# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 N8 O5 Zn' _chemical_formula_weight 477.75 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 monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 9.0396(18) _cell_length_b 10.003(2) _cell_length_c 19.505(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.80(3) _cell_angle_gamma 90.00 _cell_volume 1763.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12015 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 27.49 _exptl_crystal_description columnar _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.799 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 1.448 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_T_max 0.865 _exptl_absorpt_process_details Process-auto _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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16121 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.0582 _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 -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4016 _reflns_number_gt 2923 _reflns_threshold_expression >2sigma(I) _computing_data_collection Process-auto _computing_cell_refinement Process-auto _computing_data_reduction Process-auto _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0623P)^2^+1.3943P] 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 4016 _refine_ls_number_parameters 304 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1279 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.43177(5) -0.36826(4) 0.05318(2) 0.02580(14) Uani 1 1 d . . . N1 N 0.2287(3) -0.2861(3) 0.04763(15) 0.0256(6) Uani 1 1 d . . . N2 N 0.1210(3) -0.3287(3) -0.00023(16) 0.0281(7) Uani 1 1 d . . . H2A H 0.1439 -0.3965 -0.0250 0.034 Uiso 1 1 calc R . . N3 N 0.4325(3) 0.2709(3) 0.32447(16) 0.0302(7) Uani 1 1 d . . . H3A H 0.5158 0.3123 0.3234 0.036 Uiso 1 1 calc R . . N4 N 0.4128(3) 0.1845(3) 0.37905(15) 0.0248(6) Uani 1 1 d . . . N5 N -0.2690(4) 0.2278(4) 0.16212(19) 0.0429(9) Uani 1 1 d . . . N6 N -0.2975(5) 0.3308(4) 0.2070(2) 0.0514(10) Uani 1 1 d . . . H6A H -0.2362 0.3480 0.2400 0.062 Uiso 1 1 calc R . . H6B H -0.3766 0.3778 0.2021 0.062 Uiso 1 1 calc R . . N7 N 0.4966(4) -0.3444(3) -0.04757(17) 0.0294(7) Uani 1 1 d D . . N8 N 0.6093(3) -0.4316(3) -0.07252(17) 0.0275(7) Uani 1 1 d D . . O1 O 0.2931(3) -0.1459(3) 0.13257(14) 0.0330(6) Uani 1 1 d . . . O2 O -0.0961(3) -0.3218(3) -0.05663(14) 0.0333(6) Uani 1 1 d . . . O3 O 0.3708(3) 0.3757(3) 0.22597(15) 0.0396(7) Uani 1 1 d . . . O4 O 0.2694(3) 0.0409(3) 0.43480(13) 0.0301(6) Uani 1 1 d . . . C1 C 0.0165(4) -0.0174(4) 0.12760(18) 0.0262(8) Uani 1 1 d . . . H1A H 0.0849 0.0083 0.1611 0.031 Uiso 1 1 calc R . . C2 C -0.1194(4) 0.0491(3) 0.12270(18) 0.0225(7) Uani 1 1 d . . . C3 C -0.2220(4) 0.0047(4) 0.07262(19) 0.0268(8) Uani 1 1 d . . . H3B H -0.3140 0.0459 0.0690 0.032 Uiso 1 1 calc R . . C4 C -0.1883(4) -0.0984(4) 0.02899(19) 0.0277(8) Uani 1 1 d . . . H4B H -0.2573 -0.1249 -0.0041 0.033 Uiso 1 1 calc R . . C5 C -0.0514(4) -0.1644(3) 0.03362(18) 0.0221(7) Uani 1 1 d . . . C6 C 0.0510(4) -0.1215(3) 0.08327(17) 0.0217(7) Uani 1 1 d . . . C7 C -0.0128(4) -0.2759(4) -0.01156(18) 0.0237(7) Uani 1 1 d . . . C8 C 0.1972(4) -0.1860(4) 0.08871(18) 0.0234(7) Uani 1 1 d . . . C9 C 0.0861(4) 0.2407(3) 0.22612(18) 0.0240(7) Uani 1 1 d . . . H9A H 0.1036 0.2952 0.1885 0.029 Uiso 1 1 calc R . . C10 C -0.0470(4) 0.1716(3) 0.23079(17) 0.0221(7) Uani 1 1 d . . . C11 C -0.0751(4) 0.0955(4) 0.28877(18) 0.0263(8) Uani 1 1 d . . . H11A H -0.1664 0.0537 0.2931 0.032 Uiso 1 1 calc R . . C12 C 0.0311(4) 0.0809(4) 0.34020(18) 0.0259(7) Uani 1 1 d . . . H12A H 0.0118 0.0286 0.3785 0.031 Uiso 1 1 calc R . . C13 C 0.1670(4) 0.1453(3) 0.33418(17) 0.0222(7) Uani 1 1 d . . . C14 C 0.1932(4) 0.2284(3) 0.27788(18) 0.0237(7) Uani 1 1 d . . . C15 C 0.3372(4) 0.2975(4) 0.27307(19) 0.0284(8) Uani 1 1 d . . . C16 C 0.2847(4) 0.1213(3) 0.38533(17) 0.0231(7) Uani 1 1 d . . . C17 C -0.1516(4) 0.1600(4) 0.17057(18) 0.0235(7) Uani 1 1 d . . . OW1 O 0.4164(5) 0.1093(5) 0.1234(2) 0.0738(13) Uani 1 1 d . . . H06 H 0.373(6) 0.040(6) 0.128(3) 0.060(18) Uiso 1 1 d . . . H05 H 0.314(10) 0.167(8) 0.124(4) 0.13(3) Uiso 1 1 d . . . H02 H 0.427(5) -0.357(4) -0.066(2) 0.019(11) Uiso 1 1 d . . . H01 H 0.511(4) -0.267(4) -0.060(2) 0.024(11) Uiso 1 1 d . . . H04 H 0.635(4) -0.417(4) -0.116(2) 0.018(9) Uiso 1 1 d . . . H03 H 0.695(6) -0.414(5) -0.057(2) 0.042(13) 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 Zn1 0.0215(2) 0.0307(2) 0.0250(2) -0.00418(18) -0.00684(15) 0.00244(19) N1 0.0208(15) 0.0290(15) 0.0269(16) -0.0041(12) -0.0063(12) 0.0029(13) N2 0.0266(16) 0.0295(16) 0.0280(16) -0.0090(13) -0.0046(13) 0.0011(13) N3 0.0188(15) 0.0405(18) 0.0310(17) 0.0113(14) -0.0086(12) -0.0087(14) N4 0.0180(14) 0.0321(15) 0.0241(15) 0.0068(12) -0.0074(11) -0.0027(13) N5 0.035(2) 0.054(2) 0.039(2) -0.0088(17) -0.0046(16) 0.0107(18) N6 0.045(2) 0.062(3) 0.047(2) -0.0119(19) -0.0045(18) 0.017(2) N7 0.030(2) 0.0295(18) 0.0283(17) 0.0008(14) -0.0080(14) 0.0010(15) N8 0.0233(16) 0.0343(17) 0.0250(17) 0.0008(13) -0.0026(13) -0.0031(14) O1 0.0230(13) 0.0358(14) 0.0399(15) -0.0093(12) -0.0141(11) 0.0055(11) O2 0.0260(14) 0.0430(15) 0.0305(14) -0.0104(12) -0.0074(11) -0.0022(12) O3 0.0273(14) 0.0537(18) 0.0378(16) 0.0229(14) -0.0049(12) -0.0063(14) O4 0.0267(13) 0.0386(14) 0.0250(13) 0.0091(11) -0.0052(10) -0.0019(12) C1 0.0188(17) 0.0353(19) 0.0244(18) 0.0000(15) -0.0080(13) -0.0003(16) C2 0.0195(17) 0.0262(17) 0.0219(17) 0.0011(13) -0.0018(13) 0.0009(14) C3 0.0159(16) 0.0355(19) 0.0289(19) -0.0019(15) -0.0061(13) 0.0053(15) C4 0.0197(17) 0.0346(19) 0.0284(19) -0.0020(15) -0.0102(14) -0.0003(16) C5 0.0184(17) 0.0255(17) 0.0224(17) 0.0023(13) -0.0045(13) -0.0026(14) C6 0.0165(16) 0.0257(16) 0.0229(16) -0.0005(14) -0.0050(13) 0.0029(14) C7 0.0204(17) 0.0282(17) 0.0223(17) 0.0014(14) -0.0034(13) -0.0020(15) C8 0.0180(17) 0.0267(16) 0.0253(18) 0.0009(14) -0.0030(13) 0.0011(15) C9 0.0241(18) 0.0257(17) 0.0223(17) 0.0021(13) -0.0027(14) 0.0009(15) C10 0.0175(16) 0.0259(16) 0.0228(17) -0.0044(13) -0.0057(13) 0.0053(14) C11 0.0194(17) 0.0313(18) 0.0281(19) -0.0029(15) -0.0044(14) 0.0000(15) C12 0.0225(17) 0.0314(18) 0.0237(18) 0.0038(14) -0.0003(14) -0.0003(16) C13 0.0201(16) 0.0251(16) 0.0212(16) -0.0018(13) -0.0055(13) 0.0022(15) C14 0.0176(17) 0.0284(17) 0.0248(17) -0.0041(14) -0.0049(13) 0.0016(15) C15 0.0238(18) 0.036(2) 0.0248(18) 0.0044(15) -0.0036(14) -0.0010(17) C16 0.0221(17) 0.0239(16) 0.0230(17) -0.0001(14) -0.0045(13) 0.0033(15) C17 0.0135(16) 0.0334(18) 0.0234(17) -0.0011(14) -0.0043(13) 0.0040(14) OW1 0.075(3) 0.054(2) 0.093(3) 0.014(2) -0.004(2) -0.022(2) _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 N4 1.987(3) 2_645 ? Zn1 N1 2.013(3) . ? Zn1 N8 2.071(3) 3_645 ? Zn1 N7 2.072(3) . ? N1 C8 1.316(5) . ? N1 N2 1.405(4) . ? N2 C7 1.335(5) . ? N3 C15 1.339(5) . ? N3 N4 1.384(4) . ? N4 C16 1.326(5) . ? N4 Zn1 1.987(3) 2_655 ? N5 C17 1.268(5) . ? N5 N6 1.379(5) . ? N7 N8 1.4319(11) . ? N8 Zn1 2.071(3) 3_645 ? O1 C8 1.274(4) . ? O2 C7 1.238(4) . ? O3 C15 1.247(4) . ? O4 C16 1.265(4) . ? C1 C6 1.391(5) . ? C1 C2 1.399(5) . ? C2 C3 1.409(5) . ? C2 C17 1.481(5) . ? C3 C4 1.374(5) . ? C4 C5 1.405(5) . ? C5 C6 1.398(5) . ? C5 C7 1.466(5) . ? C6 C8 1.473(5) . ? C9 C10 1.392(5) . ? C9 C14 1.394(5) . ? C10 C11 1.390(5) . ? C10 C17 1.502(5) . ? C11 C12 1.387(5) . ? C12 C13 1.393(5) . ? C13 C14 1.400(5) . ? C13 C16 1.468(5) . ? C14 C15 1.477(5) . ? 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 N4 Zn1 N1 124.28(12) 2_645 . ? N4 Zn1 N8 105.21(13) 2_645 3_645 ? N1 Zn1 N8 103.81(12) . 3_645 ? N4 Zn1 N7 113.18(14) 2_645 . ? N1 Zn1 N7 99.89(12) . . ? N8 Zn1 N7 109.75(12) 3_645 . ? C8 N1 N2 118.8(3) . . ? C8 N1 Zn1 118.9(2) . . ? N2 N1 Zn1 122.3(2) . . ? C7 N2 N1 127.4(3) . . ? C15 N3 N4 127.7(3) . . ? C16 N4 N3 119.3(3) . . ? C16 N4 Zn1 115.0(2) . 2_655 ? N3 N4 Zn1 125.5(2) . 2_655 ? C17 N5 N6 118.7(4) . . ? N8 N7 Zn1 117.6(2) . . ? N7 N8 Zn1 113.4(2) . 3_645 ? C6 C1 C2 121.2(3) . . ? C1 C2 C3 117.7(3) . . ? C1 C2 C17 119.6(3) . . ? C3 C2 C17 122.7(3) . . ? C4 C3 C2 121.1(3) . . ? C3 C4 C5 121.0(3) . . ? C6 C5 C4 118.3(3) . . ? C6 C5 C7 119.3(3) . . ? C4 C5 C7 122.4(3) . . ? C1 C6 C5 120.6(3) . . ? C1 C6 C8 119.5(3) . . ? C5 C6 C8 120.0(3) . . ? O2 C7 N2 120.8(3) . . ? O2 C7 C5 124.2(3) . . ? N2 C7 C5 115.1(3) . . ? O1 C8 N1 119.8(3) . . ? O1 C8 C6 120.7(3) . . ? N1 C8 C6 119.4(3) . . ? C10 C9 C14 120.1(3) . . ? C11 C10 C9 119.6(3) . . ? C11 C10 C17 118.3(3) . . ? C9 C10 C17 121.5(3) . . ? C12 C11 C10 120.9(3) . . ? C11 C12 C13 119.5(3) . . ? C12 C13 C14 120.0(3) . . ? C12 C13 C16 119.9(3) . . ? C14 C13 C16 120.1(3) . . ? C9 C14 C13 119.8(3) . . ? C9 C14 C15 121.1(3) . . ? C13 C14 C15 119.1(3) . . ? O3 C15 N3 121.0(3) . . ? O3 C15 C14 124.3(3) . . ? N3 C15 C14 114.7(3) . . ? O4 C16 N4 118.6(3) . . ? O4 C16 C13 122.4(3) . . ? N4 C16 C13 119.0(3) . . ? N5 C17 C2 119.3(3) . . ? N5 C17 C10 125.2(3) . . ? C2 C17 C10 115.1(3) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.609 _refine_diff_density_min -0.459 _refine_diff_density_rms 0.104 _database_code_depnum_ccdc_archive 'CCDC 951026' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H14 N4 O4 Zn' _chemical_formula_weight 487.78 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9193(16) _cell_length_b 11.378(2) _cell_length_c 11.607(2) _cell_angle_alpha 67.29(3) _cell_angle_beta 88.38(3) _cell_angle_gamma 81.81(3) _cell_volume 954.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7950 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 27.51 _exptl_crystal_description columnar _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.697 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.331 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.841 _exptl_absorpt_correction_T_max 0.875 _exptl_absorpt_process_details Process-auto _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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9046 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0730 _diffrn_reflns_limit_h_min -10 _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 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4175 _reflns_number_gt 3508 _reflns_threshold_expression >2sigma(I) _computing_data_collection Process-auto _computing_cell_refinement Process-auto _computing_data_reduction Process-auto _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0639P)^2^+11.5579P] 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 4175 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0913 _refine_ls_R_factor_gt 0.0806 _refine_ls_wR_factor_ref 0.2080 _refine_ls_wR_factor_gt 0.2023 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 0.36199(8) 0.37072(7) 0.03488(6) 0.0139(2) Uani 1 1 d . . . O1 O 0.5732(5) 0.5029(4) 0.1256(4) 0.0169(8) Uani 1 1 d . . . O2 O -0.0393(6) 0.5179(5) 0.3354(4) 0.0237(10) Uani 1 1 d . . . O3 O -0.4433(5) 0.2336(4) 0.1082(4) 0.0213(9) Uani 1 1 d . . . O4 O 0.2075(5) 0.2856(5) -0.0170(4) 0.0209(9) Uani 1 1 d . . . N1 N 0.3058(6) 0.4577(5) 0.1535(5) 0.0148(10) Uani 1 1 d . . . N2 N 0.1484(6) 0.4619(5) 0.2108(5) 0.0170(10) Uani 1 1 d . . . H2A H 0.0716 0.4257 0.1916 0.020 Uiso 1 1 calc R . . N3 N -0.1896(6) 0.3015(5) 0.1186(5) 0.0170(10) Uani 1 1 d . . . H3A H -0.2356 0.3313 0.1717 0.020 Uiso 1 1 calc R . . N4 N -0.0226(6) 0.3213(5) 0.0914(5) 0.0163(10) Uani 1 1 d . . . C1 C 0.3306(9) 0.7334(6) 0.5422(6) 0.0225(13) Uani 1 1 d . . . H1A H 0.2253 0.7386 0.5788 0.027 Uiso 1 1 calc R . . C2 C 0.4632(10) 0.7805(7) 0.5756(7) 0.0280(15) Uani 1 1 d . . . H2B H 0.4473 0.8171 0.6349 0.034 Uiso 1 1 calc R . . C3 C 0.6218(9) 0.7739(7) 0.5210(6) 0.0256(14) Uani 1 1 d . . . H3B H 0.7100 0.8068 0.5443 0.031 Uiso 1 1 calc R . . C4 C 0.6506(9) 0.7198(6) 0.4336(6) 0.0214(13) Uani 1 1 d . . . H4B H 0.7576 0.7154 0.3991 0.026 Uiso 1 1 calc R . . C5 C 0.5149(8) 0.6705(6) 0.3962(5) 0.0171(12) Uani 1 1 d . . . C6 C 0.3532(8) 0.6768(6) 0.4520(5) 0.0171(12) Uani 1 1 d . . . C7 C 0.2185(7) 0.6274(6) 0.4161(5) 0.0155(11) Uani 1 1 d . . . H7A H 0.1121 0.6322 0.4514 0.019 Uiso 1 1 calc R . . C8 C 0.2446(8) 0.5720(6) 0.3290(5) 0.0157(11) Uani 1 1 d . . . C9 C 0.4076(7) 0.5663(6) 0.2742(5) 0.0135(11) Uani 1 1 d . . . C10 C 0.5393(8) 0.6147(6) 0.3079(5) 0.0155(11) Uani 1 1 d . . . H10A H 0.6450 0.6101 0.2717 0.019 Uiso 1 1 calc R . . C11 C 0.4299(7) 0.5091(6) 0.1810(5) 0.0130(11) Uani 1 1 d . . . C12 C 0.1061(7) 0.5173(6) 0.2935(5) 0.0167(11) Uani 1 1 d . . . C13 C -0.3168(9) 0.0121(6) -0.2067(6) 0.0249(14) Uani 1 1 d . . . H13A H -0.4301 0.0024 -0.1876 0.030 Uiso 1 1 calc R . . C14 C -0.2381(11) -0.0347(7) -0.2880(7) 0.0319(16) Uani 1 1 d . . . H14A H -0.2976 -0.0774 -0.3239 0.038 Uiso 1 1 calc R . . C15 C -0.0652(10) -0.0196(7) -0.3196(7) 0.0286(15) Uani 1 1 d . . . H15A H -0.0129 -0.0529 -0.3754 0.034 Uiso 1 1 calc R . . C16 C 0.0233(10) 0.0427(6) -0.2692(6) 0.0251(14) Uani 1 1 d . . . H16A H 0.1360 0.0520 -0.2907 0.030 Uiso 1 1 calc R . . C17 C -0.0540(8) 0.0941(6) -0.1835(6) 0.0194(12) Uani 1 1 d . . . C18 C -0.2257(8) 0.0765(6) -0.1503(6) 0.0197(12) Uani 1 1 d . . . C19 C -0.3023(8) 0.1266(6) -0.0649(6) 0.0189(12) Uani 1 1 d . . . H19A H -0.4157 0.1186 -0.0445 0.023 Uiso 1 1 calc R . . C20 C -0.2107(7) 0.1874(6) -0.0114(5) 0.0156(11) Uani 1 1 d . . . C21 C -0.0404(7) 0.2047(6) -0.0435(6) 0.0160(11) Uani 1 1 d . . . C22 C 0.0376(8) 0.1583(6) -0.1284(5) 0.0163(11) Uani 1 1 d . . . H22A H 0.1502 0.1691 -0.1494 0.020 Uiso 1 1 calc R . . C23 C -0.2891(8) 0.2430(6) 0.0744(6) 0.0159(11) Uani 1 1 d . . . C24 C 0.0501(7) 0.2741(6) 0.0133(5) 0.0152(11) 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 0.0086(3) 0.0209(4) 0.0164(3) -0.0112(3) 0.0021(2) -0.0044(2) O1 0.0113(19) 0.022(2) 0.019(2) -0.0091(17) 0.0028(16) -0.0050(16) O2 0.014(2) 0.039(3) 0.021(2) -0.014(2) 0.0059(17) -0.0086(19) O3 0.011(2) 0.027(2) 0.028(2) -0.012(2) 0.0022(17) -0.0058(18) O4 0.014(2) 0.030(2) 0.024(2) -0.014(2) 0.0031(17) -0.0094(18) N1 0.008(2) 0.024(3) 0.015(2) -0.009(2) 0.0023(18) -0.0060(19) N2 0.011(2) 0.027(3) 0.019(2) -0.014(2) 0.0058(19) -0.009(2) N3 0.011(2) 0.025(3) 0.022(3) -0.015(2) 0.0021(19) -0.006(2) N4 0.007(2) 0.022(3) 0.020(2) -0.008(2) -0.0007(18) -0.0034(19) C1 0.028(3) 0.024(3) 0.018(3) -0.012(3) 0.000(2) 0.001(3) C2 0.037(4) 0.027(3) 0.026(3) -0.019(3) -0.002(3) 0.000(3) C3 0.030(4) 0.025(3) 0.027(3) -0.014(3) -0.005(3) -0.004(3) C4 0.023(3) 0.022(3) 0.024(3) -0.013(3) 0.000(2) -0.004(3) C5 0.021(3) 0.014(3) 0.014(3) -0.004(2) -0.004(2) -0.001(2) C6 0.021(3) 0.014(3) 0.014(3) -0.004(2) -0.001(2) 0.001(2) C7 0.010(3) 0.022(3) 0.015(3) -0.008(2) 0.002(2) -0.002(2) C8 0.015(3) 0.014(3) 0.015(3) -0.003(2) -0.003(2) 0.001(2) C9 0.014(3) 0.015(3) 0.012(2) -0.006(2) 0.000(2) -0.002(2) C10 0.017(3) 0.015(3) 0.016(3) -0.008(2) 0.001(2) -0.004(2) C11 0.010(2) 0.018(3) 0.012(2) -0.006(2) 0.004(2) -0.005(2) C12 0.012(3) 0.022(3) 0.016(3) -0.006(2) 0.002(2) -0.005(2) C13 0.031(4) 0.020(3) 0.028(3) -0.013(3) -0.004(3) -0.009(3) C14 0.048(5) 0.028(4) 0.025(3) -0.014(3) -0.002(3) -0.012(3) C15 0.043(4) 0.020(3) 0.028(3) -0.014(3) 0.003(3) -0.005(3) C16 0.033(4) 0.020(3) 0.020(3) -0.005(3) 0.001(3) -0.006(3) C17 0.027(3) 0.012(3) 0.019(3) -0.006(2) -0.002(2) -0.004(2) C18 0.023(3) 0.017(3) 0.019(3) -0.007(2) -0.005(2) 0.001(2) C19 0.017(3) 0.017(3) 0.023(3) -0.006(2) -0.003(2) -0.005(2) C20 0.013(3) 0.018(3) 0.015(3) -0.005(2) -0.001(2) -0.001(2) C21 0.012(3) 0.015(3) 0.020(3) -0.006(2) -0.004(2) 0.000(2) C22 0.017(3) 0.014(3) 0.016(3) -0.003(2) -0.001(2) -0.004(2) C23 0.015(3) 0.013(3) 0.019(3) -0.006(2) -0.003(2) -0.001(2) C24 0.010(3) 0.018(3) 0.017(3) -0.005(2) -0.003(2) -0.004(2) _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 O4 1.905(4) . ? Zn1 O1 1.972(4) 2_665 ? Zn1 O3 1.974(5) 1_655 ? Zn1 N1 1.992(5) . ? O1 C11 1.295(7) . ? O1 Zn1 1.972(4) 2_665 ? O2 C12 1.237(7) . ? O3 C23 1.279(7) . ? O3 Zn1 1.974(5) 1_455 ? O4 C24 1.296(7) . ? N1 C11 1.317(7) . ? N1 N2 1.400(7) . ? N2 C12 1.349(8) . ? N2 H2A 0.8600 . ? N3 C23 1.329(7) . ? N3 N4 1.381(7) . ? N3 H3A 0.8600 . ? N4 C24 1.303(8) . ? C1 C2 1.372(10) . ? C1 C6 1.421(8) . ? C1 H1A 0.9300 . ? C2 C3 1.396(10) . ? C2 H2B 0.9300 . ? C3 C4 1.373(9) . ? C3 H3B 0.9300 . ? C4 C5 1.431(8) . ? C4 H4B 0.9300 . ? C5 C10 1.395(8) . ? C5 C6 1.424(9) . ? C6 C7 1.415(8) . ? C7 C8 1.380(8) . ? C7 H7A 0.9300 . ? C8 C9 1.427(8) . ? C8 C12 1.476(8) . ? C9 C10 1.378(8) . ? C9 C11 1.457(8) . ? C10 H10A 0.9300 . ? C13 C14 1.350(10) . ? C13 C18 1.427(8) . ? C13 H13A 0.9300 . ? C14 C15 1.424(11) . ? C14 H14A 0.9300 . ? C15 C16 1.349(10) . ? C15 H15A 0.9300 . ? C16 C17 1.420(9) . ? C16 H16A 0.9300 . ? C17 C22 1.416(8) . ? C17 C18 1.424(9) . ? C18 C19 1.407(9) . ? C19 C20 1.376(8) . ? C19 H19A 0.9300 . ? C20 C21 1.410(8) . ? C20 C23 1.454(8) . ? C21 C22 1.381(8) . ? C21 C24 1.470(8) . ? C22 H22A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Zn1 O1 102.36(19) . 2_665 ? O4 Zn1 O3 102.9(2) . 1_655 ? O1 Zn1 O3 109.64(18) 2_665 1_655 ? O4 Zn1 N1 124.34(19) . . ? O1 Zn1 N1 109.21(19) 2_665 . ? O3 Zn1 N1 107.7(2) 1_655 . ? C11 O1 Zn1 126.8(4) . 2_665 ? C23 O3 Zn1 124.2(4) . 1_455 ? C24 O4 Zn1 128.6(4) . . ? C11 N1 N2 119.9(5) . . ? C11 N1 Zn1 116.0(4) . . ? N2 N1 Zn1 124.0(4) . . ? C12 N2 N1 126.0(5) . . ? C12 N2 H2A 117.0 . . ? N1 N2 H2A 117.0 . . ? C23 N3 N4 129.1(5) . . ? C23 N3 H3A 115.5 . . ? N4 N3 H3A 115.5 . . ? C24 N4 N3 116.1(5) . . ? C2 C1 C6 120.4(6) . . ? C2 C1 H1A 119.8 . . ? C6 C1 H1A 119.8 . . ? C1 C2 C3 120.4(6) . . ? C1 C2 H2B 119.8 . . ? C3 C2 H2B 119.8 . . ? C4 C3 C2 121.5(6) . . ? C4 C3 H3B 119.2 . . ? C2 C3 H3B 119.2 . . ? C3 C4 C5 119.5(6) . . ? C3 C4 H4B 120.3 . . ? C5 C4 H4B 120.3 . . ? C10 C5 C6 119.7(6) . . ? C10 C5 C4 121.2(6) . . ? C6 C5 C4 119.1(5) . . ? C7 C6 C1 121.5(6) . . ? C7 C6 C5 119.4(5) . . ? C1 C6 C5 119.0(6) . . ? C8 C7 C6 120.2(5) . . ? C8 C7 H7A 119.9 . . ? C6 C7 H7A 119.9 . . ? C7 C8 C9 119.6(5) . . ? C7 C8 C12 120.5(5) . . ? C9 C8 C12 119.8(5) . . ? C10 C9 C8 120.7(5) . . ? C10 C9 C11 121.2(5) . . ? C8 C9 C11 118.2(5) . . ? C9 C10 C5 120.3(6) . . ? C9 C10 H10A 119.8 . . ? C5 C10 H10A 119.8 . . ? O1 C11 N1 117.6(5) . . ? O1 C11 C9 121.6(5) . . ? N1 C11 C9 120.7(5) . . ? O2 C12 N2 120.1(6) . . ? O2 C12 C8 124.7(6) . . ? N2 C12 C8 115.2(5) . . ? C14 C13 C18 119.8(7) . . ? C14 C13 H13A 120.1 . . ? C18 C13 H13A 120.1 . . ? C13 C14 C15 121.0(7) . . ? C13 C14 H14A 119.5 . . ? C15 C14 H14A 119.5 . . ? C16 C15 C14 120.5(7) . . ? C16 C15 H15A 119.7 . . ? C14 C15 H15A 119.7 . . ? C15 C16 C17 120.7(7) . . ? C15 C16 H16A 119.7 . . ? C17 C16 H16A 119.7 . . ? C22 C17 C16 121.5(6) . . ? C22 C17 C18 119.9(6) . . ? C16 C17 C18 118.6(6) . . ? C19 C18 C17 118.8(6) . . ? C19 C18 C13 121.8(6) . . ? C17 C18 C13 119.4(6) . . ? C20 C19 C18 120.4(6) . . ? C20 C19 H19A 119.8 . . ? C18 C19 H19A 119.8 . . ? C19 C20 C21 121.1(6) . . ? C19 C20 C23 121.2(6) . . ? C21 C20 C23 117.6(5) . . ? C22 C21 C20 119.8(5) . . ? C22 C21 C24 121.3(5) . . ? C20 C21 C24 118.9(5) . . ? C21 C22 C17 120.0(6) . . ? C21 C22 H22A 120.0 . . ? C17 C22 H22A 120.0 . . ? O3 C23 N3 121.6(5) . . ? O3 C23 C20 122.4(5) . . ? N3 C23 C20 116.1(5) . . ? O4 C24 N4 121.0(5) . . ? O4 C24 C21 116.8(5) . . ? N4 C24 C21 122.2(5) . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 2.923 _refine_diff_density_min -0.918 _refine_diff_density_rms 0.173 _database_code_depnum_ccdc_archive 'CCDC 951027' ####################################################################### # # 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_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H11 N4 O4.50' _chemical_formula_weight 331.29 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 monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 5.8217(5) _cell_length_b 15.0795(9) _cell_length_c 16.8686(12) _cell_angle_alpha 90.00 _cell_angle_beta 95.602(5) _cell_angle_gamma 90.00 _cell_volume 1473.79(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 792 _cell_measurement_theta_min 2.4264 _cell_measurement_theta_max 21.5947 _exptl_crystal_description columnar _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 8082 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 25.13 _reflns_number_total 2563 _reflns_number_gt 1422 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMAR' _computing_cell_refinement 'Bruker SMAR' _computing_data_reduction 'Bruker SMAR' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1113P)^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 2563 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1125 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.1945 _refine_ls_wR_factor_gt 0.1614 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _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 C1 C 0.6161(7) 0.4753(2) 0.7795(2) 0.0531(10) Uani 1 1 d . . . H1A H 0.6223 0.5095 0.8255 0.064 Uiso 1 1 calc R . . C2 C 0.7777(7) 0.4124(3) 0.7714(2) 0.0578(11) Uani 1 1 d . . . H2A H 0.9013 0.4062 0.8104 0.069 Uiso 1 1 calc R . . C3 C 0.7601(7) 0.3568(3) 0.7052(2) 0.0535(10) Uani 1 1 d . . . H3A H 0.8696 0.3124 0.7017 0.064 Uiso 1 1 calc R . . C4 C 0.5854(6) 0.3657(2) 0.6451(2) 0.0411(9) Uani 1 1 d . . . C5 C 0.4260(6) 0.4365(2) 0.64977(18) 0.0387(8) Uani 1 1 d . . . C6 C 0.4397(6) 0.4889(2) 0.7184(2) 0.0412(8) Uani 1 1 d . . . C7 C 0.2647(7) 0.5566(2) 0.7286(2) 0.0473(9) Uani 1 1 d . . . C8 C 0.2477(6) 0.4578(2) 0.5860(2) 0.0420(9) Uani 1 1 d . . . C9 C 0.7314(7) 0.3038(2) 0.5236(2) 0.0509(10) Uani 1 1 d . . . H9A H 0.8403 0.3491 0.5278 0.061 Uiso 1 1 calc R . . C10 C 0.7344(7) 0.2424(3) 0.4613(2) 0.0567(10) Uani 1 1 d . . . H10A H 0.8423 0.2478 0.4244 0.068 Uiso 1 1 calc R . . C11 C 0.5765(7) 0.1740(3) 0.4550(2) 0.0542(10) Uani 1 1 d . . . H11A H 0.5759 0.1334 0.4136 0.065 Uiso 1 1 calc R . . C12 C 0.4176(6) 0.1663(2) 0.5114(2) 0.0422(9) Uani 1 1 d . . . C13 C 0.4151(6) 0.2277(2) 0.57355(19) 0.0382(8) Uani 1 1 d . . . C14 C 0.5730(6) 0.2992(2) 0.57874(19) 0.0412(8) Uani 1 1 d . . . C15 C 0.2511(6) 0.2135(2) 0.6330(2) 0.0413(8) Uani 1 1 d . . . C16 C 0.2451(7) 0.0964(2) 0.5060(2) 0.0448(9) Uani 1 1 d . . . N1 N 0.0955(5) 0.52019(19) 0.59627(18) 0.0512(8) Uani 1 1 d . . . N2 N 0.1062(6) 0.5672(2) 0.66673(17) 0.0535(9) Uani 1 1 d . . . H2B H 0.0015 0.6066 0.6711 0.064 Uiso 1 1 calc R . . N3 N 0.0951(6) 0.08678(18) 0.55649(17) 0.0472(8) Uani 1 1 d . . . N4 N 0.1010(5) 0.14627(18) 0.61829(17) 0.0464(8) Uani 1 1 d . . . H4A H -0.0022 0.1399 0.6510 0.056 Uiso 1 1 calc R . . O1 O 0.2386(5) 0.41845(16) 0.51783(14) 0.0558(8) Uani 1 1 d . . . H1 H 0.1291 0.4378 0.4886 0.080 Uiso 1 1 calc R . . O2 O 0.2611(5) 0.60217(18) 0.78994(16) 0.0643(8) Uani 1 1 d . . . O3 O 0.2436(5) 0.25909(16) 0.69387(16) 0.0557(7) Uani 1 1 d . . . O4 O 0.2475(5) 0.04087(17) 0.44463(15) 0.0636(8) Uani 1 1 d . . . H4 H 0.1456 0.0037 0.4468 0.080 Uiso 1 1 calc R . . OW1 O 0.2231(9) 0.1984(3) 0.8430(2) 0.0569(16) Uani 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 C1 0.061(3) 0.053(2) 0.045(2) -0.0087(17) 0.0022(19) -0.0060(19) C2 0.053(3) 0.069(3) 0.049(2) -0.0008(19) -0.0106(19) -0.004(2) C3 0.044(2) 0.060(2) 0.056(2) -0.0018(19) 0.001(2) 0.0026(17) C4 0.041(2) 0.0395(19) 0.0431(19) -0.0002(15) 0.0042(16) -0.0043(15) C5 0.043(2) 0.0345(17) 0.0394(18) 0.0034(14) 0.0057(16) -0.0054(14) C6 0.045(2) 0.0382(18) 0.0406(19) -0.0011(14) 0.0064(16) -0.0080(14) C7 0.055(3) 0.0422(19) 0.046(2) -0.0027(17) 0.0114(18) -0.0043(17) C8 0.047(2) 0.0380(18) 0.041(2) 0.0001(15) 0.0036(17) -0.0035(16) C9 0.049(2) 0.048(2) 0.057(2) -0.0004(17) 0.0110(19) -0.0053(17) C10 0.057(3) 0.064(2) 0.052(2) -0.0012(19) 0.0203(19) -0.0058(19) C11 0.062(3) 0.053(2) 0.049(2) -0.0078(17) 0.014(2) -0.0002(19) C12 0.047(2) 0.0377(18) 0.0420(19) 0.0010(14) 0.0054(17) 0.0026(15) C13 0.040(2) 0.0325(17) 0.0414(18) 0.0026(14) 0.0020(15) 0.0024(14) C14 0.042(2) 0.0407(19) 0.0410(19) 0.0044(15) 0.0032(16) 0.0001(15) C15 0.045(2) 0.0343(18) 0.046(2) 0.0006(15) 0.0095(17) 0.0009(15) C16 0.057(3) 0.0362(18) 0.0406(19) 0.0010(15) 0.0036(18) -0.0033(16) N1 0.055(2) 0.0492(18) 0.0482(18) -0.0042(14) 0.0002(15) 0.0062(15) N2 0.063(2) 0.0520(19) 0.0464(18) -0.0038(14) 0.0086(17) 0.0117(15) N3 0.054(2) 0.0418(16) 0.0450(17) -0.0017(13) 0.0033(16) -0.0043(13) N4 0.049(2) 0.0408(16) 0.0507(17) -0.0029(13) 0.0106(15) -0.0061(13) O1 0.0603(18) 0.0552(15) 0.0486(15) -0.0063(12) -0.0113(13) 0.0110(12) O2 0.075(2) 0.0636(17) 0.0562(17) -0.0170(14) 0.0133(15) 0.0025(14) O3 0.0611(18) 0.0519(15) 0.0574(15) -0.0120(13) 0.0225(13) -0.0097(12) O4 0.081(2) 0.0559(16) 0.0552(16) -0.0144(13) 0.0139(15) -0.0220(14) OW1 0.066(4) 0.085(4) 0.017(2) 0.000(2) -0.005(2) -0.070(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.353(6) . ? C1 C6 1.397(5) . ? C2 C3 1.393(5) . ? C3 C4 1.371(5) . ? C4 C5 1.421(5) . ? C4 C14 1.500(5) . ? C5 C6 1.397(4) . ? C5 C8 1.456(4) . ? C6 C7 1.465(5) . ? C7 O2 1.244(4) . ? C7 N2 1.333(4) . ? C8 O1 1.290(4) . ? C8 N1 1.315(4) . ? C9 C14 1.374(5) . ? C9 C10 1.402(5) . ? C10 C11 1.378(6) . ? C11 C12 1.394(5) . ? C12 C13 1.400(5) . ? C12 C16 1.453(5) . ? C13 C14 1.414(5) . ? C13 C15 1.466(5) . ? C15 O3 1.240(4) . ? C15 N4 1.346(4) . ? C16 N3 1.286(5) . ? C16 O4 1.333(4) . ? N1 N2 1.380(4) . ? N3 N4 1.373(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 C2 C1 C6 119.8(3) . . ? C1 C2 C3 120.4(4) . . ? C4 C3 C2 121.7(4) . . ? C3 C4 C5 118.3(3) . . ? C3 C4 C14 117.7(3) . . ? C5 C4 C14 124.0(3) . . ? C6 C5 C4 119.0(3) . . ? C6 C5 C8 117.8(3) . . ? C4 C5 C8 123.2(3) . . ? C1 C6 C5 120.5(3) . . ? C1 C6 C7 119.0(3) . . ? C5 C6 C7 120.5(3) . . ? O2 C7 N2 121.3(3) . . ? O2 C7 C6 123.4(3) . . ? N2 C7 C6 115.3(3) . . ? O1 C8 N1 118.5(3) . . ? O1 C8 C5 121.4(3) . . ? N1 C8 C5 120.1(3) . . ? C14 C9 C10 122.2(4) . . ? C11 C10 C9 119.6(4) . . ? C10 C11 C12 119.5(3) . . ? C11 C12 C13 120.8(3) . . ? C11 C12 C16 121.2(3) . . ? C13 C12 C16 118.0(3) . . ? C12 C13 C14 119.7(3) . . ? C12 C13 C15 118.1(3) . . ? C14 C13 C15 122.1(3) . . ? C9 C14 C13 118.2(3) . . ? C9 C14 C4 119.0(3) . . ? C13 C14 C4 122.7(3) . . ? O3 C15 N4 119.7(3) . . ? O3 C15 C13 124.3(3) . . ? N4 C15 C13 116.0(3) . . ? N3 C16 O4 120.2(3) . . ? N3 C16 C12 123.4(3) . . ? O4 C16 C12 116.4(3) . . ? C8 N1 N2 120.4(3) . . ? C7 N2 N1 125.6(3) . . ? C16 N3 N4 117.4(3) . . ? C15 N4 N3 126.8(3) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.682 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 951028' ####################################################################### # # 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_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Mn N6 O8' _chemical_formula_weight 479.32 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' Mn Mn 0.3368 0.7283 '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 7.6372(4) _cell_length_b 7.7850(5) _cell_length_c 8.9475(7) _cell_angle_alpha 83.833(4) _cell_angle_beta 71.494(4) _cell_angle_gamma 67.412(4) _cell_volume 465.71(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1019 _cell_measurement_theta_min 2.8342 _cell_measurement_theta_max 25.0344 _exptl_crystal_description COLUMNAR _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 247 _exptl_absorpt_coefficient_mu 0.772 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.903 _exptl_absorpt_correction_T_max 0.926 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 2646 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1644 _reflns_number_gt 1553 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMAR' _computing_cell_refinement 'Bruker SMAR' _computing_data_reduction 'Bruker SMAR' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0642P)^2^+0.1159P] 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 1644 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 Mn1 Mn 0.5000 -0.5000 0.0000 0.02501(18) Uani 1 2 d S . . N1 N 0.5076(2) -0.6300(2) 0.24325(18) 0.0243(4) Uani 1 1 d . . . N2 N 0.0655(2) -0.2334(2) 0.41680(18) 0.0303(4) Uani 1 1 d . . . N3 N 0.0267(2) -0.2942(2) 0.57031(19) 0.0299(4) Uani 1 1 d . . . H2A H -0.0792 -0.2221 0.6366 0.036 Uiso 1 1 calc R . . OW1 O 0.2761(2) -0.6193(2) -0.0018(2) 0.0343(4) Uani 1 1 d . . . H01 H 0.193(5) -0.594(4) 0.059(4) 0.049(10) Uiso 1 1 d . . . H03 H 0.243(5) -0.594(4) -0.084(4) 0.055(9) Uiso 1 1 d . . . OW2 O 0.3193(3) 0.0439(3) 0.2005(2) 0.0457(4) Uani 1 1 d . . . H02 H 0.308(4) -0.047(5) 0.177(3) 0.056(9) Uiso 1 1 d . . . H04 H 0.334(5) 0.092(6) 0.116(4) 0.085(13) Uiso 1 1 d . . . O1 O 0.2737(2) -0.29262(19) 0.16746(15) 0.0304(3) Uani 1 1 d . . . O2 O 0.0816(2) -0.4862(2) 0.77388(16) 0.0367(4) Uani 1 1 d . . . C1 C 0.6323(3) -0.7885(3) 0.2850(2) 0.0268(4) Uani 1 1 d . . . C2 C 0.6043(3) -0.8440(3) 0.4426(2) 0.0295(4) Uani 1 1 d . . . H3A H 0.6973 -0.9515 0.4686 0.035 Uiso 1 1 calc R . . C3 C 0.4402(3) -0.7398(3) 0.5579(2) 0.0294(4) Uani 1 1 d . . . H5A H 0.4169 -0.7779 0.6621 0.035 Uiso 1 1 calc R . . C4 C 0.3081(3) -0.5742(3) 0.5153(2) 0.0241(4) Uani 1 1 d . . . C5 C 0.3490(3) -0.5234(3) 0.3590(2) 0.0220(4) Uani 1 1 d . . . C6 C 0.2231(3) -0.3431(3) 0.3124(2) 0.0250(4) Uani 1 1 d . . . C7 C 0.1325(3) -0.4509(3) 0.6295(2) 0.0272(4) Uani 1 1 d . . . C8 C 0.8074(3) -0.9063(3) 0.1583(3) 0.0425(6) Uani 1 1 d . . . H1B H 0.8048 -0.8491 0.0581 0.064 Uiso 1 1 calc R . . H1C H 0.8020 -1.0273 0.1571 0.064 Uiso 1 1 calc R . . H1D H 0.9277 -0.9181 0.1784 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0228(3) 0.0287(3) 0.0162(2) 0.00144(16) -0.00155(16) -0.00559(18) N1 0.0216(8) 0.0269(8) 0.0196(8) 0.0015(6) -0.0036(6) -0.0062(7) N2 0.0253(8) 0.0338(9) 0.0219(8) -0.0006(7) -0.0050(7) -0.0021(7) N3 0.0217(8) 0.0381(10) 0.0193(8) -0.0033(7) -0.0001(6) -0.0038(7) OW1 0.0257(8) 0.0484(9) 0.0245(8) 0.0017(7) -0.0034(7) -0.0127(7) OW2 0.0531(11) 0.0365(9) 0.0407(10) 0.0005(8) -0.0089(8) -0.0135(8) O1 0.0320(8) 0.0285(7) 0.0181(7) 0.0035(5) -0.0031(6) -0.0022(6) O2 0.0286(8) 0.0562(10) 0.0178(7) 0.0038(6) -0.0015(6) -0.0131(7) C1 0.0243(10) 0.0261(10) 0.0266(10) 0.0018(8) -0.0088(8) -0.0052(8) C2 0.0297(10) 0.0265(10) 0.0292(10) 0.0050(8) -0.0111(8) -0.0065(8) C3 0.0339(11) 0.0326(11) 0.0237(10) 0.0078(8) -0.0103(8) -0.0150(9) C4 0.0217(9) 0.0306(10) 0.0210(9) 0.0014(7) -0.0051(7) -0.0120(8) C5 0.0184(9) 0.0263(9) 0.0203(9) 0.0010(7) -0.0051(7) -0.0081(8) C6 0.0216(9) 0.0292(10) 0.0206(9) 0.0005(7) -0.0043(7) -0.0074(8) C7 0.0222(10) 0.0387(11) 0.0203(9) 0.0006(8) -0.0038(8) -0.0131(9) C8 0.0362(12) 0.0405(12) 0.0301(11) -0.0012(9) -0.0063(9) 0.0051(10) _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 Mn1 O1 2.1379(13) 2_645 ? Mn1 O1 2.1379(13) . ? Mn1 OW1 2.2425(16) . ? Mn1 OW1 2.2425(16) 2_645 ? Mn1 N1 2.3078(15) . ? Mn1 N1 2.3078(15) 2_645 ? N1 C1 1.340(3) . ? N1 C5 1.358(2) . ? N2 C6 1.311(3) . ? N2 N3 1.381(2) . ? N3 C7 1.341(3) . ? O1 C6 1.294(2) . ? O2 C7 1.258(2) . ? C1 C2 1.403(3) . ? C1 C8 1.494(3) . ? C2 C3 1.368(3) . ? C3 C4 1.401(3) . ? C4 C5 1.382(3) . ? C4 C7 1.454(3) . ? C5 C6 1.470(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 Mn1 O1 180.0 2_645 . ? O1 Mn1 OW1 90.36(6) 2_645 . ? O1 Mn1 OW1 89.64(6) . . ? O1 Mn1 OW1 89.64(6) 2_645 2_645 ? O1 Mn1 OW1 90.36(6) . 2_645 ? OW1 Mn1 OW1 180.00(9) . 2_645 ? O1 Mn1 N1 105.08(5) 2_645 . ? O1 Mn1 N1 74.92(5) . . ? OW1 Mn1 N1 89.42(6) . . ? OW1 Mn1 N1 90.58(6) 2_645 . ? O1 Mn1 N1 74.92(5) 2_645 2_645 ? O1 Mn1 N1 105.08(5) . 2_645 ? OW1 Mn1 N1 90.58(6) . 2_645 ? OW1 Mn1 N1 89.42(6) 2_645 2_645 ? N1 Mn1 N1 180.00(8) . 2_645 ? C1 N1 C5 117.78(16) . . ? C1 N1 Mn1 131.67(13) . . ? C5 N1 Mn1 110.49(11) . . ? C6 N2 N3 117.05(16) . . ? C7 N3 N2 128.49(16) . . ? C6 O1 Mn1 117.19(12) . . ? N1 C1 C2 122.00(17) . . ? N1 C1 C8 118.07(17) . . ? C2 C1 C8 119.93(17) . . ? C3 C2 C1 119.94(18) . . ? C2 C3 C4 118.45(18) . . ? C5 C4 C3 118.68(17) . . ? C5 C4 C7 118.56(17) . . ? C3 C4 C7 122.74(17) . . ? N1 C5 C4 123.05(17) . . ? N1 C5 C6 116.84(16) . . ? C4 C5 C6 120.06(17) . . ? O1 C6 N2 120.69(17) . . ? O1 C6 C5 118.76(16) . . ? N2 C6 C5 120.52(16) . . ? O2 C7 N3 121.57(18) . . ? O2 C7 C4 123.23(18) . . ? N3 C7 C4 115.20(16) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.439 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 951029' ####################################################################### # # 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_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Cl2 N8 O4' _chemical_formula_weight 453.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/C 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 13.175(3) _cell_length_b 18.284(4) _cell_length_c 7.2832(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.66(3) _cell_angle_gamma 90.00 _cell_volume 1754.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10531 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.465 _exptl_crystal_description COLUMNAR _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.716 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.419 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.947 _exptl_absorpt_correction_T_max 0.955 _exptl_absorpt_process_details Process-auto _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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16626 _diffrn_reflns_av_R_equivalents 0.0658 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3944 _reflns_number_gt 2539 _reflns_threshold_expression >2sigma(I) _computing_data_collection Process-auto _computing_cell_refinement Process-auto _computing_data_reduction Process-auto _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0683P)^2^+0.2086P] 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 3944 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1396 _refine_ls_wR_factor_gt 0.1264 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 N1 N 0.88257(16) -0.34241(11) 0.1191(3) 0.0276(5) Uani 1 1 d . . . H1A H 0.8387 -0.3745 0.0840 0.033 Uiso 1 1 calc R . . N2 N 0.97272(16) -0.36924(11) 0.1905(3) 0.0269(5) Uani 1 1 d . . . N3 N 0.62254(16) -0.15274(12) 0.3858(3) 0.0297(5) Uani 1 1 d . . . H3A H 0.6661 -0.1840 0.4266 0.036 Uiso 1 1 calc R . . N4 N 0.52837(16) -0.18003(12) 0.3349(3) 0.0313(5) Uani 1 1 d . . . N5 N 0.96095(17) -0.01912(12) 0.2042(4) 0.0396(6) Uani 1 1 d . . . H5A H 1.0081 0.0109 0.2367 0.048 Uiso 1 1 calc R . . N6 N 0.86825(19) 0.00836(13) 0.1437(4) 0.0355(6) Uani 1 1 d . . . N7 N 0.55525(18) 0.16762(12) 0.2212(4) 0.0387(6) Uani 1 1 d . . . H7A H 0.5121 0.1962 0.1681 0.046 Uiso 1 1 calc R . . N8 N 0.6449(2) 0.19659(14) 0.2887(6) 0.0473(8) Uani 1 1 d . . . O1 O 0.77299(14) -0.25448(10) 0.0270(3) 0.0386(5) Uani 1 1 d . . . O2 O 1.12867(13) -0.34451(10) 0.3128(3) 0.0357(5) Uani 1 1 d . . . H2 H 1.1300 -0.3893 0.3127 0.080 Uiso 1 1 calc . . . O3 O 0.74205(13) -0.06524(9) 0.4273(3) 0.0342(5) Uani 1 1 d . . . O4 O 0.36939(14) -0.15492(10) 0.2262(3) 0.0464(6) Uani 1 1 d . . . H4 H 0.3652 -0.1993 0.2412 0.080 Uiso 1 1 calc . . . Cl1 Cl 1.15815(5) -0.05530(4) 0.37197(11) 0.0381(2) Uani 1 1 d . . . Cl2 Cl 0.34598(5) 0.13036(4) 0.10723(10) 0.0378(2) Uani 1 1 d . . . C1 C 0.97931(19) -0.09317(13) 0.2133(4) 0.0260(6) Uani 1 1 d . . . C2 C 0.90953(19) -0.14453(13) 0.1496(4) 0.0265(6) Uani 1 1 d . . . H2C H 0.8482 -0.1291 0.0984 0.032 Uiso 1 1 calc R . . C3 C 0.93093(19) -0.21894(13) 0.1618(4) 0.0237(6) Uani 1 1 d . . . C4 C 1.02318(18) -0.24356(13) 0.2345(3) 0.0227(5) Uani 1 1 d . . . C5 C 1.09543(19) -0.19223(13) 0.2966(4) 0.0259(6) Uani 1 1 d . . . H5B H 1.1578 -0.2075 0.3438 0.031 Uiso 1 1 calc R . . C6 C 1.07222(19) -0.11916(14) 0.2860(4) 0.0266(6) Uani 1 1 d . . . C7 C 0.85538(19) -0.27197(13) 0.0981(4) 0.0265(6) Uani 1 1 d . . . C8 C 1.03905(19) -0.32137(14) 0.2446(4) 0.0254(6) Uani 1 1 d . . . C9 C 0.5327(2) 0.09382(13) 0.2365(4) 0.0265(6) Uani 1 1 d . . . C10 C 0.60366(19) 0.04329(13) 0.2997(4) 0.0281(6) Uani 1 1 d . . . H10A H 0.6682 0.0589 0.3348 0.034 Uiso 1 1 calc R . . C11 C 0.57901(19) -0.03020(13) 0.3108(4) 0.0242(6) Uani 1 1 d . . . C12 C 0.48250(18) -0.05525(14) 0.2575(4) 0.0253(6) Uani 1 1 d . . . C13 C 0.41040(19) -0.00462(14) 0.1946(4) 0.0271(6) Uani 1 1 d . . . H13A H 0.3458 -0.0202 0.1597 0.033 Uiso 1 1 calc R . . C14 C 0.43548(19) 0.06797(14) 0.1846(4) 0.0266(6) Uani 1 1 d . . . C15 C 0.65331(19) -0.08276(13) 0.3782(4) 0.0257(6) Uani 1 1 d . . . C16 C 0.46265(19) -0.13224(14) 0.2745(4) 0.0292(6) Uani 1 1 d . . . H01 H 0.859(2) -0.0029(17) 0.031(4) 0.043(10) Uiso 1 1 d . . . H03 H 0.657(3) 0.177(2) 0.411(6) 0.087(15) Uiso 1 1 d . . . H02 H 0.685(3) 0.1815(19) 0.212(5) 0.045(11) Uiso 1 1 d . . . H00 H 0.817(3) -0.014(2) 0.221(5) 0.064(11) 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 0.0259(11) 0.0147(11) 0.0421(14) -0.0027(9) -0.0091(10) -0.0022(9) N2 0.0265(11) 0.0171(11) 0.0369(13) -0.0005(9) -0.0041(10) 0.0019(9) N3 0.0243(11) 0.0184(11) 0.0463(15) 0.0062(10) -0.0089(11) 0.0005(9) N4 0.0248(11) 0.0184(11) 0.0507(15) 0.0029(10) -0.0029(11) -0.0011(9) N5 0.0337(13) 0.0150(12) 0.0698(18) -0.0064(11) -0.0120(13) -0.0045(9) N6 0.0356(14) 0.0222(13) 0.0487(17) 0.0003(11) -0.0067(14) -0.0004(10) N7 0.0374(13) 0.0149(11) 0.0635(17) 0.0077(11) -0.0127(13) 0.0063(9) N8 0.0351(15) 0.0217(13) 0.085(3) 0.0044(14) -0.0051(17) 0.0015(11) O1 0.0337(10) 0.0211(10) 0.0604(14) -0.0026(9) -0.0231(10) 0.0015(8) O2 0.0308(10) 0.0166(9) 0.0592(14) 0.0012(8) -0.0126(10) 0.0018(7) O3 0.0275(10) 0.0195(9) 0.0552(13) 0.0051(8) -0.0134(9) -0.0004(7) O4 0.0274(10) 0.0189(10) 0.0928(18) -0.0015(10) -0.0118(11) -0.0021(8) Cl1 0.0319(4) 0.0232(4) 0.0589(5) -0.0068(3) -0.0094(3) -0.0073(3) Cl2 0.0337(4) 0.0267(4) 0.0527(5) 0.0042(3) -0.0102(3) 0.0107(3) C1 0.0299(13) 0.0155(12) 0.0326(15) -0.0019(10) -0.0028(12) -0.0028(10) C2 0.0260(13) 0.0173(13) 0.0359(15) -0.0016(10) -0.0068(12) 0.0007(10) C3 0.0264(13) 0.0174(12) 0.0272(14) -0.0009(10) -0.0010(11) -0.0032(10) C4 0.0262(13) 0.0169(12) 0.0250(13) -0.0013(10) -0.0022(11) 0.0004(10) C5 0.0248(12) 0.0193(13) 0.0336(15) -0.0013(11) -0.0014(12) 0.0000(10) C6 0.0276(13) 0.0174(13) 0.0348(15) -0.0056(10) -0.0017(12) -0.0047(10) C7 0.0292(14) 0.0183(13) 0.0318(15) -0.0022(10) -0.0042(12) -0.0032(10) C8 0.0270(13) 0.0165(12) 0.0327(15) 0.0007(10) -0.0010(12) 0.0019(10) C9 0.0296(14) 0.0181(13) 0.0320(15) 0.0008(10) -0.0012(12) 0.0018(10) C10 0.0250(12) 0.0195(13) 0.0395(16) 0.0000(11) -0.0070(12) 0.0021(10) C11 0.0284(13) 0.0149(12) 0.0292(14) 0.0006(10) -0.0027(12) 0.0028(10) C12 0.0233(12) 0.0189(13) 0.0335(15) 0.0010(10) -0.0016(11) 0.0022(10) C13 0.0239(12) 0.0236(14) 0.0338(15) -0.0006(11) -0.0037(12) 0.0032(10) C14 0.0270(13) 0.0233(14) 0.0294(15) 0.0012(11) -0.0035(12) 0.0092(10) C15 0.0277(13) 0.0163(12) 0.0330(15) 0.0019(10) -0.0050(12) 0.0014(10) C16 0.0261(13) 0.0182(13) 0.0431(17) -0.0012(11) -0.0024(13) -0.0010(10) _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 C7 1.345(3) . ? N1 N2 1.381(3) . ? N2 C8 1.295(3) . ? N3 C15 1.344(3) . ? N3 N4 1.384(3) . ? N4 C16 1.303(3) . ? N5 C1 1.377(3) . ? N5 N6 1.388(3) . ? N7 N8 1.380(3) . ? N7 C9 1.386(3) . ? O1 C7 1.239(3) . ? O2 C8 1.344(3) . ? O3 C15 1.260(3) . ? O4 C16 1.340(3) . ? Cl1 C6 1.738(2) . ? Cl2 C14 1.730(2) . ? C1 C2 1.390(3) . ? C1 C6 1.410(3) . ? C2 C3 1.392(3) . ? C3 C4 1.395(3) . ? C3 C7 1.461(3) . ? C4 C5 1.407(3) . ? C4 C8 1.440(3) . ? C5 C6 1.372(3) . ? C9 C10 1.389(3) . ? C9 C14 1.413(3) . ? C10 C11 1.385(3) . ? C11 C12 1.402(3) . ? C11 C15 1.453(3) . ? C12 C13 1.400(3) . ? C12 C16 1.437(4) . ? C13 C14 1.370(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 C7 N1 N2 127.6(2) . . ? C8 N2 N1 116.7(2) . . ? C15 N3 N4 127.0(2) . . ? C16 N4 N3 116.0(2) . . ? C1 N5 N6 121.7(2) . . ? N8 N7 C9 121.9(2) . . ? N5 C1 C2 122.2(2) . . ? N5 C1 C6 120.1(2) . . ? C2 C1 C6 117.7(2) . . ? C1 C2 C3 120.4(2) . . ? C2 C3 C4 121.0(2) . . ? C2 C3 C7 119.4(2) . . ? C4 C3 C7 119.6(2) . . ? C3 C4 C5 119.3(2) . . ? C3 C4 C8 117.6(2) . . ? C5 C4 C8 123.0(2) . . ? C6 C5 C4 118.8(2) . . ? C5 C6 C1 122.7(2) . . ? C5 C6 Cl1 119.3(2) . . ? C1 C6 Cl1 117.88(19) . . ? O1 C7 N1 121.7(2) . . ? O1 C7 C3 123.5(2) . . ? N1 C7 C3 114.8(2) . . ? N2 C8 O2 119.1(2) . . ? N2 C8 C4 123.7(2) . . ? O2 C8 C4 117.1(2) . . ? N7 C9 C10 122.0(2) . . ? N7 C9 C14 119.9(2) . . ? C10 C9 C14 118.1(2) . . ? C11 C10 C9 120.5(2) . . ? C10 C11 C12 120.9(2) . . ? C10 C11 C15 120.3(2) . . ? C12 C11 C15 118.9(2) . . ? C13 C12 C11 119.0(2) . . ? C13 C12 C16 123.5(2) . . ? C11 C12 C16 117.5(2) . . ? C14 C13 C12 119.7(2) . . ? C13 C14 C9 121.9(2) . . ? C13 C14 Cl2 119.48(19) . . ? C9 C14 Cl2 118.6(2) . . ? O3 C15 N3 120.7(2) . . ? O3 C15 C11 123.2(2) . . ? N3 C15 C11 116.2(2) . . ? N4 C16 O4 119.0(2) . . ? N4 C16 C12 124.4(2) . . ? O4 C16 C12 116.6(2) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.650 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 951030'