# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _publ_contact_author_email ENRIQUE.GARCIA-ES@UV.ES _publ_contact_author_name 'Prof Enrique Garcia-Espana' _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FM loop_ _publ_author_name E.Garcia-Espana M.Chadim P.Diaz J.Hodacova P.C.Junk J.Latorre ; J.M.Llinares ; C.Soriano J.Zavada data_compound1 _database_code_CSD 209937 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common janaB _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28.50 H35 N10 O14.50' _chemical_formula_weight 749.66 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' 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1875(12) _cell_length_b 13.3925(19) _cell_length_c 15.778(2) _cell_angle_alpha 92.796(3) _cell_angle_beta 92.386(3) _cell_angle_gamma 101.263(3) _cell_volume 1692.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9648 _exptl_absorpt_correction_T_max 0.9822 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 7904 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 23.31 _reflns_number_total 4854 _reflns_number_gt 3206 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1562P)^2^+0.2677P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.001(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4854 _refine_ls_number_parameters 513 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0989 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.2435 _refine_ls_wR_factor_gt 0.2123 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.069 _refine_ls_shift/su_mean 0.011 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 N1 N 0.3178(4) 0.4358(2) 0.83723(19) 0.0444(7) Uani 1 1 d . . . N2 N 0.1196(4) 0.2332(2) 0.81877(19) 0.0494(8) Uani 1 1 d . . . N3 N 0.1149(4) 0.2844(3) 0.6562(2) 0.0501(8) Uani 1 1 d . . . N4 N 0.4665(4) 0.3402(2) 0.70524(19) 0.0490(8) Uani 1 1 d . . . C1 C 0.5154(4) 0.5706(3) 0.7741(2) 0.0495(9) Uani 1 1 d . . . C2 C 0.4861(5) 0.6678(3) 0.7633(3) 0.0609(11) Uani 1 1 d . . . H2 H 0.4385 0.7016 0.8075 0.084(3) Uiso 1 1 calc R . . C3 C 0.5252(6) 0.7166(3) 0.6891(3) 0.0710(12) Uani 1 1 d . . . H3 H 0.5020 0.7825 0.6817 0.084(3) Uiso 1 1 calc R . . C4 C 0.5978(5) 0.6685(4) 0.6263(3) 0.0683(12) Uani 1 1 d . . . H4 H 0.6255 0.7015 0.5754 0.084(3) Uiso 1 1 calc R . . C5 C 0.6306(5) 0.5726(3) 0.6367(2) 0.0583(10) Uani 1 1 d . . . H5 H 0.6812 0.5403 0.5928 0.084(3) Uiso 1 1 calc R . . C6 C 0.5908(4) 0.5222(3) 0.7104(2) 0.0490(9) Uani 1 1 d . . . C7 C 0.4668(5) 0.5198(3) 0.8548(2) 0.0572(10) Uani 1 1 d . . . H7A H 0.5609 0.4917 0.8785 0.084(3) Uiso 1 1 calc R . . H7B H 0.4408 0.5706 0.8972 0.084(3) Uiso 1 1 calc R . . C8 C 0.2592(5) 0.3806(3) 0.9129(2) 0.0518(9) Uani 1 1 d . . . H8A H 0.2406 0.4299 0.9585 0.084(3) Uiso 1 1 calc R . . H8B H 0.3456 0.3443 0.9343 0.084(3) Uiso 1 1 calc R . . C9 C 0.0992(4) 0.3048(3) 0.8907(2) 0.0519(9) Uani 1 1 d . . . H9A H 0.0654 0.2658 0.9409 0.084(3) Uiso 1 1 calc R . . H9B H 0.0098 0.3418 0.8751 0.084(3) Uiso 1 1 calc R . . C10 C -0.0351(5) 0.1600(3) 0.7931(3) 0.0662(11) Uani 1 1 d . . . H10A H -0.0068 0.0948 0.7723 0.084(3) Uiso 1 1 calc R . . H10B H -0.1031 0.1464 0.8433 0.084(3) Uiso 1 1 calc R . . C11 C -0.1329(6) 0.1972(4) 0.7268(3) 0.0873(15) Uani 1 1 d . . . H11A H -0.1618 0.2616 0.7491 0.084(3) Uiso 1 1 calc R . . H11B H -0.2386 0.1470 0.7157 0.084(3) Uiso 1 1 calc R . . C12 C -0.0538(5) 0.2166(3) 0.6437(3) 0.0641(11) Uani 1 1 d . . . H12A H -0.0431 0.1508 0.6151 0.084(3) Uiso 1 1 calc R . . H12B H -0.1262 0.2489 0.6065 0.084(3) Uiso 1 1 calc R . . C13 C 0.2425(5) 0.2524(3) 0.6038(3) 0.0579(10) Uani 1 1 d . . . H13A H 0.2037 0.2473 0.5432 0.084(3) Uiso 1 1 calc R . . H13B H 0.2582 0.1840 0.6195 0.084(3) Uiso 1 1 calc R . . C14 C 0.4061(5) 0.3264(3) 0.6159(2) 0.0574(10) Uani 1 1 d . . . H14A H 0.4899 0.3012 0.5816 0.084(3) Uiso 1 1 calc R . . H14B H 0.3927 0.3931 0.5951 0.084(3) Uiso 1 1 calc R . . C15 C 0.6228(5) 0.4160(3) 0.7183(3) 0.0584(10) Uani 1 1 d . . . H15A H 0.7020 0.4021 0.6756 0.084(3) Uiso 1 1 calc R . . H15B H 0.6739 0.4104 0.7754 0.084(3) Uiso 1 1 calc R . . O1A O 0.0817(3) 0.4827(2) 0.71872(16) 0.0594(7) Uani 1 1 d . . . N1A N -0.0401(4) 0.5936(3) 0.8526(2) 0.0574(9) Uani 1 1 d . . . O2A O 0.0293(5) 0.5293(3) 0.8793(2) 0.0978(12) Uani 1 1 d . . . O3A O -0.1416(5) 0.6264(3) 0.8931(2) 0.1036(13) Uani 1 1 d . . . N2A N -0.0352(6) 0.8696(3) 0.6670(4) 0.0914(13) Uani 1 1 d . . . O4A O -0.0960(7) 0.9128(3) 0.7229(3) 0.1261(16) Uani 1 1 d . . . O5A O -0.0040(6) 0.9055(3) 0.5984(3) 0.1226(15) Uani 1 1 d . . . N3A N 0.1614(4) 0.5720(3) 0.5590(2) 0.0643(10) Uani 1 1 d . . . O6A O 0.2207(5) 0.6261(3) 0.5019(2) 0.1075(13) Uani 1 1 d . . . O7A O 0.1569(5) 0.4813(3) 0.5564(2) 0.0877(11) Uani 1 1 d . . . C1A C 0.0610(4) 0.5711(3) 0.7069(2) 0.0450(9) Uani 1 1 d . . . C2A C -0.0006(4) 0.6338(3) 0.7704(2) 0.0469(9) Uani 1 1 d . . . C3A C -0.0310(5) 0.7284(3) 0.7582(3) 0.0588(10) Uani 1 1 d . . . H3A H -0.0754 0.7648 0.8019 0.084(3) Uiso 1 1 calc R . . C4A C 0.0037(5) 0.7707(3) 0.6813(3) 0.0619(11) Uani 1 1 d . . . C5A C 0.0692(5) 0.7199(3) 0.6178(3) 0.0585(10) Uani 1 1 d . . . H5A H 0.0966 0.7513 0.5662 0.084(3) Uiso 1 1 calc R . . C6A C 0.0949(4) 0.6225(3) 0.6295(2) 0.0512(9) Uani 1 1 d . . . O1B O 0.4701(4) 0.2076(2) 0.84759(19) 0.0708(8) Uani 1 1 d . . . N1B N 0.6862(5) 0.2603(3) 0.9978(3) 0.0727(10) Uani 1 1 d . . . O2B O 0.6808(6) 0.3351(3) 0.9575(3) 0.1136(14) Uani 1 1 d . . . O3B O 0.7258(6) 0.2655(3) 1.0738(3) 0.1143(14) Uani 1 1 d . . . N2B N 0.7730(6) -0.0869(4) 0.9862(3) 0.0836(12) Uani 1 1 d . . . O4B O 0.8573(5) -0.0639(3) 1.0524(3) 0.1020(13) Uani 1 1 d . . . O5B O 0.7458(7) -0.1719(4) 0.9509(3) 0.1400(19) Uani 1 1 d . . . N3B N 0.4154(6) 0.0093(4) 0.7661(3) 0.0861(12) Uani 1 1 d . . . O6B O 0.3962(11) 0.0711(5) 0.7179(4) 0.208(4) Uani 1 1 d . . . O7B O 0.3532(8) -0.0758(4) 0.7514(4) 0.173(3) Uani 1 1 d . . . C1B C 0.5421(4) 0.1424(3) 0.8773(2) 0.0510(9) Uani 1 1 d . . . C2B C 0.6508(4) 0.1596(3) 0.9525(2) 0.0492(9) Uani 1 1 d . . . C3B C 0.7234(4) 0.0862(3) 0.9880(2) 0.0562(10) Uani 1 1 d . . . H3B H 0.7911 0.1017 1.0391 0.084(3) Uiso 1 1 calc R . . C4B C 0.6970(5) -0.0101(3) 0.9485(3) 0.0581(11) Uani 1 1 d . . . C5B C 0.5956(5) -0.0348(3) 0.8757(3) 0.0599(10) Uani 1 1 d . . . H5B H 0.5768 -0.1017 0.8492 0.084(3) Uiso 1 1 calc R . . C6B C 0.5226(5) 0.0391(3) 0.8423(3) 0.0564(10) Uani 1 1 d . . . C1S C 0.4797(18) -0.0424(9) 0.4860(8) 0.102(4) Uani 0.50 1 d P . . C2S C 0.3594(12) 0.0173(8) 0.4762(7) 0.181(4) Uani 1 1 d . . . O1S O 0.4313(18) -0.1280(10) 0.4609(13) 0.232(8) Uani 0.50 1 d P . . H1NA H 0.243(4) 0.459(2) 0.818(2) 0.031(9) Uiso 1 1 d . . . H1NB H 0.355(5) 0.394(3) 0.796(3) 0.058(11) Uiso 1 1 d . . . H2NA H 0.205(8) 0.202(5) 0.841(4) 0.13(2) Uiso 1 1 d . . . H3NA H 0.115(6) 0.346(4) 0.648(3) 0.091(17) Uiso 1 1 d . . . H3NB H 0.135(5) 0.274(3) 0.715(3) 0.079(14) Uiso 1 1 d . . . H4NA H 0.489(4) 0.283(3) 0.717(2) 0.046(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0449(17) 0.0559(19) 0.0342(17) 0.0061(14) 0.0025(14) 0.0135(15) N2 0.0521(18) 0.0544(18) 0.0432(18) 0.0094(14) 0.0046(14) 0.0119(15) N3 0.0564(19) 0.050(2) 0.044(2) 0.0064(16) 0.0072(15) 0.0082(15) N4 0.0576(19) 0.0495(19) 0.0441(18) 0.0108(15) 0.0069(14) 0.0182(16) C1 0.052(2) 0.050(2) 0.043(2) 0.0030(17) 0.0023(16) 0.0015(17) C2 0.069(3) 0.054(2) 0.055(2) -0.0031(19) 0.011(2) 0.0019(19) C3 0.081(3) 0.055(2) 0.074(3) 0.013(2) 0.000(2) 0.005(2) C4 0.071(3) 0.077(3) 0.050(2) 0.016(2) 0.007(2) -0.005(2) C5 0.055(2) 0.069(3) 0.046(2) 0.0021(19) 0.0103(18) 0.0015(19) C6 0.0434(19) 0.055(2) 0.045(2) 0.0006(17) 0.0021(16) 0.0015(16) C7 0.066(2) 0.060(2) 0.041(2) -0.0025(18) 0.0042(18) 0.0024(19) C8 0.061(2) 0.064(2) 0.0339(19) 0.0102(17) 0.0080(17) 0.0187(19) C9 0.057(2) 0.058(2) 0.046(2) 0.0150(18) 0.0148(17) 0.0189(18) C10 0.065(3) 0.070(3) 0.059(3) 0.012(2) 0.008(2) -0.002(2) C11 0.065(3) 0.103(4) 0.083(4) 0.017(3) -0.007(3) -0.009(3) C12 0.054(2) 0.072(3) 0.059(3) 0.004(2) 0.0025(19) -0.003(2) C13 0.063(2) 0.065(2) 0.046(2) -0.0017(19) 0.0100(18) 0.012(2) C14 0.063(2) 0.068(3) 0.041(2) 0.0037(19) 0.0138(18) 0.011(2) C15 0.052(2) 0.070(3) 0.056(2) 0.004(2) 0.0038(18) 0.021(2) O1A 0.0764(18) 0.0655(17) 0.0431(15) 0.0069(13) 0.0048(13) 0.0295(14) N1A 0.063(2) 0.071(2) 0.0411(18) -0.0037(17) 0.0052(15) 0.0203(17) O2A 0.166(4) 0.086(2) 0.060(2) 0.0242(18) 0.036(2) 0.060(2) O3A 0.114(3) 0.155(4) 0.062(2) 0.011(2) 0.025(2) 0.071(3) N2A 0.116(4) 0.062(3) 0.099(4) 0.013(3) -0.013(3) 0.026(2) O4A 0.176(4) 0.066(2) 0.145(4) -0.005(3) 0.003(3) 0.049(3) O5A 0.164(4) 0.087(3) 0.128(4) 0.046(3) -0.004(3) 0.046(3) N3A 0.061(2) 0.093(3) 0.044(2) 0.0143(19) 0.0086(16) 0.025(2) O6A 0.127(3) 0.140(3) 0.067(2) 0.035(2) 0.045(2) 0.037(3) O7A 0.127(3) 0.097(3) 0.0559(19) 0.0071(17) 0.0210(18) 0.060(2) C1A 0.0431(19) 0.050(2) 0.042(2) 0.0011(16) -0.0027(15) 0.0110(16) C2A 0.0479(19) 0.054(2) 0.038(2) 0.0018(16) -0.0008(15) 0.0098(17) C3A 0.059(2) 0.058(2) 0.058(3) -0.009(2) -0.0069(19) 0.0139(19) C4A 0.065(2) 0.050(2) 0.071(3) 0.009(2) -0.012(2) 0.0121(19) C5A 0.056(2) 0.066(3) 0.052(2) 0.014(2) -0.0017(18) 0.009(2) C6A 0.048(2) 0.068(2) 0.040(2) 0.0104(18) 0.0026(16) 0.0148(18) O1B 0.0762(19) 0.0749(19) 0.072(2) 0.0229(15) 0.0037(15) 0.0370(16) N1B 0.069(2) 0.078(3) 0.074(3) -0.001(2) 0.008(2) 0.0192(19) O2B 0.143(4) 0.064(2) 0.136(4) 0.004(2) -0.021(3) 0.032(2) O3B 0.150(4) 0.115(3) 0.066(3) -0.023(2) 0.000(2) 0.007(3) N2B 0.094(3) 0.085(3) 0.086(3) 0.042(3) 0.014(2) 0.042(2) O4B 0.099(3) 0.123(3) 0.096(3) 0.054(2) -0.005(2) 0.042(2) O5B 0.214(5) 0.089(3) 0.141(4) 0.026(3) -0.013(4) 0.088(3) N3B 0.104(3) 0.071(3) 0.081(3) -0.003(2) -0.032(2) 0.022(2) O6B 0.335(9) 0.132(4) 0.140(5) 0.001(4) -0.150(6) 0.041(5) O7B 0.199(5) 0.099(4) 0.204(6) -0.040(4) -0.116(5) 0.029(3) C1B 0.047(2) 0.060(2) 0.052(2) 0.0143(18) 0.0148(17) 0.0190(18) C2B 0.049(2) 0.055(2) 0.046(2) 0.0041(18) 0.0104(17) 0.0138(17) C3B 0.049(2) 0.079(3) 0.045(2) 0.020(2) 0.0088(17) 0.017(2) C4B 0.063(2) 0.059(3) 0.061(3) 0.026(2) 0.015(2) 0.025(2) C5B 0.066(2) 0.056(2) 0.061(3) 0.014(2) 0.011(2) 0.016(2) C6B 0.059(2) 0.060(2) 0.051(2) 0.0104(19) 0.0007(18) 0.0127(19) C1S 0.124(10) 0.068(7) 0.115(10) -0.016(7) 0.005(8) 0.029(7) C2S 0.142(7) 0.199(9) 0.204(10) -0.068(8) -0.050(7) 0.073(7) O1S 0.172(12) 0.114(9) 0.41(3) -0.048(12) -0.018(13) 0.037(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C8 1.483(5) . ? N1 C7 1.495(5) . ? N2 C10 1.470(5) . ? N2 C9 1.486(5) . ? N3 C13 1.473(5) . ? N3 C12 1.497(5) . ? N4 C14 1.466(5) . ? N4 C15 1.470(5) . ? C1 C2 1.386(5) . ? C1 C6 1.398(5) . ? C1 C7 1.504(5) . ? C2 C3 1.388(6) . ? C3 C4 1.373(6) . ? C4 C5 1.379(6) . ? C5 C6 1.392(5) . ? C6 C15 1.506(5) . ? C8 C9 1.509(5) . ? C10 C11 1.457(6) . ? C11 C12 1.498(6) . ? C13 C14 1.502(5) . ? O1A O1A 0.000(10) 1 ? O1A C1A 1.250(4) . ? N1A O3A 1.204(4) . ? N1A O2A 1.204(4) 1 ? N1A O2A 1.204(4) . ? N1A C2A 1.454(5) . ? O2A O2A 0.000(13) 1 ? N2A O4A 1.208(6) . ? N2A O5A 1.222(6) . ? N2A C4A 1.447(6) . ? N3A O7A 1.207(5) 1 ? N3A O7A 1.207(5) . ? N3A O6A 1.238(5) . ? N3A C6A 1.454(5) . ? O7A O7A 0.000(14) 1 ? C1A O1A 1.250(4) 1 ? C1A C6A 1.441(5) . ? C1A C2A 1.445(5) . ? C2A C3A 1.358(5) . ? C3A C4A 1.382(6) . ? C4A C5A 1.369(6) . ? C5A C6A 1.380(5) . ? O1B O1B 0.000(6) 1 ? O1B C1B 1.244(4) . ? N1B O2B 1.219(5) . ? N1B O3B 1.223(5) . ? N1B C2B 1.466(6) . ? N2B O4B 1.219(6) . ? N2B O5B 1.219(6) . ? N2B C4B 1.441(5) . ? N3B O7B 1.163(6) . ? N3B O6B 1.179(6) . ? N3B C6B 1.449(6) . ? C1B O1B 1.244(4) 1 ? C1B C2B 1.435(6) . ? C1B C6B 1.441(6) . ? C2B C3B 1.374(5) . ? C3B C4B 1.379(6) . ? C4B C5B 1.376(6) . ? C5B C6B 1.368(5) . ? C1S O1S 1.180(14) . ? C1S C1S 1.18(2) 2_656 ? C1S C2S 1.393(14) . ? C1S C2S 1.395(15) 2_656 ? C2S C1S 1.395(15) 2_656 ? 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 C8 N1 C7 114.4(3) . . ? C10 N2 C9 113.0(3) . . ? C13 N3 C12 114.1(3) . . ? C14 N4 C15 112.2(3) . . ? C2 C1 C6 119.5(3) . . ? C2 C1 C7 119.1(3) . . ? C6 C1 C7 121.4(3) . . ? C1 C2 C3 121.1(4) . . ? C4 C3 C2 119.2(4) . . ? C3 C4 C5 120.4(4) . . ? C4 C5 C6 121.1(4) . . ? C5 C6 C1 118.7(3) . . ? C5 C6 C15 119.6(3) . . ? C1 C6 C15 121.7(3) . . ? N1 C7 C1 110.0(3) . . ? N1 C8 C9 110.4(3) . . ? N2 C9 C8 111.1(3) . . ? C11 C10 N2 112.2(4) . . ? C10 C11 C12 117.0(4) . . ? N3 C12 C11 111.2(4) . . ? N3 C13 C14 111.5(3) . . ? N4 C14 C13 111.7(3) . . ? N4 C15 C6 110.6(3) . . ? O1A O1A C1A 0(10) 1 . ? O3A N1A O2A 121.3(4) . 1 ? O3A N1A O2A 121.3(4) . . ? O2A N1A O2A 0.0(3) 1 . ? O3A N1A C2A 118.8(3) . . ? O2A N1A C2A 119.9(3) 1 . ? O2A N1A C2A 119.9(3) . . ? O2A O2A N1A 0(10) 1 . ? O4A N2A O5A 123.2(5) . . ? O4A N2A C4A 118.9(5) . . ? O5A N2A C4A 117.8(5) . . ? O7A N3A O7A 0.0(3) 1 . ? O7A N3A O6A 122.1(4) 1 . ? O7A N3A O6A 122.1(4) . . ? O7A N3A C6A 121.0(3) 1 . ? O7A N3A C6A 121.0(3) . . ? O6A N3A C6A 117.0(4) . . ? O7A O7A N3A 0(10) 1 . ? O1A C1A O1A 0.0(2) 1 . ? O1A C1A C6A 124.6(3) 1 . ? O1A C1A C6A 124.6(3) . . ? O1A C1A C2A 123.3(3) 1 . ? O1A C1A C2A 123.3(3) . . ? C6A C1A C2A 112.1(3) . . ? C3A C2A C1A 124.6(3) . . ? C3A C2A N1A 116.2(3) . . ? C1A C2A N1A 119.2(3) . . ? C2A C3A C4A 119.0(4) . . ? C5A C4A C3A 121.4(4) . . ? C5A C4A N2A 119.6(4) . . ? C3A C4A N2A 119.0(4) . . ? C4A C5A C6A 119.4(4) . . ? C5A C6A C1A 123.5(3) . . ? C5A C6A N3A 116.6(3) . . ? C1A C6A N3A 119.9(3) . . ? O1B O1B C1B 0(10) 1 . ? O2B N1B O3B 123.2(5) . . ? O2B N1B C2B 118.5(4) . . ? O3B N1B C2B 118.3(4) . . ? O4B N2B O5B 123.8(4) . . ? O4B N2B C4B 118.4(5) . . ? O5B N2B C4B 117.8(5) . . ? O7B N3B O6B 120.2(5) . . ? O7B N3B C6B 119.9(5) . . ? O6B N3B C6B 119.8(5) . . ? O1B C1B O1B 0.0(4) 1 . ? O1B C1B C2B 124.2(4) 1 . ? O1B C1B C2B 124.2(4) . . ? O1B C1B C6B 124.4(4) 1 . ? O1B C1B C6B 124.4(4) . . ? C2B C1B C6B 111.4(3) . . ? C3B C2B C1B 124.3(4) . . ? C3B C2B N1B 115.9(4) . . ? C1B C2B N1B 119.7(3) . . ? C2B C3B C4B 119.2(4) . . ? C5B C4B C3B 121.3(4) . . ? C5B C4B N2B 119.7(4) . . ? C3B C4B N2B 118.9(4) . . ? C6B C5B C4B 118.4(4) . . ? C5B C6B C1B 125.4(4) . . ? C5B C6B N3B 116.5(4) . . ? C1B C6B N3B 118.2(4) . . ? O1S C1S C1S 176(2) . 2_656 ? O1S C1S C2S 112.8(14) . . ? C1S C1S C2S 65.1(11) 2_656 . ? O1S C1S C2S 117.1(13) . 2_656 ? C1S C1S C2S 64.9(13) 2_656 2_656 ? C2S C1S C2S 130.0(10) . 2_656 ? C1S C2S C1S 50.0(10) . 2_656 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1NA O1A 0.79(3) 2.08(4) 2.813(4) 154(3) 1 N1 H1NA O2A 0.79(3) 2.37(3) 2.966(5) 133(3) 1 N2 H2NA O1B 0.95(6) 2.15(6) 2.975(4) 144(5) 1 N2 H2NA O4B 0.95(6) 2.55(6) 3.145(5) 121(5) 2_657 N3 H3NA O1A 0.84(5) 2.16(5) 2.856(4) 140(5) 1 N3 H3NA O7A 0.84(5) 2.36(6) 3.107(5) 149(5) 1 N4 H4NA O1B 0.85(4) 2.34(4) 2.933(4) 128(3) 1 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 23.31 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.682 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.059 data_ob232cu _database_code_CSD 209938 _audit_creation_date 2003-05-27T11:16:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C15 H26 Cl2 Cu N4 O4' _chemical_formula_weight 460.84 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y, -z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y, z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.4520(2) _cell_length_b 11.0000(3) _cell_length_c 19.3590(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2012.79(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 956 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.378 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_unetI/netI 0.0596 _diffrn_reflns_number 4286 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.1 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _reflns_number_total 2413 _reflns_number_gt 1343 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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_number_reflns 2413 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1042 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1754 _refine_ls_wR_factor_gt 0.128 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.634 _refine_diff_density_min -0.738 _refine_diff_density_rms 0.213 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cu1 Cu 0.25 0.03241(6) 0.25027(3) 0.0392(3) Uani 1 2 d S . . Cl1 Cl 0.25 0.27818(12) 0.26459(9) 0.0498(4) Uani 1 2 d S . . Cl2 Cl 0.75 0.27459(16) 0.12201(10) 0.0654(5) Uani 1 2 d S . . N1 N 0.0851(3) 0.0522(3) 0.18221(17) 0.0414(8) Uani 1 1 d . . . H1A H 0.0715 0.138 0.1762 0.05 Uiso 1 1 d R . . N2 N 0.0960(3) 0.0049(3) 0.32204(17) 0.0478(9) Uani 1 1 d . . . H2A H 0.0909 -0.0818 0.327 0.057 Uiso 1 1 d R . . C8 C -0.0425(4) 0.0049(5) 0.2185(3) 0.0576(12) Uani 1 1 d . . . H8A H -0.0431 -0.0832 0.2174 0.053(12) Uiso 1 1 calc R . . H8B H -0.1276 0.0342 0.1959 0.075(15) Uiso 1 1 calc R . . C7 C 0.0922(4) 0.0029(4) 0.1108(2) 0.0543(11) Uani 1 1 d . . . H7A H -0.0031 -0.0059 0.0929 0.068(13) Uiso 1 1 calc R . . H7B H 0.1352 -0.0771 0.112 0.094(17) Uiso 1 1 calc R . . C9 C -0.0374(4) 0.0493(4) 0.2921(3) 0.0606(13) Uani 1 1 d . . . H9A H -0.0405 0.1375 0.2935 0.049(11) Uiso 1 1 calc R . . H9B H -0.1174 0.018 0.318 0.071(14) Uiso 1 1 calc R . . O1 O 0.75 0.1657(6) 0.0836(3) 0.107(2) Uani 1 2 d S . . C1 C 0.1755(4) 0.0827(4) 0.0630(2) 0.0472(10) Uani 1 1 d . . . C2 C 0.1062(5) 0.1589(5) 0.0169(2) 0.0645(13) Uani 1 1 d . . . H2 H 0.0047 0.1587 0.0154 0.077 Uiso 1 1 d R . . C3 C 0.1771(5) 0.2312(5) -0.0290(3) 0.0733(15) Uani 1 1 d . . . H3 H 0.1283 0.2834 -0.0608 0.088 Uiso 1 1 d R . . O2 O 0.75 0.3846(6) 0.0847(3) 0.119(2) Uani 1 2 d S . . O3 O 0.6265(5) 0.2756(4) 0.1626(3) 0.150(2) Uani 1 1 d . . . C10 C 0.1162(5) 0.0464(5) 0.3938(3) 0.0688(14) Uani 1 1 d . . . H10A H 0.0358 0.0211 0.4214 0.094(17) Uiso 1 1 calc R . . H10B H 0.12 0.1345 0.3945 0.044(10) Uiso 1 1 calc R . . C11 C 0.25 -0.0039(9) 0.4250(4) 0.078(2) Uani 1 2 d S . . H11A H 0.25 -0.0916 0.4196 0.24(3) Uiso 2 2 calc SPR . . H11B H 0.25 0.0135 0.4742 0.42(6) Uiso 2 2 calc SPR . . 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 Cu1 0.0330(4) 0.0390(4) 0.0455(5) -0.0035(3) 0 0 Cl1 0.0535(9) 0.0260(7) 0.0699(11) -0.0001(7) 0 0 Cl2 0.0653(10) 0.0534(10) 0.0774(13) -0.0042(10) 0 0 N1 0.0329(16) 0.0368(18) 0.054(2) 0.0006(16) 0.0001(14) -0.0042(13) N2 0.055(2) 0.0329(18) 0.055(2) 0.0015(17) 0.0102(17) 0.0019(15) C8 0.032(2) 0.057(3) 0.083(4) 0.018(3) 0.001(2) -0.0058(19) C7 0.053(3) 0.051(3) 0.060(3) -0.008(2) -0.013(2) -0.009(2) C9 0.048(3) 0.053(3) 0.081(4) 0.013(3) 0.025(2) 0.004(2) O1 0.078(4) 0.104(5) 0.137(5) -0.061(5) 0 0 C1 0.055(2) 0.049(2) 0.038(2) -0.011(2) -0.0050(19) -0.001(2) C2 0.072(3) 0.068(3) 0.054(3) -0.008(3) -0.016(2) 0.000(3) C3 0.098(4) 0.071(3) 0.050(3) 0.003(3) -0.015(3) 0.006(3) O2 0.164(6) 0.111(5) 0.083(4) 0.042(4) 0 0 O3 0.159(4) 0.073(3) 0.217(6) -0.026(3) 0.119(4) -0.019(3) C10 0.094(4) 0.054(3) 0.058(3) -0.009(3) 0.022(3) -0.006(3) C11 0.111(6) 0.071(5) 0.051(5) -0.004(4) 0 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 2.035(3) 7_655 ? Cu1 N2 2.035(3) . ? Cu1 N1 2.053(3) . ? Cu1 N1 2.053(3) 7_655 ? Cu1 Cl1 2.7176(13) . ? Cl2 O3 1.407(4) 7_755 ? Cl2 O3 1.407(4) . ? Cl2 O2 1.410(6) . ? Cl2 O1 1.409(6) . ? N1 C8 1.488(5) . ? N1 C7 1.487(5) . ? N1 H1A 0.9601 . ? N2 C9 1.471(5) . ? N2 C10 1.474(6) . ? N2 H2A 0.9601 . ? C8 C9 1.509(8) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C7 C1 1.498(6) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C1 C2 1.388(6) . ? C1 C1 1.408(8) 7_655 ? C2 C3 1.368(6) . ? C2 H2 0.96 . ? C3 C3 1.378(10) 7_655 ? C3 H3 0.9601 . ? C10 C11 1.508(7) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C10 1.508(7) 7_655 ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N2 91.33(19) 7_655 . ? N2 Cu1 N1 175.76(12) 7_655 . ? N2 Cu1 N1 84.88(14) . . ? N2 Cu1 N1 84.88(14) 7_655 7_655 ? N2 Cu1 N1 175.76(12) . 7_655 ? N1 Cu1 N1 98.84(17) . 7_655 ? N2 Cu1 Cl1 94.49(10) 7_655 . ? N2 Cu1 Cl1 94.49(10) . . ? N1 Cu1 Cl1 87.72(9) . . ? N1 Cu1 Cl1 87.72(9) 7_655 . ? O3 Cl2 O3 112.2(6) 7_755 . ? O3 Cl2 O2 106.2(3) 7_755 . ? O3 Cl2 O2 106.2(3) . . ? O3 Cl2 O1 107.5(3) 7_755 . ? O3 Cl2 O1 107.5(3) . . ? O2 Cl2 O1 117.3(5) . . ? C8 N1 C7 110.4(3) . . ? C8 N1 Cu1 106.0(3) . . ? C7 N1 Cu1 121.6(2) . . ? C8 N1 H1A 107 . . ? C7 N1 H1A 104.6 . . ? Cu1 N1 H1A 106.4 . . ? C9 N2 C10 112.2(4) . . ? C9 N2 Cu1 107.2(3) . . ? C10 N2 Cu1 120.3(3) . . ? C9 N2 H2A 109 . . ? C10 N2 H2A 102.8 . . ? Cu1 N2 H2A 104.6 . . ? N1 C8 C9 107.9(3) . . ? N1 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? N1 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? N1 C7 C1 112.6(3) . . ? N1 C7 H7A 109.1 . . ? C1 C7 H7A 109.1 . . ? N1 C7 H7B 109.1 . . ? C1 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? N2 C9 C8 107.0(3) . . ? N2 C9 H9A 110.3 . . ? C8 C9 H9A 110.3 . . ? N2 C9 H9B 110.3 . . ? C8 C9 H9B 110.3 . . ? H9A C9 H9B 108.6 . . ? C2 C1 C1 118.1(3) . 7_655 ? C2 C1 C7 120.1(4) . . ? C1 C1 C7 121.7(2) 7_655 . ? C3 C2 C1 122.5(5) . . ? C3 C2 H2 118.1 . . ? C1 C2 H2 119.3 . . ? C2 C3 C3 119.3(3) . 7_655 ? C2 C3 H3 122 . . ? C3 C3 H3 118.7 7_655 . ? N2 C10 C11 111.9(5) . . ? N2 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? N2 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C10 C11 C10 114.0(7) . 7_655 ? C10 C11 H11A 108.7 . . ? C10 C11 H11A 108.7 7_655 . ? C10 C11 H11B 108.7 . . ? C10 C11 H11B 108.7 7_655 . ? H11A C11 H11B 107.6 . . ? data_ob232 _database_code_CSD 209939 _audit_creation_date 2003-05-26T18:00:27-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C15 H28 Cl2 N4 O Zn' _chemical_formula_weight 416.68 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1050(2) _cell_length_b 11.2190(3) _cell_length_c 12.2640(4) _cell_angle_alpha 98.2020(11) _cell_angle_beta 95.2080(11) _cell_angle_gamma 92.8280(13) _cell_volume 961.66(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.563 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_unetI/netI 0.0358 _diffrn_reflns_number 6918 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 4363 _reflns_number_gt 3514 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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_number_reflns 4363 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.048 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 0.877 _refine_ls_restrained_S_all 0.877 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.337 _refine_diff_density_min -0.86 _refine_diff_density_rms 0.095 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 0.41333(4) 0.25539(2) 0.80082(2) 0.04787(12) Uani 1 1 d . . . Cl2 Cl 0.04742(8) 0.21398(5) 0.62981(5) 0.05848(17) Uani 1 1 d . . . Cl1 Cl 0.66538(9) 0.27994(6) 0.94181(6) 0.06702(19) Uani 1 1 d . . . O1 O 0.0256(5) 0.9264(3) 0.6233(2) 0.0939(8) Uani 1 1 d . . . H100 H 1.007(6) -0.110(4) 0.560(4) 0.104(14) Uiso 1 1 d . . . H101 H 0.993(7) -0.010(4) 0.622(4) 0.116(18) Uiso 1 1 d . . . N4 N 0.5738(2) 0.25131(14) 0.66056(14) 0.0405(4) Uani 1 1 d . . . H4A H 0.7016 0.2662 0.6944 0.049 Uiso 1 1 d R . . N1 N 0.3318(3) 0.43805(17) 0.82143(17) 0.0503(4) Uani 1 1 d . . . H1A H 0.427(4) 0.474(2) 0.874(2) 0.050(7) Uiso 1 1 d . . . N2 N 0.1869(3) 0.2305(2) 0.90077(17) 0.0549(5) Uani 1 1 d . . . H2A H 0.092(5) 0.215(3) 0.851(3) 0.077(9) Uiso 1 1 d . . . C15 C 0.5417(4) 0.33676(19) 0.57927(19) 0.0518(5) Uani 1 1 d . . . H15A H 0.4072 0.3356 0.5563 0.065(8) Uiso 1 1 calc R . . H15B H 0.6055 0.3105 0.5142 0.081(9) Uiso 1 1 calc R . . C14 C 0.5503(3) 0.12504(18) 0.60318(18) 0.0466(5) Uani 1 1 d . . . H14A H 0.6519 0.1094 0.5564 0.058(7) Uiso 1 1 calc R . . H14B H 0.4311 0.1129 0.5565 0.041(6) Uiso 1 1 calc R . . C6 C 0.6139(3) 0.46432(19) 0.62736(19) 0.0478(5) Uani 1 1 d . . . N3 N 0.3956(3) 0.06456(17) 0.75525(17) 0.0474(4) Uani 1 1 d . . . H3A H 0.303(4) 0.052(2) 0.715(2) 0.052(7) Uiso 1 1 d . . . C13 C 0.5530(3) 0.03901(19) 0.6873(2) 0.0517(5) Uani 1 1 d . . . H13A H 0.5386 -0.0437 0.6502 0.061(7) Uiso 1 1 calc R . . H13B H 0.6725 0.05 0.7337 0.061(7) Uiso 1 1 calc R . . C5 C 0.7901(4) 0.5066(2) 0.6023(2) 0.0602(6) Uani 1 1 d . . . H5 H 0.8642 0.4537 0.5575 0.072 Uiso 1 1 d R . . C10 C 0.2093(4) 0.1380(3) 0.9732(2) 0.0692(7) Uani 1 1 d . . . H10A H 0.3285 0.1582 1.0171 0.083 Uiso 1 1 d R . . H10B H 0.1094 0.1381 1.021 0.083 Uiso 1 1 d R . . C1 C 0.5093(3) 0.54158(19) 0.6944(2) 0.0531(5) Uani 1 1 d . . . C7 C 0.3178(3) 0.5054(2) 0.7259(2) 0.0611(6) Uani 1 1 d . . . H7A H 0.2505 0.4523 0.665 0.073 Uiso 1 1 d R . . H7B H 0.2492 0.5763 0.742 0.073 Uiso 1 1 d R . . C8 C 0.1549(4) 0.4383(2) 0.8770(3) 0.0670(8) Uani 1 1 d . . . H8A H 0.1332 0.5174 0.9132 0.08 Uiso 1 1 d R . . H8B H 0.0513 0.4106 0.8219 0.08 Uiso 1 1 d R . . C4 C 0.8619(4) 0.6237(2) 0.6412(2) 0.0671(7) Uani 1 1 d . . . H4 H 0.982 0.6524 0.6215 0.081 Uiso 1 1 d R . . C12 C 0.3880(4) -0.0077(2) 0.8463(2) 0.0662(7) Uani 1 1 d . . . H12A H 0.3906 -0.0919 0.8182 0.079 Uiso 1 1 d R . . H12B H 0.4974 0.017 0.898 0.079 Uiso 1 1 d R . . C2 C 0.5854(4) 0.6583(2) 0.7339(2) 0.0652(7) Uani 1 1 d . . . H2 H 0.5164 0.7124 0.7809 0.078 Uiso 1 1 d R . . C9 C 0.1637(4) 0.3520(3) 0.9603(2) 0.0693(8) Uani 1 1 d . . . H9A H 0.0516 0.3536 0.9985 0.083 Uiso 1 1 d R . . H9B H 0.273 0.3731 1.0128 0.083 Uiso 1 1 d R . . C3 C 0.7596(4) 0.6999(2) 0.7078(2) 0.0689(7) Uani 1 1 d . . . H3 H 0.8091 0.7807 0.7356 0.083 Uiso 1 1 d R . . C11 C 0.2148(4) 0.0134(3) 0.9079(2) 0.0694(7) Uani 1 1 d . . . H11A H 0.2069 -0.0472 0.9555 0.083 Uiso 1 1 d R . . H11B H 0.1089 0.0012 0.8521 0.083 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.05216(18) 0.04588(17) 0.04626(17) 0.00366(11) 0.01128(12) 0.00730(11) Cl2 0.0546(3) 0.0538(3) 0.0626(4) -0.0027(3) -0.0010(3) 0.0047(2) Cl1 0.0543(3) 0.0790(4) 0.0628(4) 0.0101(3) -0.0125(3) -0.0106(3) O1 0.135(2) 0.0695(15) 0.0694(15) 0.0103(12) -0.0171(15) -0.0224(15) N4 0.0426(8) 0.0372(8) 0.0402(8) 0.0014(6) 0.0010(7) 0.0049(7) N1 0.0394(9) 0.0476(10) 0.0579(11) -0.0109(8) 0.0018(8) 0.0018(8) N2 0.0454(10) 0.0650(12) 0.0496(11) -0.0052(9) 0.0056(9) -0.0058(9) C15 0.0644(14) 0.0472(11) 0.0427(11) 0.0083(9) -0.0039(10) 0.0045(10) C14 0.0520(11) 0.0420(10) 0.0433(11) -0.0037(8) 0.0067(9) 0.0044(9) C6 0.0545(12) 0.0438(10) 0.0459(11) 0.0144(8) -0.0045(9) 0.0045(9) N3 0.0468(10) 0.0456(10) 0.0484(10) 0.0077(8) -0.0024(9) -0.0008(8) C13 0.0548(12) 0.0386(10) 0.0598(13) 0.0002(9) 0.0041(11) 0.0077(9) C5 0.0645(14) 0.0565(13) 0.0636(15) 0.0231(11) 0.0053(12) 0.0051(11) C10 0.0627(15) 0.093(2) 0.0515(14) 0.0133(13) 0.0092(12) -0.0155(14) C1 0.0569(13) 0.0399(10) 0.0605(13) 0.0099(9) -0.0098(11) 0.0051(9) C7 0.0538(13) 0.0481(12) 0.0786(17) 0.0036(11) -0.0062(12) 0.0153(10) C8 0.0487(12) 0.0580(14) 0.0860(19) -0.0245(13) 0.0156(13) 0.0062(11) C4 0.0628(14) 0.0639(15) 0.0780(18) 0.0327(13) -0.0052(13) -0.0061(12) C12 0.0753(17) 0.0577(14) 0.0673(16) 0.0224(12) 0.0003(14) -0.0035(13) C2 0.0774(17) 0.0418(12) 0.0741(17) 0.0077(11) -0.0061(14) 0.0087(11) C9 0.0530(13) 0.0834(18) 0.0640(16) -0.0210(14) 0.0226(12) -0.0082(12) C3 0.0791(17) 0.0467(12) 0.0777(18) 0.0185(12) -0.0156(15) -0.0112(12) C11 0.0723(16) 0.0732(17) 0.0631(15) 0.0224(13) 0.0029(13) -0.0206(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N3 2.1286(19) . ? Zn1 N2 2.1403(19) . ? Zn1 N1 2.1437(18) . ? Zn1 N4 2.1445(17) . ? Zn1 Cl1 2.3507(7) . ? N4 C14 1.484(2) . ? N4 C15 1.489(3) . ? N4 H4A 0.96 . ? N1 C7 1.481(3) . ? N1 C8 1.483(3) . ? N1 H1A 0.92(3) . ? N2 C10 1.465(4) . ? N2 C9 1.475(3) . ? N2 H2A 0.86(3) . ? C15 C6 1.514(3) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C14 C13 1.510(3) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C6 C5 1.393(4) . ? C6 C1 1.396(3) . ? N3 C13 1.470(3) . ? N3 C12 1.474(3) . ? N3 H3A 0.78(3) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C5 C4 1.387(4) . ? C5 H5 0.9599 . ? C10 C11 1.512(4) . ? C10 H10A 0.96 . ? C10 H10B 0.9599 . ? C1 C2 1.394(3) . ? C1 C7 1.500(4) . ? C7 H7A 0.9601 . ? C7 H7B 0.96 . ? C8 C9 1.504(4) . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C4 C3 1.377(4) . ? C4 H4 0.96 . ? C12 C11 1.512(4) . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C2 C3 1.382(4) . ? C2 H2 0.96 . ? C9 H9A 0.9599 . ? C9 H9B 0.96 . ? C3 H3 0.96 . ? C11 H11A 0.96 . ? C11 H11B 0.9601 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Zn1 N2 87.13(8) . . ? N3 Zn1 N1 160.07(8) . . ? N2 Zn1 N1 82.75(8) . . ? N3 Zn1 N4 83.15(7) . . ? N2 Zn1 N4 161.65(8) . . ? N1 Zn1 N4 101.52(7) . . ? N3 Zn1 Cl1 100.72(6) . . ? N2 Zn1 Cl1 98.21(6) . . ? N1 Zn1 Cl1 97.70(6) . . ? N4 Zn1 Cl1 98.87(5) . . ? C14 N4 C15 110.16(16) . . ? C14 N4 Zn1 105.66(12) . . ? C15 N4 Zn1 121.16(13) . . ? C14 N4 H4A 108.5 . . ? C15 N4 H4A 108.1 . . ? Zn1 N4 H4A 102.6 . . ? C7 N1 C8 112.1(2) . . ? C7 N1 Zn1 120.20(14) . . ? C8 N1 Zn1 106.44(15) . . ? C7 N1 H1A 109.8(16) . . ? C8 N1 H1A 106.9(16) . . ? Zn1 N1 H1A 100.2(16) . . ? C10 N2 C9 113.8(2) . . ? C10 N2 Zn1 115.93(16) . . ? C9 N2 Zn1 104.69(15) . . ? C10 N2 H2A 113(2) . . ? C9 N2 H2A 106(2) . . ? Zn1 N2 H2A 101(2) . . ? N4 C15 C6 111.88(18) . . ? N4 C15 H15A 109.2 . . ? C6 C15 H15A 109.2 . . ? N4 C15 H15B 109.2 . . ? C6 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? N4 C14 C13 109.82(17) . . ? N4 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? N4 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C5 C6 C1 118.9(2) . . ? C5 C6 C15 118.6(2) . . ? C1 C6 C15 122.5(2) . . ? C13 N3 C12 114.03(19) . . ? C13 N3 Zn1 105.27(13) . . ? C12 N3 Zn1 116.37(16) . . ? C13 N3 H3A 106.5(19) . . ? C12 N3 H3A 110(2) . . ? Zn1 N3 H3A 103.4(19) . . ? N3 C13 C14 107.93(17) . . ? N3 C13 H13A 110.1 . . ? C14 C13 H13A 110.1 . . ? N3 C13 H13B 110.1 . . ? C14 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? C6 C5 C4 121.4(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119 . . ? N2 C10 C11 111.9(2) . . ? N2 C10 H10A 106.2 . . ? C11 C10 H10A 108.7 . . ? N2 C10 H10B 111 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C2 C1 C6 118.7(2) . . ? C2 C1 C7 118.1(2) . . ? C6 C1 C7 123.2(2) . . ? N1 C7 C1 111.82(19) . . ? N1 C7 H7A 106.8 . . ? C1 C7 H7A 109 . . ? N1 C7 H7B 110.7 . . ? C1 C7 H7B 109 . . ? H7A C7 H7B 109.5 . . ? N1 C8 C9 109.9(2) . . ? N1 C8 H8A 111.8 . . ? C9 C8 H8A 109.5 . . ? N1 C8 H8B 108.1 . . ? C9 C8 H8B 107.9 . . ? H8A C8 H8B 109.5 . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 120.6 . . ? N3 C12 C11 112.3(2) . . ? N3 C12 H12A 110.1 . . ? C11 C12 H12A 109.7 . . ? N3 C12 H12B 107.6 . . ? C11 C12 H12B 107.6 . . ? H12A C12 H12B 109.5 . . ? C3 C2 C1 122.0(3) . . ? C3 C2 H2 118 . . ? C1 C2 H2 120 . . ? N2 C9 C8 108.0(2) . . ? N2 C9 H9A 111.5 . . ? C8 C9 H9A 110.5 . . ? N2 C9 H9B 107.4 . . ? C8 C9 H9B 109.9 . . ? H9A C9 H9B 109.5 . . ? C4 C3 C2 119.1(2) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.7 . . ? C12 C11 C10 115.5(2) . . ? C12 C11 H11A 107.2 . . ? C10 C11 H11A 110.6 . . ? C12 C11 H11B 105.6 . . ? C10 C11 H11B 108.2 . . ? H11A C11 H11B 109.5 . . ?