ? C6 C7 C7 114.5(9) . 5_666 ? C6 C7 H01A 108.6 . . ? C7 C7 H01A 108.6 5_666 . ? C6 C7 H01B 108.6 . . ? C7 C7 H01B 108.6 5_666 . ? H01A C7 H01B 107.6 . . ? N4 C8 N6 111.1(6) . . ? N4 C8 H017 124.4 . . ? N6 C8 H017 124.4 . . ? N5 C9 N4 114.8(7) . . ? N5 C9 H021 122.6 . . ? N4 C9 H021 122.6 . . ? N6 C10 C11' 114.2(11) . . ? N6 C10 C11 106.0(10) . . ? C11' C10 C11 29.0(8) . . ? C11 C11' C12 74.8(14) . . ? C11 C11' C10 103(2) . . ? C12 C11' C10 125.3(17) . . ? C11' C11 C12 65.6(16) . . ? C11' C11 C10 48.3(15) . . ? C12 C11 C10 95.8(15) . . ? C11' C12 C11 39.5(11) . . ? C11' C12 C13 122(2) . . ? C11 C12 C13 109.5(19) . . ? C11' C12 C13' 117.4(17) . . ? C11 C12 C13' 88.1(16) . . ? C13 C12 C13' 30.6(13) . . ? C13' C13 C14 77(3) . . ? C13' C13 C12 93(3) . . ? C14 C13 C12 102.6(18) . . ? C13 C13' C14 67(3) . . ? C13 C13' C12 56(2) . . ? C14 C13' C12 86.8(15) . . ? C13 C14 C13 168(4) 2_556 . ? C13 C14 C13' 36.5(13) 2_556 2_556 ? C13 C14 C13' 132(4) . 2_556 ? C13 C14 C13' 132(4) 2_556 . ? C13 C14 C13' 36.5(13) . . ? C13' C14 C13' 95(4) 2_556 . ? C18 C15 C16 118.0(4) . . ? C18 C15 C19 118.4(5) . . ? C16 C15 C19 123.6(4) . . ? C18 C16 C15 119.8(5) 7_567 . ? C18 C16 C17 117.5(4) 7_567 . ? C15 C16 C17 122.6(4) . . ? O4 C17 O3 122.9(5) . . ? O4 C17 C16 118.5(4) . . ? O3 C17 C16 118.5(5) . . ? C16 C18 C15 122.2(5) 7_567 . ? C16 C18 H012 118.9 7_567 . ? C15 C18 H012 118.9 . . ? O2 C19 O1 125.3(5) . . ? O2 C19 C15 118.2(5) . . ? O1 C19 C15 116.4(5) . . ? C2 N1 N2 110.2(5) . . ? C2 N1 C3 128.1(6) . . ? N2 N1 C3 121.7(6) . . ? C1 N2 N1 102.4(5) . . ? C2 N3 C1 102.4(5) . . ? C2 N3 Zn1 126.2(4) . . ? C1 N3 Zn1 131.2(4) . . ? C8 N4 C9 102.0(6) . . ? C8 N4 Zn1 123.4(4) . . ? C9 N4 Zn1 134.2(5) . . ? C9 N5 N6 102.8(6) . . ? C8 N6 N5 109.1(6) . . ? C8 N6 C10 130.1(8) . . ? N5 N6 C10 120.4(8) . . ? C19 O1 Zn1 122.4(4) . . ? C17 O3 Zn1 109.3(3) . 4_546 ? 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 N1 C3 C4 C5 178.2(9) . . . . ? C3 C4 C5 C6 160.1(10) . . . . ? C4 C5 C6 C7 -178.7(9) . . . . ? C5 C6 C7 C7 175.2(10) . . . 5_666 ? N6 C10 C11' C11 79(2) . . . . ? N6 C10 C11' C12 159.5(17) . . . . ? C11 C10 C11' C12 80(2) . . . . ? C10 C11' C11 C12 123.5(17) . . . . ? C12 C11' C11 C10 -123.5(17) . . . . ? N6 C10 C11 C11' -111(2) . . . . ? N6 C10 C11 C12 -161.0(14) . . . . ? C11' C10 C11 C12 -49.8(18) . . . . ? C10 C11' C12 C11 -95(2) . . . . ? C11 C11' C12 C13 -82(3) . . . . ? C10 C11' C12 C13 -176.5(19) . . . . ? C11 C11' C12 C13' -47(2) . . . . ? C10 C11' C12 C13' -141.5(18) . . . . ? C10 C11 C12 C11' 38.7(15) . . . . ? C11' C11 C12 C13 118(2) . . . . ? C10 C11 C12 C13 156.3(17) . . . . ? C11' C11 C12 C13' 140(2) . . . . ? C10 C11 C12 C13' 178.6(13) . . . . ? C11' C12 C13 C13' 90(3) . . . . ? C11 C12 C13 C13' 48(3) . . . . ? C11' C12 C13 C14 167(3) . . . . ? C11 C12 C13 C14 125(3) . . . . ? C13' C12 C13 C14 77(3) . . . . ? C12 C13 C13' C14 102.2(16) . . . . ? C14 C13 C13' C12 -102.2(16) . . . . ? C11' C12 C13' C13 -108(3) . . . . ? C11 C12 C13' C13 -135(3) . . . . ? C11' C12 C13' C14 -172(2) . . . . ? C11 C12 C13' C14 160(2) . . . . ? C13 C12 C13' C14 -64(3) . . . . ? C13' C13 C14 C13 3(2) . . . 2_556 ? C12 C13 C14 C13 -86.9(16) . . . 2_556 ? C13' C13 C14 C13' 6(4) . . . 2_556 ? C12 C13 C14 C13' -84(3) . . . 2_556 ? C12 C13 C14 C13' -90(3) . . . . ? C13 C13' C14 C13 -179.1(7) . . . 2_556 ? C12 C13' C14 C13 -124.6(18) . . . 2_556 ? C12 C13' C14 C13 54(2) . . . . ? C13 C13' C14 C13' -175(3) . . . 2_556 ? C12 C13' C14 C13' -121.0(17) . . . 2_556 ? C18 C15 C16 C18 -1.1(9) . . . 7_567 ? C19 C15 C16 C18 175.7(5) . . . 7_567 ? C18 C15 C16 C17 -177.5(6) . . . . ? C19 C15 C16 C17 -0.7(9) . . . . ? C18 C16 C17 O4 -27.8(9) 7_567 . . . ? C15 C16 C17 O4 148.7(7) . . . . ? C18 C16 C17 O3 154.3(6) 7_567 . . . ? C15 C16 C17 O3 -29.2(9) . . . . ? C16 C15 C18 C16 1.1(9) . . . 7_567 ? C19 C15 C18 C16 -175.8(5) . . . 7_567 ? C18 C15 C19 O2 93.3(8) . . . . ? C16 C15 C19 O2 -83.5(8) . . . . ? C18 C15 C19 O1 -83.9(7) . . . . ? C16 C15 C19 O1 99.3(7) . . . . ? N3 C2 N1 N2 -0.9(8) . . . . ? N3 C2 N1 C3 -178.2(6) . . . . ? C4 C3 N1 C2 79.3(11) . . . . ? C4 C3 N1 N2 -97.7(10) . . . . ? N3 C1 N2 N1 -1.3(9) . . . . ? C2 N1 N2 C1 1.3(8) . . . . ? C3 N1 N2 C1 178.8(6) . . . . ? N1 C2 N3 C1 0.1(7) . . . . ? N1 C2 N3 Zn1 -175.6(4) . . . . ? N2 C1 N3 C2 0.7(8) . . . . ? N2 C1 N3 Zn1 176.2(5) . . . . ? O1 Zn1 N3 C2 171.7(5) . . . . ? O3 Zn1 N3 C2 -58.3(5) 4_556 . . . ? N4 Zn1 N3 C2 64.7(5) . . . . ? O1 Zn1 N3 C1 -2.7(7) . . . . ? O3 Zn1 N3 C1 127.3(6) 4_556 . . . ? N4 Zn1 N3 C1 -109.7(6) . . . . ? N6 C8 N4 C9 -0.1(9) . . . . ? N6 C8 N4 Zn1 -174.3(5) . . . . ? N5 C9 N4 C8 0.9(9) . . . . ? N5 C9 N4 Zn1 174.0(6) . . . . ? O1 Zn1 N4 C8 -23.6(6) . . . . ? O3 Zn1 N4 C8 -133.3(5) 4_556 . . . ? N3 Zn1 N4 C8 98.4(6) . . . . ? O1 Zn1 N4 C9 164.5(6) . . . . ? O3 Zn1 N4 C9 54.7(7) 4_556 . . . ? N3 Zn1 N4 C9 -73.6(7) . . . . ? N4 C9 N5 N6 -1.2(10) . . . . ? N4 C8 N6 N5 -0.6(10) . . . . ? N4 C8 N6 C10 172.3(9) . . . . ? C9 N5 N6 C8 1.0(9) . . . . ? C9 N5 N6 C10 -172.7(9) . . . . ? C11' C10 N6 C8 7.7(18) . . . . ? C11 C10 N6 C8 37.4(15) . . . . ? C11' C10 N6 N5 179.9(10) . . . . ? C11 C10 N6 N5 -150.3(10) . . . . ? O2 C19 O1 Zn1 20.5(9) . . . . ? C15 C19 O1 Zn1 -162.5(4) . . . . ? O3 Zn1 O1 C19 -123.6(5) 4_556 . . . ? N3 Zn1 O1 C19 11.6(5) . . . . ? N4 Zn1 O1 C19 124.1(5) . . . . ? O4 C17 O3 Zn1 -5.6(8) . . . 4_546 ? C16 C17 O3 Zn1 172.2(5) . . . 4_546 ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.967 _refine_diff_density_min -0.563 _refine_diff_density_rms 0.127 _database_code_depnum_ccdc_archive 'CCDC 961130' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_comp6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H34 Cd N6 O7' _chemical_formula_weight 606.95 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'p -1' _symmetry_space_group_name_hall '-p 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1490(7) _cell_length_b 10.4230(7) _cell_length_c 14.5960(10) _cell_angle_alpha 75.494(6) _cell_angle_beta 81.455(6) _cell_angle_gamma 66.286(7) _cell_volume 1366.58(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4594 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 29.1 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.849 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.771 _exptl_absorpt_correction_T_max 0.813 _exptl_absorpt_process_details ? _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10029 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 29.12 _reflns_number_total 6170 _reflns_number_gt 4594 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 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^)+(0.0593P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6170 _refine_ls_number_parameters 335 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0950 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.969 _refine_ls_shift/su_max 0.050 _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 Cd1 Cd 0.61537(2) 0.21886(2) 0.413267(19) 0.04163(10) Uani 1 1 d . . . C1 C 0.5648(4) 0.3061(3) 0.6174(3) 0.0509(9) Uani 1 1 d . . . H1 H 0.5612 0.3971 0.5868 0.061 Uiso 1 1 calc R . . C2 C 0.5860(5) 0.0938(4) 0.6476(3) 0.0753(13) Uani 1 1 d . . . H2 H 0.6007 0.0032 0.6397 0.090 Uiso 1 1 calc R . . C3 C 0.5248(6) 0.3458(5) 0.7828(3) 0.0782(13) Uani 1 1 d . . . H3A H 0.4543 0.3257 0.8306 0.094 Uiso 1 1 calc R . . H3B H 0.4866 0.4477 0.7552 0.094 Uiso 1 1 calc R . . C4 C 0.6614(8) 0.3079(8) 0.8287(5) 0.123(2) Uani 1 1 d . . . H4A H 0.7364 0.3137 0.7801 0.148 Uiso 1 1 calc R . . H4B H 0.6917 0.2099 0.8648 0.148 Uiso 1 1 calc R . . C5 C 0.6426(11) 0.4068(12) 0.8937(7) 0.178(4) Uani 1 1 d . . . H5A H 0.5452 0.4784 0.8897 0.214 Uiso 1 1 calc R . . H5B H 0.6526 0.3514 0.9583 0.214 Uiso 1 1 calc R . . C6 C 0.7332(13) 0.4737(11) 0.8767(7) 0.191(5) Uani 1 1 d . . . H6A H 0.7208 0.5299 0.8123 0.229 Uiso 1 1 calc R . . H6B H 0.8301 0.4011 0.8782 0.229 Uiso 1 1 calc R . . C7 C 0.7255(13) 0.5719(12) 0.9398(7) 0.189(4) Uani 1 1 d . . . C8' C 0.759(2) 0.6954(19) 0.8787(11) 0.132(5) Uiso 0.50 1 d PD . . C8 C 0.835(3) 0.644(2) 0.9083(17) 0.174(8) Uiso 0.50 1 d PD . . C9 C 0.742(2) 0.797(2) 0.9492(14) 0.345(10) Uiso 1 1 d D . . C10 C 0.851(2) 0.835(3) 0.9714(15) 0.193(8) Uiso 0.50 1 d PD . . C10' C 0.818(2) 0.742(2) 1.0298(13) 0.184(7) Uiso 0.50 1 d PD . . C11 C 0.821(3) 0.862(3) 1.0813(15) 0.186(9) Uiso 0.50 1 d PD . . C11' C 0.840(3) 0.933(3) 1.0546(16) 0.177(8) Uiso 0.50 1 d P . . C12 C 0.7010(13) 0.9984(12) 1.0687(8) 0.175(3) Uiso 1 1 d . . . C13 C 0.6535(6) 1.0919(6) 1.2249(4) 0.0853(15) Uani 1 1 d D . . C14 C 0.7810(8) 1.2141(8) 1.1990(4) 0.121(2) Uani 1 1 d D . . C15 C 0.1610(3) 0.4144(3) 0.3867(2) 0.0336(6) Uani 1 1 d . . . C16 C 0.0727(3) 0.3394(3) 0.3909(2) 0.0357(7) Uani 1 1 d . . . H16 H 0.1124 0.2400 0.4002 0.043 Uiso 1 1 calc R . . C17 C -0.0743(3) 0.4132(3) 0.3813(2) 0.0362(7) Uani 1 1 d . . . C18 C -0.1327(3) 0.5621(3) 0.3641(2) 0.0404(7) Uani 1 1 d . . . H18 H -0.2307 0.6119 0.3553 0.048 Uiso 1 1 calc R . . C19 C -0.0443(3) 0.6361(3) 0.3601(2) 0.0400(7) Uani 1 1 d . . . C20 C 0.1009(3) 0.5626(3) 0.3724(2) 0.0376(7) Uani 1 1 d . . . H20 H 0.1592 0.6128 0.3712 0.045 Uiso 1 1 calc R . . C21 C 0.3201(3) 0.3395(3) 0.3955(2) 0.0377(7) Uani 1 1 d . . . C22 C -0.1719(3) 0.3335(3) 0.3920(2) 0.0406(7) Uani 1 1 d . . . O1 O 0.3932(2) 0.4112(2) 0.3933(2) 0.0548(7) Uani 1 1 d . . . O2 O 0.3787(2) 0.2061(2) 0.40185(19) 0.0494(6) Uani 1 1 d . . . O3 O -0.1235(2) 0.1998(2) 0.41980(19) 0.0524(6) Uani 1 1 d . . . O4 O -0.3015(2) 0.4034(2) 0.3746(2) 0.0593(7) Uani 1 1 d . . . O5 O -0.1059(2) 0.7833(2) 0.3428(2) 0.0599(7) Uani 1 1 d D . . N1 N 0.5888(3) 0.2008(3) 0.5738(2) 0.0480(7) Uani 1 1 d . . . N2 N 0.5616(5) 0.1262(4) 0.7301(3) 0.0877(13) Uani 1 1 d . . . N3 N 0.5469(4) 0.2656(3) 0.7089(3) 0.0578(8) Uani 1 1 d . . . N4 N 0.7637(18) 1.0520(12) 1.1528(8) 0.106(4) Uani 0.50 1 d P . . N4' N 0.6958(11) 1.0961(11) 1.1397(8) 0.074(3) Uiso 0.50 1 d P . . N5 N 0.8394(14) 1.1278(16) 1.1360(8) 0.094(3) Uani 0.50 1 d P . . N5' N 0.7689(17) 1.1897(15) 1.1147(11) 0.122(6) Uiso 0.50 1 d P . . N6 N 0.6836(4) 1.1787(3) 1.2622(2) 0.0625(9) Uani 1 1 d . . . O1W O 0.6849(3) -0.0282(3) 0.4481(2) 0.0708(9) Uani 1 1 d . . . O2W O 0.0464(3) 0.9146(3) 0.3873(2) 0.0701(8) Uani 1 1 d D . . H1WA H 0.745(6) -0.078(6) 0.423(4) 0.105 Uiso 1 1 d . . . H1WB H 0.656(6) -0.088(6) 0.500(4) 0.105 Uiso 1 1 d . . . H2WA H 0.068(6) 0.887(5) 0.4436(18) 0.105 Uiso 1 1 d D . . H2WB H 0.001(5) 1.001(2) 0.373(3) 0.105 Uiso 1 1 d D . . H5WA H -0.043(4) 0.816(5) 0.347(4) 0.105 Uiso 1 1 d 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 Cd1 0.02368(12) 0.03320(13) 0.0700(2) -0.01291(10) -0.00352(10) -0.01129(8) C1 0.050(2) 0.0357(16) 0.068(3) -0.0116(16) -0.0170(18) -0.0120(14) C2 0.115(4) 0.050(2) 0.082(3) -0.025(2) 0.014(3) -0.052(2) C3 0.110(4) 0.069(3) 0.068(3) -0.027(2) -0.011(3) -0.037(3) C4 0.145(6) 0.168(6) 0.093(5) -0.059(4) -0.005(4) -0.080(5) C5 0.180(9) 0.277(12) 0.154(8) -0.130(8) -0.006(6) -0.115(9) C6 0.283(13) 0.187(9) 0.174(9) -0.113(7) 0.066(9) -0.145(9) C7 0.239(11) 0.221(10) 0.175(9) -0.121(8) 0.043(8) -0.129(9) C13 0.119(4) 0.089(3) 0.070(3) -0.025(3) 0.001(3) -0.059(3) C14 0.158(6) 0.173(6) 0.089(4) -0.055(4) 0.042(4) -0.122(6) C15 0.0230(13) 0.0322(14) 0.0488(19) -0.0106(12) -0.0014(12) -0.0126(11) C16 0.0237(13) 0.0309(14) 0.056(2) -0.0119(13) -0.0036(13) -0.0114(11) C17 0.0257(14) 0.0342(14) 0.053(2) -0.0100(13) -0.0040(13) -0.0140(11) C18 0.0224(14) 0.0372(15) 0.060(2) -0.0115(14) -0.0048(13) -0.0081(11) C19 0.0294(15) 0.0299(14) 0.060(2) -0.0122(13) -0.0027(14) -0.0088(12) C20 0.0273(14) 0.0334(14) 0.059(2) -0.0145(13) -0.0015(14) -0.0158(12) C21 0.0245(14) 0.0326(14) 0.058(2) -0.0106(13) -0.0017(13) -0.0125(12) C22 0.0264(15) 0.0408(16) 0.060(2) -0.0148(14) -0.0030(14) -0.0161(12) O1 0.0265(11) 0.0349(11) 0.108(2) -0.0145(12) -0.0111(12) -0.0151(9) O2 0.0258(10) 0.0285(10) 0.0935(19) -0.0155(11) -0.0037(11) -0.0082(8) O3 0.0382(12) 0.0354(12) 0.0874(19) -0.0053(11) -0.0132(12) -0.0189(10) O4 0.0258(11) 0.0450(12) 0.110(2) -0.0130(13) -0.0115(12) -0.0152(10) O5 0.0345(12) 0.0295(11) 0.111(2) -0.0141(12) -0.0096(13) -0.0062(9) N1 0.0410(15) 0.0396(14) 0.071(2) -0.0173(14) -0.0059(14) -0.0193(12) N2 0.136(4) 0.059(2) 0.084(3) -0.0171(19) 0.014(3) -0.060(2) N3 0.067(2) 0.0421(15) 0.072(2) -0.0166(15) -0.0070(17) -0.0240(15) N4 0.137(11) 0.081(7) 0.096(8) -0.049(6) -0.030(8) -0.012(8) N5 0.099(8) 0.118(9) 0.079(7) -0.046(6) 0.024(6) -0.051(8) N6 0.064(2) 0.0611(19) 0.072(2) -0.0152(16) 0.0006(17) -0.0340(17) O1W 0.0692(19) 0.0356(13) 0.088(2) -0.0147(12) 0.0168(16) -0.0061(12) O2W 0.0658(18) 0.0462(14) 0.102(2) -0.0179(15) -0.0223(17) -0.0176(13) _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 Cd1 N1 2.287(3) . ? Cd1 N6 2.300(3) 1_544 ? Cd1 O4 2.313(2) 1_655 ? Cd1 O1W 2.319(2) . ? Cd1 O1 2.336(2) . ? Cd1 O2 2.491(2) . ? Cd1 O3 2.591(2) 1_655 ? C1 N3 1.303(5) . ? C1 N1 1.326(4) . ? C1 H1 0.9300 . ? C2 N2 1.293(6) . ? C2 N1 1.349(5) . ? C2 H2 0.9300 . ? C3 N3 1.464(5) . ? C3 C4 1.493(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.509(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.325(11) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.512(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8' 1.504(18) . ? C7 C8 1.53(2) . ? C8' C8 0.84(3) . ? C8' C9 1.601(16) . ? C8 C9 1.701(17) . ? C9 C10' 1.372(16) . ? C9 C10 1.415(17) . ? C10 C10' 1.25(3) . ? C10 C11 1.662(17) . ? C10 C11' 1.74(3) . ? C10' C11 1.634(17) . ? C11 C11' 0.82(3) . ? C11 C12 1.44(3) . ? C11' C12 1.31(2) . ? C12 N4' 1.606(15) . ? C12 N4 1.756(16) . ? C13 N4' 1.250(12) . ? C13 N6 1.314(5) . ? C13 N4 1.423(14) . ? C14 N6 1.347(6) . ? C14 N5' 1.350(16) . ? C14 N5 1.352(12) . ? C15 C20 1.386(4) . ? C15 C16 1.393(4) . ? C15 C21 1.494(4) . ? C16 C17 1.387(4) . ? C16 H16 0.9300 . ? C17 C18 1.390(4) . ? C17 C22 1.498(4) . ? C18 C19 1.386(4) . ? C18 H18 0.9300 . ? C19 O5 1.374(3) . ? C19 C20 1.376(4) . ? C20 H20 0.9300 . ? C21 O1 1.239(3) . ? C21 O2 1.258(3) . ? C22 O4 1.250(4) . ? C22 O3 1.255(4) . ? O3 Cd1 2.591(2) 1_455 ? O4 Cd1 2.313(2) 1_455 ? O5 H5WA 0.85(2) . ? N2 N3 1.358(4) . ? N4 N4' 0.680(15) . ? N4 N5 1.269(15) . ? N4 N5' 1.42(2) . ? N4' N5' 1.400(18) . ? N4' N5 1.610(16) . ? N5 N5' 0.787(17) . ? N6 Cd1 2.300(3) 1_566 ? O1W H1WA 0.74(6) . ? O1W H1WB 0.95(6) . ? O2W H2WA 0.832(19) . ? O2W H2WB 0.816(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cd1 N6 165.51(11) . 1_544 ? N1 Cd1 O4 97.72(10) . 1_655 ? N6 Cd1 O4 89.16(10) 1_544 1_655 ? N1 Cd1 O1W 85.66(11) . . ? N6 Cd1 O1W 81.38(11) 1_544 . ? O4 Cd1 O1W 144.36(10) 1_655 . ? N1 Cd1 O1 90.89(10) . . ? N6 Cd1 O1 102.77(11) 1_544 . ? O4 Cd1 O1 81.65(7) 1_655 . ? O1W Cd1 O1 133.92(9) . . ? N1 Cd1 O2 94.24(9) . . ? N6 Cd1 O2 90.12(10) 1_544 . ? O4 Cd1 O2 133.60(7) 1_655 . ? O1W Cd1 O2 81.00(10) . . ? O1 Cd1 O2 53.41(6) . . ? N1 Cd1 O3 88.40(9) . 1_655 ? N6 Cd1 O3 85.69(10) 1_544 1_655 ? O4 Cd1 O3 52.53(7) 1_655 1_655 ? O1W Cd1 O3 92.35(9) . 1_655 ? O1 Cd1 O3 133.54(7) . 1_655 ? O2 Cd1 O3 172.62(6) . 1_655 ? N3 C1 N1 111.2(3) . . ? N3 C1 H1 124.4 . . ? N1 C1 H1 124.4 . . ? N2 C2 N1 115.3(3) . . ? N2 C2 H2 122.3 . . ? N1 C2 H2 122.3 . . ? N3 C3 C4 111.9(4) . . ? N3 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N3 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C5 111.4(6) . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C6 C5 C4 115.9(8) . . ? C6 C5 H5A 108.3 . . ? C4 C5 H5A 108.3 . . ? C6 C5 H5B 108.3 . . ? C4 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? C5 C6 C7 119.8(8) . . ? C5 C6 H6A 107.4 . . ? C7 C6 H6A 107.4 . . ? C5 C6 H6B 107.4 . . ? C7 C6 H6B 107.4 . . ? H6A C6 H6B 106.9 . . ? C8' C7 C6 107.8(9) . . ? C8' C7 C8 32.2(10) . . ? C6 C7 C8 113.0(10) . . ? C8 C8' C7 76(2) . . ? C8 C8' C9 81.9(15) . . ? C7 C8' C9 104.8(12) . . ? C8' C8 C7 72(2) . . ? C8' C8 C9 68.7(14) . . ? C7 C8 C9 99.0(14) . . ? C10' C9 C10 53.1(13) . . ? C10' C9 C8' 119.4(15) . . ? C10 C9 C8' 126.6(18) . . ? C10' C9 C8 91.3(15) . . ? C10 C9 C8 104.1(17) . . ? C8' C9 C8 29.3(10) . . ? C10' C10 C9 61.7(11) . . ? C10' C10 C11 66.6(11) . . ? C9 C10 C11 110.1(16) . . ? C10' C10 C11' 94.5(15) . . ? C9 C10 C11' 127.7(18) . . ? C11 C10 C11' 27.9(11) . . ? C10 C10' C9 65.2(12) . . ? C10 C10' C11 69.0(12) . . ? C9 C10' C11 114.1(17) . . ? C11' C11 C12 64(3) . . ? C11' C11 C10' 126(3) . . ? C12 C11 C10' 117.3(18) . . ? C11' C11 C10 81(2) . . ? C12 C11 C10 100.6(16) . . ? C10' C11 C10 44.4(11) . . ? C11 C11' C12 82(3) . . ? C11 C11' C10 71(2) . . ? C12 C11' C10 102.6(17) . . ? C11' C12 C11 34.5(13) . . ? C11' C12 N4' 101.0(13) . . ? C11 C12 N4' 113.5(11) . . ? C11' C12 N4 79.8(13) . . ? C11 C12 N4 91.2(11) . . ? N4' C12 N4 22.8(5) . . ? N4' C13 N6 113.1(6) . . ? N4' C13 N4 28.6(6) . . ? N6 C13 N4 105.7(7) . . ? N6 C14 N5' 108.7(8) . . ? N6 C14 N5 113.9(6) . . ? N5' C14 N5 33.9(7) . . ? C20 C15 C16 119.6(2) . . ? C20 C15 C21 118.7(2) . . ? C16 C15 C21 121.7(2) . . ? C17 C16 C15 119.9(2) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.0(2) . . ? C16 C17 C22 120.5(2) . . ? C18 C17 C22 119.5(3) . . ? C19 C18 C17 119.8(3) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? O5 C19 C20 121.7(2) . . ? O5 C19 C18 118.2(3) . . ? C20 C19 C18 120.2(2) . . ? C19 C20 C15 120.5(2) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? O1 C21 O2 121.0(3) . . ? O1 C21 C15 119.1(2) . . ? O2 C21 C15 119.9(2) . . ? O4 C22 O3 121.4(2) . . ? O4 C22 C17 118.6(3) . . ? O3 C22 C17 120.0(3) . . ? C21 O1 Cd1 96.66(17) . . ? C21 O2 Cd1 88.88(16) . . ? C22 O3 Cd1 86.40(17) . 1_455 ? C22 O4 Cd1 99.61(18) . 1_455 ? C19 O5 H5WA 110(4) . . ? C1 N1 C2 101.5(3) . . ? C1 N1 Cd1 125.4(2) . . ? C2 N1 Cd1 133.1(2) . . ? C2 N2 N3 102.7(3) . . ? C1 N3 N2 109.3(3) . . ? C1 N3 C3 128.8(3) . . ? N2 N3 C3 121.8(4) . . ? N4' N4 N5 107.5(19) . . ? N4' N4 C13 61.4(17) . . ? N5 N4 C13 111.8(8) . . ? N4' N4 N5' 74.2(16) . . ? N5 N4 N5' 33.4(8) . . ? C13 N4 N5' 97.5(9) . . ? N4' N4 C12 66.2(16) . . ? N5 N4 C12 126.7(11) . . ? C13 N4 C12 109.6(12) . . ? N5' N4 C12 110.0(10) . . ? N4 N4' C13 90.0(18) . . ? N4 N4' N5' 77.9(18) . . ? C13 N4' N5' 107.6(11) . . ? N4 N4' C12 91.0(17) . . ? C13 N4' C12 131.2(9) . . ? N5' N4' C12 120.4(11) . . ? N4 N4' N5 48.7(16) . . ? C13 N4' N5 101.8(8) . . ? N5' N4' N5 29.3(7) . . ? C12 N4' N5 115.0(9) . . ? N5' N5 N4 84.1(18) . . ? N5' N5 C14 72.9(16) . . ? N4 N5 C14 102.6(9) . . ? N5' N5 N4' 60.4(16) . . ? N4 N5 N4' 23.8(7) . . ? C14 N5 N4' 92.7(8) . . ? N5 N5' C14 73.2(17) . . ? N5 N5' N4' 90.3(18) . . ? C14 N5' N4' 102.8(11) . . ? N5 N5' N4 62.5(15) . . ? C14 N5' N4 95.0(11) . . ? N4' N5' N4 27.9(7) . . ? C13 N6 C14 103.6(4) . . ? C13 N6 Cd1 125.8(3) . 1_566 ? C14 N6 Cd1 129.6(3) . 1_566 ? Cd1 O1W H1WA 125(4) . . ? Cd1 O1W H1WB 130(3) . . ? H1WA O1W H1WB 105(5) . . ? H2WA O2W H2WB 113(3) . . ? 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 N3 C3 C4 C5 171.2(6) . . . . ? C3 C4 C5 C6 -124.6(10) . . . . ? C4 C5 C6 C7 -178.3(10) . . . . ? C5 C6 C7 C8' -144.2(14) . . . . ? C5 C6 C7 C8 -178.2(15) . . . . ? C6 C7 C8' C8 -105.0(18) . . . . ? C6 C7 C8' C9 177.5(12) . . . . ? C8 C7 C8' C9 -77.5(16) . . . . ? C9 C8' C8 C7 107.6(11) . . . . ? C7 C8' C8 C9 -107.6(11) . . . . ? C6 C7 C8 C8' 87.1(19) . . . . ? C8' C7 C8 C9 64.1(14) . . . . ? C6 C7 C8 C9 151.2(13) . . . . ? C8 C8' C9 C10' -18(3) . . . . ? C7 C8' C9 C10' 55(2) . . . . ? C8 C8' C9 C10 46(3) . . . . ? C7 C8' C9 C10 118(2) . . . . ? C7 C8' C9 C8 73(2) . . . . ? C8' C8 C9 C10' 164(3) . . . . ? C7 C8 C9 C10' 97.5(19) . . . . ? C8' C8 C9 C10 -144(3) . . . . ? C7 C8 C9 C10 149.6(17) . . . . ? C7 C8 C9 C8' -67(2) . . . . ? C8' C9 C10 C10' -102(2) . . . . ? C8 C9 C10 C10' -80.8(17) . . . . ? C10' C9 C10 C11 -47.4(15) . . . . ? C8' C9 C10 C11 -149.3(19) . . . . ? C8 C9 C10 C11 -128.2(18) . . . . ? C10' C9 C10 C11' -72(2) . . . . ? C8' C9 C10 C11' -174.2(18) . . . . ? C8 C9 C10 C11' -153(2) . . . . ? C11 C10 C10' C9 131.1(18) . . . . ? C11' C10 C10' C9 130.9(18) . . . . ? C9 C10 C10' C11 -131.1(18) . . . . ? C11' C10 C10' C11 -0.2(17) . . . . ? C8' C9 C10' C10 116(2) . . . . ? C8 C9 C10' C10 106.8(17) . . . . ? C10 C9 C10' C11 50.3(17) . . . . ? C8' C9 C10' C11 166.0(18) . . . . ? C8 C9 C10' C11 157.1(18) . . . . ? C10 C10' C11 C11' 1(4) . . . . ? C9 C10' C11 C11' -48(5) . . . . ? C10 C10' C11 C12 77(2) . . . . ? C9 C10' C11 C12 28(3) . . . . ? C9 C10' C11 C10 -48.5(16) . . . . ? C10' C10 C11 C11' -179(4) . . . . ? C9 C10 C11 C11' -135(3) . . . . ? C10' C10 C11 C12 -118(2) . . . . ? C9 C10 C11 C12 -74(2) . . . . ? C11' C10 C11 C12 61(3) . . . . ? C9 C10 C11 C10' 44.9(15) . . . . ? C11' C10 C11 C10' 179(4) . . . . ? C10' C11 C11' C12 106(3) . . . . ? C10 C11 C11' C12 106.5(14) . . . . ? C12 C11 C11' C10 -106.5(14) . . . . ? C10' C11 C11' C10 0(3) . . . . ? C10' C10 C11' C11 0(3) . . . . ? C9 C10 C11' C11 58(4) . . . . ? C10' C10 C11' C12 -76(2) . . . . ? C9 C10 C11' C12 -19(3) . . . . ? C11 C10 C11' C12 -77(3) . . . . ? C10 C11' C12 C11 68(2) . . . . ? C11 C11' C12 N4' 116(2) . . . . ? C10 C11' C12 N4' -176.0(13) . . . . ? C11 C11' C12 N4 107(2) . . . . ? C10 C11' C12 N4 175.5(16) . . . . ? C10' C11 C12 C11' -118(3) . . . . ? C10 C11 C12 C11' -75(2) . . . . ? C11' C11 C12 N4' -75(3) . . . . ? C10' C11 C12 N4' 167.1(14) . . . . ? C10 C11 C12 N4' -149.1(11) . . . . ? C11' C11 C12 N4 -70(2) . . . . ? C10' C11 C12 N4 171.6(17) . . . . ? C10 C11 C12 N4 -144.6(13) . . . . ? C20 C15 C16 C17 -0.3(5) . . . . ? C21 C15 C16 C17 -179.2(3) . . . . ? C15 C16 C17 C18 2.3(5) . . . . ? C15 C16 C17 C22 -176.0(3) . . . . ? C16 C17 C18 C19 -2.4(5) . . . . ? C22 C17 C18 C19 176.0(3) . . . . ? C17 C18 C19 O5 179.9(3) . . . . ? C17 C18 C19 C20 0.4(5) . . . . ? O5 C19 C20 C15 -177.9(3) . . . . ? C18 C19 C20 C15 1.6(5) . . . . ? C16 C15 C20 C19 -1.6(5) . . . . ? C21 C15 C20 C19 177.3(3) . . . . ? C20 C15 C21 O1 2.6(5) . . . . ? C16 C15 C21 O1 -178.5(3) . . . . ? C20 C15 C21 O2 -175.0(3) . . . . ? C16 C15 C21 O2 3.9(5) . . . . ? C16 C17 C22 O4 -173.8(3) . . . . ? C18 C17 C22 O4 7.9(5) . . . . ? C16 C17 C22 O3 7.7(5) . . . . ? C18 C17 C22 O3 -170.6(3) . . . . ? O2 C21 O1 Cd1 -3.3(4) . . . . ? C15 C21 O1 Cd1 179.1(3) . . . . ? N1 Cd1 O1 C21 -92.9(2) . . . . ? N6 Cd1 O1 C21 82.2(2) 1_544 . . . ? O4 Cd1 O1 C21 169.5(2) 1_655 . . . ? O1W Cd1 O1 C21 -8.0(3) . . . . ? O2 Cd1 O1 C21 1.77(19) . . . . ? O3 Cd1 O1 C21 178.50(19) 1_655 . . . ? O1 C21 O2 Cd1 3.1(3) . . . . ? C15 C21 O2 Cd1 -179.4(3) . . . . ? N1 Cd1 O2 C21 86.2(2) . . . . ? N6 Cd1 O2 C21 -107.6(2) 1_544 . . . ? O4 Cd1 O2 C21 -18.7(3) 1_655 . . . ? O1W Cd1 O2 C21 171.1(2) . . . . ? O1 Cd1 O2 C21 -1.73(19) . . . . ? O3 Cd1 O2 C21 -163.0(6) 1_655 . . . ? O4 C22 O3 Cd1 -1.4(3) . . . 1_455 ? C17 C22 O3 Cd1 177.1(3) . . . 1_455 ? O3 C22 O4 Cd1 1.6(4) . . . 1_455 ? C17 C22 O4 Cd1 -176.9(3) . . . 1_455 ? N3 C1 N1 C2 -1.0(4) . . . . ? N3 C1 N1 Cd1 176.6(2) . . . . ? N2 C2 N1 C1 0.6(5) . . . . ? N2 C2 N1 Cd1 -176.8(3) . . . . ? N6 Cd1 N1 C1 144.1(4) 1_544 . . . ? O4 Cd1 N1 C1 26.4(3) 1_655 . . . ? O1W Cd1 N1 C1 170.7(3) . . . . ? O1 Cd1 N1 C1 -55.3(3) . . . . ? O2 Cd1 N1 C1 -108.7(3) . . . . ? O3 Cd1 N1 C1 78.2(3) 1_655 . . . ? N6 Cd1 N1 C2 -39.1(6) 1_544 . . . ? O4 Cd1 N1 C2 -156.8(4) 1_655 . . . ? O1W Cd1 N1 C2 -12.5(4) . . . . ? O1 Cd1 N1 C2 121.5(4) . . . . ? O2 Cd1 N1 C2 68.1(4) . . . . ? O3 Cd1 N1 C2 -105.0(4) 1_655 . . . ? N1 C2 N2 N3 0.1(6) . . . . ? N1 C1 N3 N2 1.1(5) . . . . ? N1 C1 N3 C3 176.9(4) . . . . ? C2 N2 N3 C1 -0.7(5) . . . . ? C2 N2 N3 C3 -176.8(4) . . . . ? C4 C3 N3 C1 -98.2(6) . . . . ? C4 C3 N3 N2 77.1(6) . . . . ? N6 C13 N4 N4' -109.6(17) . . . . ? N4' C13 N4 N5 99(2) . . . . ? N6 C13 N4 N5 -10.9(14) . . . . ? N4' C13 N4 N5' 67.4(16) . . . . ? N6 C13 N4 N5' -42.2(12) . . . . ? N4' C13 N4 C12 -47.0(16) . . . . ? N6 C13 N4 C12 -156.6(6) . . . . ? C11' C12 N4 N4' 158(2) . . . . ? C11 C12 N4 N4' -169(2) . . . . ? C11' C12 N4 N5 63(2) . . . . ? C11 C12 N4 N5 96.2(19) . . . . ? N4' C12 N4 N5 -95(2) . . . . ? C11' C12 N4 C13 -157.4(14) . . . . ? C11 C12 N4 C13 -124.6(13) . . . . ? N4' C12 N4 C13 44.5(16) . . . . ? C11' C12 N4 N5' 96.6(17) . . . . ? C11 C12 N4 N5' 129.3(16) . . . . ? N4' C12 N4 N5' -61.5(16) . . . . ? N5 N4 N4' C13 -105.8(12) . . . . ? N5' N4 N4' C13 -108.0(9) . . . . ? C12 N4 N4' C13 131.2(9) . . . . ? N5 N4 N4' N5' 2.2(14) . . . . ? C13 N4 N4' N5' 108.0(9) . . . . ? C12 N4 N4' N5' -120.9(9) . . . . ? N5 N4 N4' C12 123.1(11) . . . . ? C13 N4 N4' C12 -131.2(9) . . . . ? N5' N4 N4' C12 120.9(9) . . . . ? C13 N4 N4' N5 105.8(12) . . . . ? N5' N4 N4' N5 -2.2(14) . . . . ? C12 N4 N4' N5 -123.1(11) . . . . ? N6 C13 N4' N4 80.3(18) . . . . ? N6 C13 N4' N5' 3.0(12) . . . . ? N4 C13 N4' N5' -77.3(17) . . . . ? N6 C13 N4' C12 171.7(9) . . . . ? N4 C13 N4' C12 91(2) . . . . ? N6 C13 N4' N5 32.7(10) . . . . ? N4 C13 N4' N5 -47.6(15) . . . . ? C11' C12 N4' N4 -22(2) . . . . ? C11 C12 N4' N4 12(2) . . . . ? C11' C12 N4' C13 -113.0(16) . . . . ? C11 C12 N4' C13 -79.2(18) . . . . ? N4 C12 N4' C13 -91(2) . . . . ? C11' C12 N4' N5' 54.6(18) . . . . ? C11 C12 N4' N5' 88.4(17) . . . . ? N4 C12 N4' N5' 76.6(19) . . . . ? C11' C12 N4' N5 22.0(17) . . . . ? C11 C12 N4' N5 55.8(17) . . . . ? N4 C12 N4' N5 44.0(16) . . . . ? N4' N4 N5 N5' -4(3) . . . . ? C13 N4 N5 N5' -69.4(19) . . . . ? C12 N4 N5 N5' 69(2) . . . . ? N4' N4 N5 C14 67(2) . . . . ? C13 N4 N5 C14 1.6(17) . . . . ? N5' N4 N5 C14 71.0(16) . . . . ? C12 N4 N5 C14 140.1(11) . . . . ? C13 N4 N5 N4' -65.5(18) . . . . ? N5' N4 N5 N4' 4(3) . . . . ? C12 N4 N5 N4' 73(2) . . . . ? N6 C14 N5 N5' 88.1(19) . . . . ? N6 C14 N5 N4 8.4(16) . . . . ? N5' C14 N5 N4 -79.7(18) . . . . ? N6 C14 N5 N4' 30.2(12) . . . . ? N5' C14 N5 N4' -57.9(15) . . . . ? N4 N4' N5 N5' 176(3) . . . . ? C13 N4' N5 N5' -104.9(19) . . . . ? C12 N4' N5 N5' 108.0(19) . . . . ? C13 N4' N5 N4 79(2) . . . . ? N5' N4' N5 N4 -176(3) . . . . ? C12 N4' N5 N4 -67.5(18) . . . . ? N4 N4' N5 C14 -116(2) . . . . ? C13 N4' N5 C14 -36.3(11) . . . . ? N5' N4' N5 C14 68.6(17) . . . . ? C12 N4' N5 C14 176.7(9) . . . . ? N4 N5 N5' C14 105.1(7) . . . . ? N4' N5 N5' C14 103.3(9) . . . . ? N4 N5 N5' N4' 1.8(12) . . . . ? C14 N5 N5' N4' -103.3(9) . . . . ? C14 N5 N5' N4 -105.1(7) . . . . ? N4' N5 N5' N4 -1.8(12) . . . . ? N6 C14 N5' N5 -105.4(17) . . . . ? N6 C14 N5' N4' -19.0(13) . . . . ? N5 C14 N5' N4' 86.4(17) . . . . ? N6 C14 N5' N4 -46.1(13) . . . . ? N5 C14 N5' N4 59.3(14) . . . . ? N4 N4' N5' N5 -3(2) . . . . ? C13 N4' N5' N5 82.8(18) . . . . ? C12 N4' N5' N5 -87.4(19) . . . . ? N4 N4' N5' C14 -76.2(18) . . . . ? C13 N4' N5' C14 9.9(14) . . . . ? C12 N4' N5' C14 -160.3(9) . . . . ? N5 N4' N5' C14 -72.8(17) . . . . ? C13 N4' N5' N4 86.2(18) . . . . ? C12 N4' N5' N4 -84.0(17) . . . . ? N5 N4' N5' N4 3(2) . . . . ? N4' N4 N5' N5 176(2) . . . . ? C13 N4 N5' N5 118.8(17) . . . . ? C12 N4 N5' N5 -127.2(18) . . . . ? N4' N4 N5' C14 108.1(18) . . . . ? N5 N4 N5' C14 -68.1(15) . . . . ? C13 N4 N5' C14 50.7(13) . . . . ? C12 N4 N5' C14 164.7(9) . . . . ? N5 N4 N5' N4' -176(2) . . . . ? C13 N4 N5' N4' -57.4(16) . . . . ? C12 N4 N5' N4' 56.7(16) . . . . ? N4' C13 N6 C14 -14.6(8) . . . . ? N4 C13 N6 C14 14.6(8) . . . . ? N4' C13 N6 Cd1 175.9(6) . . . 1_566 ? N4 C13 N6 Cd1 -154.8(6) . . . 1_566 ? N5' C14 N6 C13 20.8(10) . . . . ? N5 C14 N6 C13 -15.2(11) . . . . ? N5' C14 N6 Cd1 -170.3(7) . . . 1_566 ? N5 C14 N6 Cd1 153.7(8) . . . 1_566 ? _diffrn_measured_fraction_theta_max 0.840 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.606 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 961131' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_comp7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C74 H90 Cd4 N18 O17' _chemical_formula_weight 1953.24 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 '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' _symmetry_space_group_name_hall '-p 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1865(10) _cell_length_b 13.716(2) _cell_length_c 15.936(2) _cell_angle_alpha 111.617(13) _cell_angle_beta 93.704(9) _cell_angle_gamma 95.474(10) _cell_volume 2048.6(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7433 _cell_measurement_theta_min 4.2 _cell_measurement_theta_max 25.4 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 988 _exptl_absorpt_coefficient_mu 1.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.792 _exptl_absorpt_correction_T_max 0.852 _exptl_absorpt_process_details ? _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13565 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.1285 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.16 _diffrn_reflns_theta_max 25.35 _reflns_number_total 7433 _reflns_number_gt 3775 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 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^)+(0.0260P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7433 _refine_ls_number_parameters 504 _refine_ls_number_restraints 40 _refine_ls_R_factor_all 0.1002 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0657 _refine_ls_goodness_of_fit_ref 0.781 _refine_ls_restrained_S_all 0.862 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.34801(3) 0.38098(3) 0.94099(3) 0.04262(14) Uani 1 1 d . . . Cd2 Cd 0.00488(4) 0.18441(3) 0.89941(3) 0.04963(15) Uani 1 1 d . . . C1 C 0.2712(5) 0.1193(5) 0.8883(4) 0.0522(15) Uani 1 1 d . . . C2 C 0.3829(5) 0.0564(4) 0.8853(4) 0.0424(14) Uani 1 1 d . . . C3 C 0.3615(5) -0.0417(4) 0.8910(4) 0.0505(16) Uani 1 1 d . . . H3 H 0.2763 -0.0683 0.8963 0.061 Uiso 1 1 calc R . . C4 C 0.4641(5) -0.1010(4) 0.8888(4) 0.0517(16) Uani 1 1 d . . . H4 H 0.4481 -0.1671 0.8925 0.062 Uiso 1 1 calc R . . C5 C 0.5910(5) -0.0615(4) 0.8812(4) 0.0541(16) Uani 1 1 d . . . H5 H 0.6601 -0.1020 0.8783 0.065 Uiso 1 1 calc R . . C6 C 0.6156(5) 0.0384(4) 0.8780(4) 0.0399(13) Uani 1 1 d . . . C7 C 0.5109(4) 0.0964(4) 0.8795(4) 0.0414(13) Uani 1 1 d . . . H7 H 0.5267 0.1629 0.8765 0.050 Uiso 1 1 calc R . . C8 C 0.7545(5) 0.0849(5) 0.8786(4) 0.0478(15) Uani 1 1 d . . . C9 C 0.6027(5) 0.4005(4) 0.8850(5) 0.0437(15) Uani 1 1 d . . . C10 C 0.7256(4) 0.4039(4) 0.8376(4) 0.0333(12) Uani 1 1 d . . . C11 C 0.8480(4) 0.4051(4) 0.8805(3) 0.0365(13) Uani 1 1 d . . . H11 H 0.8540 0.4015 0.9378 0.044 Uiso 1 1 calc R . . C12 C 0.9621(4) 0.4116(4) 0.8391(4) 0.0367(13) Uani 1 1 d . . . C13 C 0.9526(5) 0.4227(4) 0.7571(4) 0.0531(16) Uani 1 1 d . . . H13 H 1.0294 0.4315 0.7307 0.064 Uiso 1 1 calc R . . C14 C 0.8301(6) 0.4209(5) 0.7126(4) 0.0638(18) Uani 1 1 d . . . H14 H 0.8244 0.4270 0.6563 0.077 Uiso 1 1 calc R . . C15 C 0.7186(5) 0.4102(4) 0.7525(4) 0.0507(15) Uani 1 1 d . . . H15 H 0.6361 0.4070 0.7223 0.061 Uiso 1 1 calc R . . C16 C 1.0944(5) 0.4052(4) 0.8837(4) 0.0443(14) Uani 1 1 d . . . N2 N 0.3762(6) 0.3409(4) 1.2059(4) 0.0676(15) Uani 1 1 d . . . C18 C 0.5155(5) 0.3836(4) 1.1223(4) 0.0466(15) Uani 1 1 d . . . H18 H 0.5942 0.4051 1.1039 0.056 Uiso 1 1 calc R . . C19 C 0.6090(7) 0.3840(5) 1.2714(4) 0.0708(19) Uani 1 1 d . . . H19A H 0.6945 0.3979 1.2517 0.085 Uiso 1 1 calc R . . H19B H 0.6072 0.3186 1.2818 0.085 Uiso 1 1 calc R . . C20 C 0.5940(8) 0.4702(7) 1.3564(6) 0.109(3) Uani 1 1 d . . . H20A H 0.5033 0.4632 1.3707 0.131 Uiso 1 1 calc R . . H20B H 0.6117 0.5372 1.3491 0.131 Uiso 1 1 calc R . . C21 C 0.6901(8) 0.4697(8) 1.4359(5) 0.110(3) Uani 1 1 d . . . H21A H 0.6691 0.5216 1.4922 0.132 Uiso 1 1 calc R . . H21B H 0.6759 0.4008 1.4402 0.132 Uiso 1 1 calc R . . C22 C 0.8343(7) 0.4939(6) 1.4257(5) 0.089(2) Uani 1 1 d . . . H22A H 0.8499 0.5639 1.4238 0.107 Uiso 1 1 calc R . . H22B H 0.8553 0.4434 1.3686 0.107 Uiso 1 1 calc R . . C23 C 0.9279(6) 0.4888(6) 1.5056(5) 0.084(2) Uani 1 1 d . . . H23A H 0.9079 0.5401 1.5626 0.100 Uiso 1 1 calc R . . H23B H 0.9113 0.4191 1.5081 0.100 Uiso 1 1 calc R . . C24 C 0.0085(5) 0.1612(5) 1.0970(5) 0.0565(17) Uani 1 1 d . . . H24 H 0.0495 0.1003 1.0746 0.068 Uiso 1 1 calc R . . C25 C -0.0775(7) 0.2973(5) 1.1107(6) 0.076(2) Uani 1 1 d U . . H25 H -0.1079 0.3522 1.0972 0.091 Uiso 1 1 calc R . . C26 C -0.0188(8) 0.1598(6) 1.2514(5) 0.088(2) Uani 1 1 d . . . H26A H -0.0219 0.0835 1.2265 0.106 Uiso 1 1 calc R . . H26B H -0.0918 0.1775 1.2882 0.106 Uiso 1 1 calc R . . C27 C 0.1173(11) 0.2117(8) 1.3124(7) 0.134(4) Uani 1 1 d . . . H27A H 0.1894 0.1966 1.2745 0.161 Uiso 1 1 calc R . . H27B H 0.1183 0.2878 1.3385 0.161 Uiso 1 1 calc R . . C28 C 0.1384(15) 0.1757(13) 1.3809(9) 0.218(7) Uani 1 1 d D . . H28A H 0.1246 0.0990 1.3542 0.261 Uiso 1 1 calc R . . H28B H 0.0702 0.1977 1.4213 0.261 Uiso 1 1 calc R . . C29 C 0.2748(18) 0.2097(14) 1.4404(13) 0.239(7) Uani 1 1 d DU . . H29A H 0.2957 0.2861 1.4649 0.287 Uiso 1 1 calc R . . H29B H 0.2728 0.1857 1.4905 0.287 Uiso 1 1 calc R . . C30 C 0.369(2) 0.163(2) 1.3843(12) 0.356(15) Uani 1 1 d D . . H30A H 0.3326 0.0924 1.3436 0.427 Uiso 1 1 calc R . . H30B H 0.3926 0.2043 1.3479 0.427 Uiso 1 1 calc R . . C31 C 0.577(2) 0.1249(18) 1.3928(18) 0.345(14) Uiso 1 1 d D . . H31A H 0.6013 0.1814 1.3717 0.414 Uiso 1 1 calc RD . . H31B H 0.5300 0.0684 1.3396 0.414 Uiso 1 1 calc RD . . C32 C 0.479(3) 0.160(2) 1.436(2) 0.360(13) Uani 1 1 d DU . . H32A H 0.5089 0.2304 1.4802 0.433 Uiso 1 1 calc R . . H32B H 0.4545 0.1154 1.4694 0.433 Uiso 1 1 calc R . . C33 C 0.6982(18) 0.0872(14) 1.3957(8) 0.251(8) Uani 1 1 d D . . H33A H 0.7653 0.1376 1.3881 0.301 Uiso 1 1 calc RD . . H33B H 0.6945 0.0217 1.3434 0.301 Uiso 1 1 calc RD . . C34 C 0.745(2) 0.0665(17) 1.4789(15) 0.314(11) Uani 1 1 d DU . . H34A H 0.6708 0.0534 1.5100 0.377 Uiso 1 1 calc R . . H34B H 0.7942 0.0061 1.4625 0.377 Uiso 1 1 calc R . . C35 C 0.8247(17) 0.1564(16) 1.5317(9) 0.266(9) Uani 1 1 d D . . H35A H 0.7712 0.2132 1.5560 0.320 Uiso 1 1 calc R . . H35B H 0.8865 0.1766 1.4953 0.320 Uiso 1 1 calc RD . . C36 C 0.8863(10) 0.1464(7) 1.6973(7) 0.099(3) Uani 1 1 d . . . H36 H 0.8022 0.1428 1.7163 0.119 Uiso 1 1 calc R . . C37 C 1.0904(10) 0.1626(7) 1.6941(7) 0.112(3) Uani 1 1 d . . . H37 H 1.1808 0.1717 1.7122 0.134 Uiso 1 1 calc R . . N1 N 0.3979(4) 0.3612(3) 1.0740(3) 0.0462(12) Uani 1 1 d . . . C17 C 0.3177(6) 0.3353(5) 1.1295(5) 0.0604(17) Uani 1 1 d . . . H17 H 0.2269 0.3149 1.1137 0.072 Uiso 1 1 calc R . . N3 N 0.5055(5) 0.3713(4) 1.2001(4) 0.0557(13) Uani 1 1 d . . . N4 N -0.0165(4) 0.2215(4) 1.0518(4) 0.0585(14) Uani 1 1 d . . . N5 N -0.0900(6) 0.2870(4) 1.1882(4) 0.0789(17) Uani 1 1 d . . . N6 N -0.0322(5) 0.1984(4) 1.1778(4) 0.0630(14) Uani 1 1 d . . . N7 N 0.9093(11) 0.1378(8) 1.6175(7) 0.152(4) Uani 1 1 d D . . N8 N 1.0409(13) 0.1503(8) 1.6123(7) 0.158(4) Uani 1 1 d . . . N9 N 0.9967(6) 0.1608(4) 1.7484(4) 0.0675(15) Uani 1 1 d . . . O1 O 0.1623(4) 0.0848(3) 0.9060(3) 0.0766(13) Uani 1 1 d . . . O2 O 0.2884(4) 0.2016(3) 0.8712(3) 0.0639(12) Uani 1 1 d . . . O3 O 0.7732(3) 0.1787(3) 0.8810(3) 0.0657(12) Uani 1 1 d . . . O4 O 0.8475(3) 0.0305(3) 0.8759(3) 0.0637(12) Uani 1 1 d . . . O5 O 0.6115(3) 0.4325(3) 0.9692(3) 0.0497(10) Uani 1 1 d . . . O6 O 0.4920(3) 0.3646(3) 0.8350(3) 0.0599(11) Uani 1 1 d . . . O7 O 1.0974(3) 0.3625(3) 0.9428(3) 0.0455(9) Uani 1 1 d . . . O8 O 1.1983(3) 0.4380(3) 0.8600(3) 0.0574(11) Uani 1 1 d . . . O1W O 0.4904(16) -0.1690(12) 1.3153(11) 0.179(6) Uiso 0.50 1 d P . . 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 Cd1 0.0259(2) 0.0410(3) 0.0602(3) 0.0182(2) 0.0038(2) 0.00485(19) Cd2 0.0267(2) 0.0461(3) 0.0802(4) 0.0279(3) 0.0112(2) 0.0036(2) C1 0.033(3) 0.050(4) 0.064(4) 0.011(4) 0.001(3) 0.006(3) C2 0.031(3) 0.033(3) 0.058(4) 0.010(3) 0.007(3) 0.007(2) C3 0.027(3) 0.041(3) 0.078(5) 0.016(3) 0.015(3) 0.000(3) C4 0.043(3) 0.027(3) 0.081(5) 0.018(3) 0.006(3) -0.003(3) C5 0.035(3) 0.035(3) 0.093(5) 0.023(3) 0.009(3) 0.015(3) C6 0.028(3) 0.033(3) 0.058(4) 0.016(3) 0.006(3) 0.005(2) C7 0.026(3) 0.035(3) 0.065(4) 0.022(3) 0.002(3) 0.006(2) C8 0.033(3) 0.041(4) 0.072(4) 0.024(3) 0.013(3) 0.005(3) C9 0.029(3) 0.036(3) 0.072(5) 0.024(4) 0.010(3) 0.008(3) C10 0.023(3) 0.031(3) 0.048(4) 0.017(3) 0.003(2) 0.007(2) C11 0.037(3) 0.037(3) 0.043(3) 0.020(3) 0.009(3) 0.014(2) C12 0.024(3) 0.038(3) 0.050(4) 0.017(3) 0.007(2) 0.008(2) C13 0.035(3) 0.075(4) 0.065(4) 0.041(4) 0.022(3) 0.012(3) C14 0.051(4) 0.097(5) 0.065(5) 0.052(4) 0.012(3) 0.020(4) C15 0.037(3) 0.064(4) 0.059(4) 0.032(4) 0.000(3) 0.015(3) C16 0.029(3) 0.038(3) 0.059(4) 0.009(3) 0.005(3) 0.007(3) N2 0.063(4) 0.071(4) 0.083(4) 0.045(4) 0.018(3) 0.008(3) C18 0.037(3) 0.051(4) 0.061(4) 0.031(3) 0.008(3) 0.010(3) C19 0.079(5) 0.081(5) 0.053(5) 0.019(4) 0.008(4) 0.035(4) C20 0.092(6) 0.128(8) 0.086(6) 0.017(6) -0.010(5) 0.018(5) C21 0.102(7) 0.142(8) 0.075(6) 0.026(6) 0.020(5) 0.013(6) C22 0.096(6) 0.099(6) 0.061(5) 0.021(5) 0.001(4) -0.003(5) C23 0.089(5) 0.101(6) 0.066(5) 0.039(4) 0.009(4) 0.009(5) C24 0.043(3) 0.045(4) 0.076(5) 0.016(4) 0.014(3) 0.005(3) C25 0.076(4) 0.064(4) 0.104(6) 0.045(4) 0.025(4) 0.022(4) C26 0.097(6) 0.094(6) 0.084(6) 0.041(5) 0.020(5) 0.026(5) C27 0.170(11) 0.152(9) 0.101(8) 0.075(7) -0.002(7) 0.019(8) C28 0.246(17) 0.246(16) 0.123(10) 0.057(11) -0.048(11) -0.052(13) C29 0.239(7) 0.239(7) 0.239(7) 0.090(3) 0.0257(14) 0.0307(15) C30 0.191(17) 0.68(5) 0.164(15) 0.11(2) 0.009(14) 0.11(2) C32 0.360(17) 0.388(16) 0.345(16) 0.151(11) 0.043(11) 0.045(11) C33 0.30(2) 0.36(2) 0.088(9) 0.079(12) -0.042(11) 0.071(18) C34 0.314(11) 0.314(11) 0.314(11) 0.118(4) 0.0341(16) 0.0404(18) C35 0.246(19) 0.32(2) 0.155(14) 0.005(15) 0.029(14) 0.013(18) C36 0.107(8) 0.107(7) 0.075(7) 0.032(6) -0.006(6) -0.006(5) C37 0.112(7) 0.148(8) 0.070(7) 0.026(6) 0.024(6) 0.047(6) N1 0.037(3) 0.037(3) 0.069(3) 0.025(3) 0.008(3) 0.000(2) C17 0.042(4) 0.053(4) 0.092(6) 0.036(4) 0.008(4) -0.006(3) N3 0.047(3) 0.056(3) 0.071(4) 0.032(3) 0.002(3) 0.011(2) N4 0.039(3) 0.052(3) 0.091(4) 0.031(3) 0.023(3) 0.009(2) N5 0.089(4) 0.063(4) 0.086(5) 0.021(4) 0.029(4) 0.029(3) N6 0.053(3) 0.059(4) 0.080(4) 0.028(3) 0.013(3) 0.009(3) N7 0.144(8) 0.220(10) 0.081(7) 0.048(7) -0.019(7) 0.025(8) N8 0.190(10) 0.207(10) 0.067(7) 0.026(6) 0.046(7) 0.063(9) N9 0.073(4) 0.053(3) 0.066(4) 0.012(3) 0.009(4) 0.004(3) O1 0.031(2) 0.092(3) 0.123(4) 0.053(3) 0.025(2) 0.022(2) O2 0.044(2) 0.036(2) 0.103(4) 0.018(3) -0.004(2) 0.0099(19) O3 0.029(2) 0.052(3) 0.130(4) 0.051(3) 0.014(2) 0.0009(18) O4 0.0267(19) 0.049(2) 0.117(4) 0.029(3) 0.017(2) 0.0143(18) O5 0.047(2) 0.046(2) 0.063(3) 0.024(2) 0.026(2) 0.0178(19) O6 0.028(2) 0.070(3) 0.074(3) 0.019(2) 0.006(2) 0.0039(19) O7 0.036(2) 0.041(2) 0.062(3) 0.021(2) -0.0025(19) 0.0115(17) O8 0.0227(19) 0.073(3) 0.079(3) 0.032(2) 0.007(2) 0.0026(19) _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 Cd1 N1 2.266(5) . ? Cd1 O6 2.272(3) . ? Cd1 O2 2.296(4) . ? Cd1 O8 2.306(4) 1_455 ? Cd1 O5 2.406(4) 2_667 ? Cd1 O7 2.545(3) 1_455 ? Cd2 O1 2.225(4) . ? Cd2 N9 2.302(6) 1_454 ? Cd2 N4 2.320(5) . ? Cd2 O3 2.349(3) 1_455 ? Cd2 O7 2.359(4) 1_455 ? Cd2 O4 2.421(4) 1_455 ? Cd2 C8 2.715(5) 1_455 ? C1 O1 1.254(6) . ? C1 O2 1.255(6) . ? C1 C2 1.484(7) . ? C2 C3 1.379(7) . ? C2 C7 1.388(6) . ? C3 C4 1.380(7) . ? C3 H3 0.9300 . ? C4 C5 1.383(7) . ? C4 H4 0.9300 . ? C5 C6 1.390(7) . ? C5 H5 0.9300 . ? C6 C7 1.387(6) . ? C6 C8 1.494(7) . ? C7 H7 0.9300 . ? C8 O4 1.254(6) . ? C8 O3 1.269(6) . ? C8 Cd2 2.715(5) 1_655 ? C9 O5 1.244(6) . ? C9 O6 1.279(6) . ? C9 C10 1.510(7) . ? C10 C11 1.379(6) . ? C10 C15 1.387(7) . ? C11 C12 1.385(6) . ? C11 H11 0.9300 . ? C12 C13 1.368(7) . ? C12 C16 1.508(7) . ? C13 C14 1.389(7) . ? C13 H13 0.9300 . ? C14 C15 1.359(7) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 O8 1.246(6) . ? C16 O7 1.280(6) . ? N2 C17 1.294(8) . ? N2 N3 1.363(6) . ? C18 N3 1.320(7) . ? C18 N1 1.326(7) . ? C18 H18 0.9300 . ? C19 N3 1.447(7) . ? C19 C20 1.463(9) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.553(10) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.508(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.568(9) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C23 1.508(12) 2_768 ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 N6 1.310(7) . ? C24 N4 1.312(7) . ? C24 H24 0.9300 . ? C25 N5 1.308(8) . ? C25 N4 1.352(8) . ? C25 H25 0.9300 . ? C26 N6 1.458(8) . ? C26 C27 1.582(12) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.367(13) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.558(16) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.389(16) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C32 1.37(2) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.27(2) . ? C31 C33 1.388(13) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.513(19) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.357(16) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 N7 1.680(17) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 N7 1.273(10) . ? C36 N9 1.299(9) . ? C36 H36 0.9300 . ? C37 N8 1.312(11) . ? C37 N9 1.334(9) . ? C37 H37 0.9300 . ? N1 C17 1.359(7) . ? C17 H17 0.9300 . ? N5 N6 1.361(7) . ? N7 N8 1.347(11) . ? N9 Cd2 2.302(6) 1_656 ? O3 Cd2 2.349(3) 1_655 ? O4 Cd2 2.421(4) 1_655 ? O5 Cd1 2.406(4) 2_667 ? O7 Cd2 2.359(4) 1_655 ? O7 Cd1 2.545(3) 1_655 ? O8 Cd1 2.306(4) 1_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cd1 O6 123.82(14) . . ? N1 Cd1 O2 89.59(15) . . ? O6 Cd1 O2 86.87(15) . . ? N1 Cd1 O8 145.16(14) . 1_455 ? O6 Cd1 O8 90.39(13) . 1_455 ? O2 Cd1 O8 99.63(14) . 1_455 ? N1 Cd1 O5 85.00(15) . 2_667 ? O6 Cd1 O5 101.77(13) . 2_667 ? O2 Cd1 O5 171.34(14) . 2_667 ? O8 Cd1 O5 81.23(14) 1_455 2_667 ? N1 Cd1 O7 96.67(14) . 1_455 ? O6 Cd1 O7 136.51(13) . 1_455 ? O2 Cd1 O7 77.45(12) . 1_455 ? O8 Cd1 O7 53.75(12) 1_455 1_455 ? O5 Cd1 O7 96.43(11) 2_667 1_455 ? O1 Cd2 N9 99.62(19) . 1_454 ? O1 Cd2 N4 89.35(17) . . ? N9 Cd2 N4 170.94(19) 1_454 . ? O1 Cd2 O3 141.68(14) . 1_455 ? N9 Cd2 O3 85.94(19) 1_454 1_455 ? N4 Cd2 O3 86.17(16) . 1_455 ? O1 Cd2 O7 110.38(14) . 1_455 ? N9 Cd2 O7 90.95(16) 1_454 1_455 ? N4 Cd2 O7 87.16(15) . 1_455 ? O3 Cd2 O7 107.38(12) 1_455 1_455 ? O1 Cd2 O4 86.47(14) . 1_455 ? N9 Cd2 O4 95.29(17) 1_454 1_455 ? N4 Cd2 O4 83.84(15) . 1_455 ? O3 Cd2 O4 55.21(12) 1_455 1_455 ? O7 Cd2 O4 160.82(11) 1_455 1_455 ? O1 Cd2 C8 113.87(16) . 1_455 ? N9 Cd2 C8 92.6(2) 1_454 1_455 ? N4 Cd2 C8 82.42(17) . 1_455 ? O3 Cd2 C8 27.83(13) 1_455 1_455 ? O7 Cd2 C8 134.27(14) 1_455 1_455 ? O4 Cd2 C8 27.50(13) 1_455 1_455 ? O1 C1 O2 123.3(5) . . ? O1 C1 C2 117.2(6) . . ? O2 C1 C2 119.5(5) . . ? C3 C2 C7 118.9(4) . . ? C3 C2 C1 120.3(5) . . ? C7 C2 C1 120.8(5) . . ? C2 C3 C4 121.2(5) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 119.7(5) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 120.2(5) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 119.3(4) . . ? C7 C6 C8 120.6(5) . . ? C5 C6 C8 120.0(4) . . ? C6 C7 C2 120.8(5) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? O4 C8 O3 122.5(5) . . ? O4 C8 C6 119.6(5) . . ? O3 C8 C6 117.9(5) . . ? O4 C8 Cd2 63.1(3) . 1_655 ? O3 C8 Cd2 59.8(3) . 1_655 ? C6 C8 Cd2 173.5(4) . 1_655 ? O5 C9 O6 122.8(5) . . ? O5 C9 C10 120.0(5) . . ? O6 C9 C10 117.2(6) . . ? C11 C10 C15 119.0(4) . . ? C11 C10 C9 119.8(5) . . ? C15 C10 C9 121.1(5) . . ? C10 C11 C12 120.5(5) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 119.1(5) . . ? C13 C12 C16 120.8(5) . . ? C11 C12 C16 120.0(5) . . ? C12 C13 C14 121.0(5) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 119.0(5) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C10 121.2(5) . . ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.4 . . ? O8 C16 O7 121.4(5) . . ? O8 C16 C12 119.4(5) . . ? O7 C16 C12 119.1(5) . . ? C17 N2 N3 102.7(5) . . ? N3 C18 N1 110.8(5) . . ? N3 C18 H18 124.6 . . ? N1 C18 H18 124.6 . . ? N3 C19 C20 112.3(5) . . ? N3 C19 H19A 109.1 . . ? C20 C19 H19A 109.1 . . ? N3 C19 H19B 109.1 . . ? C20 C19 H19B 109.1 . . ? H19A C19 H19B 107.9 . . ? C19 C20 C21 111.4(7) . . ? C19 C20 H20A 109.4 . . ? C21 C20 H20A 109.4 . . ? C19 C20 H20B 109.4 . . ? C21 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? C22 C21 C20 113.5(6) . . ? C22 C21 H21A 108.9 . . ? C20 C21 H21A 108.9 . . ? C22 C21 H21B 108.9 . . ? C20 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C21 C22 C23 111.8(6) . . ? C21 C22 H22A 109.3 . . ? C23 C22 H22A 109.3 . . ? C21 C22 H22B 109.3 . . ? C23 C22 H22B 109.3 . . ? H22A C22 H22B 107.9 . . ? C23 C23 C22 111.7(7) 2_768 . ? C23 C23 H23A 109.3 2_768 . ? C22 C23 H23A 109.3 . . ? C23 C23 H23B 109.3 2_768 . ? C22 C23 H23B 109.3 . . ? H23A C23 H23B 107.9 . . ? N6 C24 N4 110.8(5) . . ? N6 C24 H24 124.6 . . ? N4 C24 H24 124.6 . . ? N5 C25 N4 114.4(6) . . ? N5 C25 H25 122.8 . . ? N4 C25 H25 122.8 . . ? N6 C26 C27 109.8(6) . . ? N6 C26 H26A 109.7 . . ? C27 C26 H26A 109.7 . . ? N6 C26 H26B 109.7 . . ? C27 C26 H26B 109.7 . . ? H26A C26 H26B 108.2 . . ? C28 C27 C26 112.8(10) . . ? C28 C27 H27A 109.0 . . ? C26 C27 H27A 109.0 . . ? C28 C27 H27B 109.0 . . ? C26 C27 H27B 109.0 . . ? H27A C27 H27B 107.8 . . ? C27 C28 C29 119.0(14) . . ? C27 C28 H28A 107.6 . . ? C29 C28 H28A 107.6 . . ? C27 C28 H28B 107.6 . . ? C29 C28 H28B 107.6 . . ? H28A C28 H28B 107.0 . . ? C30 C29 C28 106.9(16) . . ? C30 C29 H29A 110.3 . . ? C28 C29 H29A 110.3 . . ? C30 C29 H29B 110.3 . . ? C28 C29 H29B 110.3 . . ? H29A C29 H29B 108.6 . . ? C32 C30 C29 109.6(17) . . ? C32 C30 H30A 109.8 . . ? C29 C30 H30A 109.8 . . ? C32 C30 H30B 109.8 . . ? C29 C30 H30B 109.8 . . ? H30A C30 H30B 108.2 . . ? C32 C31 C33 147(3) . . ? C32 C31 H31A 100.2 . . ? C33 C31 H31A 100.2 . . ? C32 C31 H31B 100.2 . . ? C33 C31 H31B 100.2 . . ? H31A C31 H31B 104.2 . . ? C31 C32 C30 116(3) . . ? C31 C32 H32A 108.3 . . ? C30 C32 H32A 108.3 . . ? C31 C32 H32B 108.3 . . ? C30 C32 H32B 108.3 . . ? H32A C32 H32B 107.4 . . ? C31 C33 C34 119(2) . . ? C31 C33 H33A 107.7 . . ? C34 C33 H33A 107.7 . . ? C31 C33 H33B 107.7 . . ? C34 C33 H33B 107.7 . . ? H33A C33 H33B 107.1 . . ? C35 C34 C33 104.4(15) . . ? C35 C34 H34A 110.9 . . ? C33 C34 H34A 110.9 . . ? C35 C34 H34B 110.9 . . ? C33 C34 H34B 110.9 . . ? H34A C34 H34B 108.9 . . ? C34 C35 N7 110.4(17) . . ? C34 C35 H35A 109.6 . . ? N7 C35 H35A 109.6 . . ? C34 C35 H35B 109.6 . . ? N7 C35 H35B 109.6 . . ? H35A C35 H35B 108.1 . . ? N7 C36 N9 110.5(9) . . ? N7 C36 H36 124.8 . . ? N9 C36 H36 124.8 . . ? N8 C37 N9 112.5(9) . . ? N8 C37 H37 123.8 . . ? N9 C37 H37 123.8 . . ? C18 N1 C17 101.8(5) . . ? C18 N1 Cd1 127.3(4) . . ? C17 N1 Cd1 130.5(4) . . ? N2 C17 N1 115.4(5) . . ? N2 C17 H17 122.3 . . ? N1 C17 H17 122.3 . . ? C18 N3 N2 109.3(5) . . ? C18 N3 C19 129.1(5) . . ? N2 N3 C19 121.6(5) . . ? C24 N4 C25 102.8(5) . . ? C24 N4 Cd2 126.6(4) . . ? C25 N4 Cd2 129.6(5) . . ? C25 N5 N6 102.3(5) . . ? C24 N6 N5 109.7(5) . . ? C24 N6 C26 129.2(6) . . ? N5 N6 C26 121.0(6) . . ? C36 N7 N8 110.5(9) . . ? C36 N7 C35 134.6(12) . . ? N8 N7 C35 110.9(12) . . ? C37 N8 N7 102.4(8) . . ? C36 N9 C37 104.1(7) . . ? C36 N9 Cd2 123.0(6) . 1_656 ? C37 N9 Cd2 132.8(6) . 1_656 ? C1 O1 Cd2 111.8(4) . . ? C1 O2 Cd1 141.6(4) . . ? C8 O3 Cd2 92.3(3) . 1_655 ? C8 O4 Cd2 89.4(3) . 1_655 ? C9 O5 Cd1 120.1(3) . 2_667 ? C9 O6 Cd1 101.3(4) . . ? C16 O7 Cd2 119.0(3) . 1_655 ? C16 O7 Cd1 86.4(3) . 1_655 ? Cd2 O7 Cd1 111.88(13) 1_655 1_655 ? C16 O8 Cd1 98.3(3) . 1_655 ? 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 O1 C1 C2 C3 7.6(9) . . . . ? O2 C1 C2 C3 -170.7(5) . . . . ? O1 C1 C2 C7 -170.5(5) . . . . ? O2 C1 C2 C7 11.2(9) . . . . ? C7 C2 C3 C4 -1.4(9) . . . . ? C1 C2 C3 C4 -179.6(6) . . . . ? C2 C3 C4 C5 0.2(9) . . . . ? C3 C4 C5 C6 1.5(9) . . . . ? C4 C5 C6 C7 -2.0(9) . . . . ? C4 C5 C6 C8 174.2(6) . . . . ? C5 C6 C7 C2 0.8(8) . . . . ? C8 C6 C7 C2 -175.4(5) . . . . ? C3 C2 C7 C6 0.9(8) . . . . ? C1 C2 C7 C6 179.1(5) . . . . ? C7 C6 C8 O4 -178.9(5) . . . . ? C5 C6 C8 O4 4.9(9) . . . . ? C7 C6 C8 O3 0.3(8) . . . . ? C5 C6 C8 O3 -175.9(5) . . . . ? C7 C6 C8 Cd2 68(4) . . . 1_655 ? C5 C6 C8 Cd2 -108(3) . . . 1_655 ? O5 C9 C10 C11 23.4(7) . . . . ? O6 C9 C10 C11 -157.2(5) . . . . ? O5 C9 C10 C15 -154.1(5) . . . . ? O6 C9 C10 C15 25.4(7) . . . . ? C15 C10 C11 C12 -0.5(7) . . . . ? C9 C10 C11 C12 -178.0(4) . . . . ? C10 C11 C12 C13 3.5(7) . . . . ? C10 C11 C12 C16 -175.8(4) . . . . ? C11 C12 C13 C14 -4.0(8) . . . . ? C16 C12 C13 C14 175.3(5) . . . . ? C12 C13 C14 C15 1.4(9) . . . . ? C13 C14 C15 C10 1.8(9) . . . . ? C11 C10 C15 C14 -2.2(8) . . . . ? C9 C10 C15 C14 175.2(5) . . . . ? C13 C12 C16 O8 19.4(8) . . . . ? C11 C12 C16 O8 -161.3(5) . . . . ? C13 C12 C16 O7 -158.0(5) . . . . ? C11 C12 C16 O7 21.3(7) . . . . ? N3 C19 C20 C21 169.9(6) . . . . ? C19 C20 C21 C22 66.2(10) . . . . ? C20 C21 C22 C23 -178.1(7) . . . . ? C21 C22 C23 C23 179.0(8) . . . 2_768 ? N6 C26 C27 C28 -177.7(10) . . . . ? C26 C27 C28 C29 173.3(12) . . . . ? C27 C28 C29 C30 -67(2) . . . . ? C28 C29 C30 C32 -160(2) . . . . ? C33 C31 C32 C30 -166(3) . . . . ? C29 C30 C32 C31 -176(2) . . . . ? C32 C31 C33 C34 7(5) . . . . ? C31 C33 C34 C35 -95(2) . . . . ? C33 C34 C35 N7 -168.8(12) . . . . ? N3 C18 N1 C17 0.4(6) . . . . ? N3 C18 N1 Cd1 174.2(3) . . . . ? O6 Cd1 N1 C18 31.5(5) . . . . ? O2 Cd1 N1 C18 117.4(4) . . . . ? O8 Cd1 N1 C18 -136.2(4) 1_455 . . . ? O5 Cd1 N1 C18 -69.3(4) 2_667 . . . ? O7 Cd1 N1 C18 -165.2(4) 1_455 . . . ? O6 Cd1 N1 C17 -156.4(4) . . . . ? O2 Cd1 N1 C17 -70.5(5) . . . . ? O8 Cd1 N1 C17 35.9(6) 1_455 . . . ? O5 Cd1 N1 C17 102.7(5) 2_667 . . . ? O7 Cd1 N1 C17 6.8(5) 1_455 . . . ? N3 N2 C17 N1 -1.0(7) . . . . ? C18 N1 C17 N2 0.4(7) . . . . ? Cd1 N1 C17 N2 -173.2(4) . . . . ? N1 C18 N3 N2 -1.0(7) . . . . ? N1 C18 N3 C19 177.9(5) . . . . ? C17 N2 N3 C18 1.1(7) . . . . ? C17 N2 N3 C19 -177.8(5) . . . . ? C20 C19 N3 C18 116.0(7) . . . . ? C20 C19 N3 N2 -65.3(8) . . . . ? N6 C24 N4 C25 -1.0(6) . . . . ? N6 C24 N4 Cd2 -170.7(4) . . . . ? N5 C25 N4 C24 0.4(8) . . . . ? N5 C25 N4 Cd2 169.7(5) . . . . ? O1 Cd2 N4 C24 -27.8(5) . . . . ? N9 Cd2 N4 C24 143.6(10) 1_454 . . . ? O3 Cd2 N4 C24 114.1(5) 1_455 . . . ? O7 Cd2 N4 C24 -138.3(5) 1_455 . . . ? O4 Cd2 N4 C24 58.7(5) 1_455 . . . ? C8 Cd2 N4 C24 86.4(5) 1_455 . . . ? O1 Cd2 N4 C25 165.2(5) . . . . ? N9 Cd2 N4 C25 -23.3(14) 1_454 . . . ? O3 Cd2 N4 C25 -52.9(5) 1_455 . . . ? O7 Cd2 N4 C25 54.8(5) 1_455 . . . ? O4 Cd2 N4 C25 -108.3(5) 1_455 . . . ? C8 Cd2 N4 C25 -80.6(5) 1_455 . . . ? N4 C25 N5 N6 0.3(8) . . . . ? N4 C24 N6 N5 1.3(7) . . . . ? N4 C24 N6 C26 -176.7(6) . . . . ? C25 N5 N6 C24 -0.9(7) . . . . ? C25 N5 N6 C26 177.2(6) . . . . ? C27 C26 N6 C24 88.0(9) . . . . ? C27 C26 N6 N5 -89.7(8) . . . . ? N9 C36 N7 N8 -2.3(13) . . . . ? N9 C36 N7 C35 -156.8(13) . . . . ? C34 C35 N7 C36 -88(2) . . . . ? C34 C35 N7 N8 117.8(17) . . . . ? N9 C37 N8 N7 -1.5(12) . . . . ? C36 N7 N8 C37 2.3(14) . . . . ? C35 N7 N8 C37 163.2(10) . . . . ? N7 C36 N9 C37 1.3(10) . . . . ? N7 C36 N9 Cd2 178.6(6) . . . 1_656 ? N8 C37 N9 C36 0.3(10) . . . . ? N8 C37 N9 Cd2 -176.6(6) . . . 1_656 ? O2 C1 O1 Cd2 1.6(8) . . . . ? C2 C1 O1 Cd2 -176.6(4) . . . . ? N9 Cd2 O1 C1 62.8(4) 1_454 . . . ? N4 Cd2 O1 C1 -118.5(4) . . . . ? O3 Cd2 O1 C1 158.5(4) 1_455 . . . ? O7 Cd2 O1 C1 -31.8(5) 1_455 . . . ? O4 Cd2 O1 C1 157.6(4) 1_455 . . . ? C8 Cd2 O1 C1 160.0(4) 1_455 . . . ? O1 C1 O2 Cd1 89.6(8) . . . . ? C2 C1 O2 Cd1 -92.2(7) . . . . ? N1 Cd1 O2 C1 7.0(6) . . . . ? O6 Cd1 O2 C1 130.9(6) . . . . ? O8 Cd1 O2 C1 -139.3(5) 1_455 . . . ? O5 Cd1 O2 C1 -44.3(12) 2_667 . . . ? O7 Cd1 O2 C1 -90.0(6) 1_455 . . . ? O4 C8 O3 Cd2 -7.8(6) . . . 1_655 ? C6 C8 O3 Cd2 173.0(5) . . . 1_655 ? O3 C8 O4 Cd2 7.6(6) . . . 1_655 ? C6 C8 O4 Cd2 -173.3(5) . . . 1_655 ? O6 C9 O5 Cd1 -105.5(5) . . . 2_667 ? C10 C9 O5 Cd1 73.9(5) . . . 2_667 ? O5 C9 O6 Cd1 0.3(6) . . . . ? C10 C9 O6 Cd1 -179.1(3) . . . . ? N1 Cd1 O6 C9 -33.6(4) . . . . ? O2 Cd1 O6 C9 -121.0(3) . . . . ? O8 Cd1 O6 C9 139.3(3) 1_455 . . . ? O5 Cd1 O6 C9 58.2(3) 2_667 . . . ? O7 Cd1 O6 C9 170.9(3) 1_455 . . . ? O8 C16 O7 Cd2 -117.3(5) . . . 1_655 ? C12 C16 O7 Cd2 60.0(5) . . . 1_655 ? O8 C16 O7 Cd1 -4.3(5) . . . 1_655 ? C12 C16 O7 Cd1 173.1(4) . . . 1_655 ? O7 C16 O8 Cd1 4.7(6) . . . 1_655 ? C12 C16 O8 Cd1 -172.6(4) . . . 1_655 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.594 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 961132' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_comp1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 Cl2 N6 Zn' _chemical_formula_weight 412.66 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' Cl Cl 0.1484 0.1585 '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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.429(3) _cell_length_b 5.8100(10) _cell_length_c 25.244(5) _cell_angle_alpha 90.00 _cell_angle_beta 130.351(12) _cell_angle_gamma 90.00 _cell_volume 1948.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4202 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 28.7 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 1.542 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.649 _exptl_absorpt_correction_T_max 0.733 _exptl_absorpt_process_details ? _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7655 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.1744 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 28.74 _reflns_number_total 4202 _reflns_number_gt 1515 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4202 _refine_ls_number_parameters 208 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1255 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0373 _refine_ls_wR_factor_gt 0.0334 _refine_ls_goodness_of_fit_ref 0.635 _refine_ls_restrained_S_all 0.641 _refine_ls_shift/su_max 0.003 _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 Zn1 Zn -0.24308(3) 0.40583(5) 0.360539(18) 0.05389(11) Uani 1 1 d . . . C1 C -0.1006(2) 0.7514(5) 0.37518(16) 0.0586(9) Uani 1 1 d . . . H1 H -0.0631 0.7659 0.4229 0.070 Uiso 1 1 calc R . . N2 N -0.1511(2) 0.8033(6) 0.27197(16) 0.1136(12) Uani 1 1 d . . . C3 C -0.0149(2) 1.0599(5) 0.36176(17) 0.0816(10) Uani 1 1 d . . . H3A H 0.0281 1.0777 0.4118 0.098 Uiso 1 1 calc R . . H3B H -0.0523 1.2019 0.3404 0.098 Uiso 1 1 calc R . . C4 C 0.0505(2) 1.0189(5) 0.34235(15) 0.0740(9) Uani 1 1 d . . . H4A H 0.0074 1.0080 0.2922 0.089 Uiso 1 1 calc R . . H4B H 0.0944 1.1506 0.3571 0.089 Uiso 1 1 calc R . . C5 C 0.1139(2) 0.8054(5) 0.37399(14) 0.0608(8) Uani 1 1 d . . . H5A H 0.0706 0.6713 0.3521 0.073 Uiso 1 1 calc R . . H5B H 0.1472 0.8009 0.4230 0.073 Uiso 1 1 calc R . . C6 C 0.1933(2) 0.7938(4) 0.36576(14) 0.0634(9) Uani 1 1 d . . . H6A H 0.1598 0.8082 0.3168 0.076 Uiso 1 1 calc R . . H6B H 0.2382 0.9243 0.3897 0.076 Uiso 1 1 calc R . . C7 C 0.2552(2) 0.5763(5) 0.39325(13) 0.0618(8) Uani 1 1 d . . . H7A H 0.2108 0.4462 0.3677 0.074 Uiso 1 1 calc R . . H7B H 0.2861 0.5576 0.4416 0.074 Uiso 1 1 calc R . . C8 C 0.33676(19) 0.5730(5) 0.38796(13) 0.0592(8) Uani 1 1 d . . . H8A H 0.3839 0.6963 0.4164 0.071 Uiso 1 1 calc R . . H8B H 0.3064 0.6041 0.3402 0.071 Uiso 1 1 calc R . . C9 C 0.3946(2) 0.3481(4) 0.41035(13) 0.0576(8) Uani 1 1 d . . . H9A H 0.3472 0.2224 0.3851 0.069 Uiso 1 1 calc R . . H9B H 0.4309 0.3242 0.4595 0.069 Uiso 1 1 calc R . . C10 C 0.4690(2) 0.3429(4) 0.39771(14) 0.0622(8) Uani 1 1 d . . . H10A H 0.4336 0.3838 0.3496 0.075 Uiso 1 1 calc R . . H10B H 0.5201 0.4593 0.4266 0.075 Uiso 1 1 calc R . . C11 C 0.52100(19) 0.1123(5) 0.41257(13) 0.0574(8) Uani 1 1 d . . . H11A H 0.5604 0.0730 0.4612 0.069 Uiso 1 1 calc R . . H11B H 0.4710 -0.0072 0.3849 0.069 Uiso 1 1 calc R . . C12 C 0.5888(2) 0.1278(5) 0.39506(15) 0.0716(9) Uani 1 1 d . . . H12A H 0.5482 0.1675 0.3463 0.086 Uiso 1 1 calc R . . H12B H 0.6366 0.2516 0.4220 0.086 Uiso 1 1 calc R . . C13 C 0.6456(2) -0.2037(5) 0.36411(15) 0.0557(9) Uani 1 1 d . . . H13 H 0.6043 -0.1760 0.3166 0.067 Uiso 1 1 calc R . . C14 C 0.7535(2) -0.3384(5) 0.46408(17) 0.0658(9) Uani 1 1 d . . . H14 H 0.8045 -0.4313 0.5003 0.079 Uiso 1 1 calc R . . Cl1 Cl -0.13124(6) 0.18540(13) 0.45127(4) 0.0787(3) Uani 1 1 d . . . Cl2 Cl -0.37562(6) 0.25214(13) 0.26152(4) 0.0843(3) Uani 1 1 d . . . N1 N -0.17566(19) 0.6054(4) 0.33575(14) 0.0552(7) Uani 1 1 d . . . C2 C -0.2031(3) 0.6443(7) 0.27279(18) 0.1018(13) Uani 1 1 d U . . H2 H -0.2551 0.5641 0.2331 0.122 Uiso 1 1 calc R . . N3 N -0.0852(2) 0.8726(5) 0.33968(16) 0.0629(7) Uani 1 1 d . . . N4 N 0.64437(18) -0.0831(4) 0.40826(14) 0.0560(7) Uani 1 1 d . . . N5 N 0.7140(2) -0.1672(5) 0.47342(14) 0.0703(8) Uani 1 1 d . . . N6 N 0.71369(18) -0.3684(4) 0.39743(13) 0.0489(6) Uani 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 Zn1 0.0551(2) 0.0548(2) 0.0603(2) -0.0019(2) 0.0411(2) 0.0013(2) C1 0.075(3) 0.059(2) 0.068(2) -0.0019(19) 0.058(3) -0.0020(19) N2 0.068(3) 0.177(4) 0.067(2) 0.027(2) 0.031(2) -0.033(2) C3 0.083(3) 0.054(2) 0.138(3) 0.010(2) 0.085(3) 0.003(2) C4 0.067(3) 0.065(2) 0.109(3) 0.014(2) 0.066(2) 0.0012(19) C5 0.055(2) 0.062(2) 0.076(2) 0.0106(17) 0.047(2) 0.0088(18) C6 0.057(2) 0.063(2) 0.080(2) 0.0042(17) 0.048(2) 0.0019(17) C7 0.062(2) 0.064(2) 0.078(2) -0.0025(18) 0.054(2) 0.0025(19) C8 0.055(2) 0.061(2) 0.070(2) -0.0032(18) 0.0442(19) 0.0022(19) C9 0.062(2) 0.062(2) 0.063(2) -0.0032(16) 0.0470(19) -0.0003(17) C10 0.065(2) 0.059(2) 0.075(2) 0.0013(16) 0.051(2) 0.0027(17) C11 0.061(2) 0.056(2) 0.0682(19) 0.0003(17) 0.0481(19) 0.0006(18) C12 0.096(3) 0.049(2) 0.107(2) 0.0090(18) 0.083(2) 0.0105(19) C13 0.057(2) 0.063(2) 0.066(2) -0.0016(19) 0.048(2) -0.0011(18) C14 0.063(2) 0.072(3) 0.065(3) 0.0080(19) 0.043(2) 0.0158(18) Cl1 0.0788(7) 0.0748(6) 0.0756(6) 0.0150(4) 0.0470(6) 0.0231(5) Cl2 0.0833(7) 0.0951(7) 0.0624(6) -0.0153(5) 0.0417(6) -0.0228(5) N1 0.0494(19) 0.0688(18) 0.0542(17) 0.0022(16) 0.0366(16) -0.0005(15) C2 0.067(3) 0.159(4) 0.063(3) 0.002(3) 0.035(2) -0.031(3) N3 0.058(2) 0.073(2) 0.077(2) 0.0105(18) 0.0521(19) 0.0018(16) N4 0.065(2) 0.0476(16) 0.0722(19) 0.0047(16) 0.0522(19) 0.0112(15) N5 0.079(2) 0.072(2) 0.064(2) -0.0037(16) 0.0482(19) 0.0061(16) N6 0.0448(17) 0.0514(17) 0.0511(16) 0.0037(14) 0.0314(15) 0.0066(14) _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 Zn1 N6 2.016(2) 1_465 ? Zn1 N1 2.017(2) . ? Zn1 Cl1 2.2145(9) . ? Zn1 Cl2 2.2146(10) . ? C1 N3 1.297(3) . ? C1 N1 1.318(3) . ? C1 H1 0.9300 . ? N2 C2 1.304(4) . ? N2 N3 1.364(3) . ? C3 N3 1.453(3) . ? C3 C4 1.523(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.502(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.527(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.508(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.512(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.518(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.523(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.522(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.508(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N4 1.461(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N6 1.319(3) . ? C13 N4 1.328(3) . ? C13 H13 0.9300 . ? C14 N5 1.315(3) . ? C14 N6 1.353(3) . ? C14 H14 0.9300 . ? N1 C2 1.349(3) . ? C2 H2 0.9300 . ? N4 N5 1.354(3) . ? N6 Zn1 2.016(2) 1_645 ? 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 Zn1 N1 103.66(8) 1_465 . ? N6 Zn1 Cl1 103.92(8) 1_465 . ? N1 Zn1 Cl1 110.72(8) . . ? N6 Zn1 Cl2 110.80(7) 1_465 . ? N1 Zn1 Cl2 105.85(8) . . ? Cl1 Zn1 Cl2 120.70(4) . . ? N3 C1 N1 112.1(3) . . ? N3 C1 H1 124.0 . . ? N1 C1 H1 124.0 . . ? C2 N2 N3 102.7(3) . . ? N3 C3 C4 112.4(2) . . ? N3 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? N3 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 113.9(2) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C6 112.5(2) . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C5 114.6(2) . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6B 108.6 . . ? C5 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C6 C7 C8 113.8(2) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C9 114.5(2) . . ? C7 C8 H8A 108.6 . . ? C9 C8 H8A 108.6 . . ? C7 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C8 C9 C10 112.9(2) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 114.7(2) . . ? C11 C10 H10A 108.6 . . ? C9 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C10 109.2(2) . . ? C12 C11 H11A 109.8 . . ? C10 C11 H11A 109.8 . . ? C12 C11 H11B 109.8 . . ? C10 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? N4 C12 C11 114.4(2) . . ? N4 C12 H12A 108.7 . . ? C11 C12 H12A 108.7 . . ? N4 C12 H12B 108.7 . . ? C11 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? N6 C13 N4 110.1(3) . . ? N6 C13 H13 124.9 . . ? N4 C13 H13 124.9 . . ? N5 C14 N6 114.4(3) . . ? N5 C14 H14 122.8 . . ? N6 C14 H14 122.8 . . ? C1 N1 C2 101.7(3) . . ? C1 N1 Zn1 128.9(2) . . ? C2 N1 Zn1 128.9(3) . . ? N2 C2 N1 114.7(3) . . ? N2 C2 H2 122.7 . . ? N1 C2 H2 122.7 . . ? C1 N3 N2 108.8(3) . . ? C1 N3 C3 129.9(3) . . ? N2 N3 C3 121.2(3) . . ? C13 N4 N5 109.9(2) . . ? C13 N4 C12 128.3(3) . . ? N5 N4 C12 121.4(3) . . ? C14 N5 N4 102.5(2) . . ? C13 N6 C14 103.0(2) . . ? C13 N6 Zn1 129.0(2) . 1_645 ? C14 N6 Zn1 127.9(2) . 1_645 ? 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 N3 C3 C4 C5 -60.2(4) . . . . ? C3 C4 C5 C6 -168.6(3) . . . . ? C4 C5 C6 C7 -176.8(2) . . . . ? C5 C6 C7 C8 -177.1(2) . . . . ? C6 C7 C8 C9 -175.6(2) . . . . ? C7 C8 C9 C10 174.4(2) . . . . ? C8 C9 C10 C11 -174.1(2) . . . . ? C9 C10 C11 C12 177.6(2) . . . . ? C10 C11 C12 N4 179.1(2) . . . . ? N3 C1 N1 C2 1.6(4) . . . . ? N3 C1 N1 Zn1 -171.49(18) . . . . ? N6 Zn1 N1 C1 55.2(3) 1_465 . . . ? Cl1 Zn1 N1 C1 -55.7(3) . . . . ? Cl2 Zn1 N1 C1 171.9(3) . . . . ? N6 Zn1 N1 C2 -116.1(3) 1_465 . . . ? Cl1 Zn1 N1 C2 133.0(3) . . . . ? Cl2 Zn1 N1 C2 0.6(3) . . . . ? N3 N2 C2 N1 -0.2(4) . . . . ? C1 N1 C2 N2 -0.8(4) . . . . ? Zn1 N1 C2 N2 172.3(2) . . . . ? N1 C1 N3 N2 -1.8(4) . . . . ? N1 C1 N3 C3 176.0(3) . . . . ? C2 N2 N3 C1 1.2(4) . . . . ? C2 N2 N3 C3 -176.9(3) . . . . ? C4 C3 N3 C1 126.9(3) . . . . ? C4 C3 N3 N2 -55.5(4) . . . . ? N6 C13 N4 N5 0.4(3) . . . . ? N6 C13 N4 C12 172.8(3) . . . . ? C11 C12 N4 C13 124.0(3) . . . . ? C11 C12 N4 N5 -64.4(4) . . . . ? N6 C14 N5 N4 0.1(3) . . . . ? C13 N4 N5 C14 -0.3(3) . . . . ? C12 N4 N5 C14 -173.3(2) . . . . ? N4 C13 N6 C14 -0.3(3) . . . . ? N4 C13 N6 Zn1 -175.86(16) . . . 1_645 ? N5 C14 N6 C13 0.1(3) . . . . ? N5 C14 N6 Zn1 175.73(19) . . . 1_645 ? _diffrn_measured_fraction_theta_max 0.833 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.330 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 961133'