# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Herbert, Matthew' 'Alvarez, Eleuterio' 'Cole-Hamilton, David' 'Montilla, Francisco' 'Galindo, Agustin' _publ_contact_author_name 'Galindo, Agustin' _publ_contact_author_email galindo@us.es _publ_section_title ; Olefin epoxidation by hydrogen peroxide catalysed by molybdenum complexes in ionic liquids and structural characterisation of the proposed intermediate dioxoperoxomolybdenum species ; # Attachment '- Complex_1.cif' data_ea08709a _database_code_depnum_ccdc_archive 'CCDC 770508' #TrackingRef '- Complex_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H48 Mo4 N12 O16, 2(C H2 Cl2)' _chemical_formula_sum 'C32 H52 Cl4 Mo4 N12 O16' _chemical_formula_weight 1386.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mo Mo -1.6832 0.6857 '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 _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.0998(9) _cell_length_b 10.0755(6) _cell_length_c 18.6382(12) _cell_angle_alpha 90.00 _cell_angle_beta 103.831(2) _cell_angle_gamma 90.00 _cell_volume 2571.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9964 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 30.51 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.791 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 1.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5927 _exptl_absorpt_correction_T_max 0.6904 _exptl_absorpt_process_details ; SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical X-ray Solutions, Madison, Wisconsin, USA. ; _diffrn_ambient_temperature 173(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-Nonius X8kappa APEX II CCD area detector' ; _diffrn_measurement_method 'phi and omega scans with narrow frames' _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_decay_% 0 _diffrn_reflns_number 57206 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 30.65 _reflns_number_total 7927 _reflns_number_gt 7021 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker (2006). APEX 2. Version 2.1.' _computing_cell_refinement 'Bruker (2006). APEX 2. Version 2.1.' _computing_data_reduction 'Bruker (2006). APEX 2. Version 2.1.' _computing_structure_solution 'Bruker (2006). APEX 2. Version 2.1.' _computing_structure_refinement 'XL, SHELXTL v. 6.14 (Bruker, 2003)' _computing_molecular_graphics 'XP, SHELXTL v. 6.14 (Bruker, 2003)' _computing_publication_material 'XCIF, SHELXTL v. 6.14 (Bruker, 2003)' _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^)+(0.0283P)^2^+4.0629P] 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 7927 _refine_ls_number_parameters 322 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0708 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mo1 Mo 0.029458(13) 0.577301(17) 0.072710(9) 0.01568(5) Uani 1 1 d . . . Mo2 Mo 0.281218(13) 0.363572(18) 0.088422(10) 0.01818(5) Uani 1 1 d . . . O1 O -0.01900(11) 0.40506(15) 0.03361(8) 0.0175(3) Uani 1 1 d . . . O2 O 0.12183(12) 0.68215(16) 0.14596(8) 0.0227(3) Uani 1 1 d . . . O3 O 0.11437(12) 0.73028(16) 0.07166(8) 0.0218(3) Uani 1 1 d . . . O4 O -0.07517(12) 0.65037(17) 0.07868(9) 0.0234(3) Uani 1 1 d . . . O5 O 0.17555(11) 0.46248(15) 0.07750(8) 0.0200(3) Uani 1 1 d . . . O6 O 0.28771(14) 0.21577(17) 0.02441(10) 0.0299(4) Uani 1 1 d . . . O7 O 0.33921(14) 0.33113(18) 0.00645(10) 0.0311(4) Uani 1 1 d . . . O8 O 0.35879(13) 0.35472(18) 0.17400(10) 0.0291(4) Uani 1 1 d . . . N1 N 0.04330(13) 0.46695(19) 0.17642(10) 0.0205(3) Uani 1 1 d . . . N2 N 0.13207(14) 0.4500(2) 0.22356(10) 0.0223(4) Uani 1 1 d D . . H2N H 0.1816(17) 0.499(3) 0.2190(16) 0.027 Uiso 1 1 d D . . N3 N 0.19347(14) 0.20788(19) 0.12526(10) 0.0215(4) Uani 1 1 d . . . N4 N 0.09648(14) 0.19854(19) 0.09367(11) 0.0222(4) Uani 1 1 d D . . H4N H 0.0639(19) 0.267(2) 0.0714(15) 0.027 Uiso 1 1 d D . . N5 N 0.35370(14) 0.5529(2) 0.07483(11) 0.0229(4) Uani 1 1 d . . . N6 N 0.30045(14) 0.6630(2) 0.05182(11) 0.0244(4) Uani 1 1 d D . . H6N H 0.2389(13) 0.670(3) 0.0517(16) 0.029 Uiso 1 1 d D . . C1 C 0.52887(18) 0.4897(3) 0.10356(16) 0.0331(5) Uani 1 1 d . . . H1A H 0.5328 0.4604 0.1543 0.050 Uiso 1 1 calc R . . H1B H 0.5905 0.5320 0.1009 0.050 Uiso 1 1 calc R . . H1C H 0.5169 0.4128 0.0704 0.050 Uiso 1 1 calc R . . C15 C 0.12968(19) 0.3578(3) 0.27460(12) 0.0268(5) Uani 1 1 d . . . C16 C 0.21806(18) 0.0928(2) 0.16150(13) 0.0249(4) Uani 1 1 d . . . C18 C 0.13604(18) 0.0130(2) 0.15325(13) 0.0258(5) Uani 1 1 d . . . H18 H 0.1331 -0.0730 0.1735 0.031 Uiso 1 1 calc R . . C19 C 0.05942(18) 0.0832(2) 0.10979(13) 0.0244(4) Uani 1 1 d . . . C20 C 0.44725(17) 0.5867(2) 0.08085(13) 0.0257(5) Uani 1 1 d . . . C21 C -0.01746(18) 0.3843(3) 0.19967(13) 0.0252(5) Uani 1 1 d . . . C22 C 0.0343(2) 0.3141(3) 0.26087(13) 0.0307(5) Uani 1 1 d . . . H22 H 0.0089 0.2488 0.2879 0.037 Uiso 1 1 calc R . . C23 C 0.3201(2) 0.0620(3) 0.20205(18) 0.0400(7) Uani 1 1 d . . . H23A H 0.3623 0.0604 0.1672 0.060 Uiso 1 1 calc R . . H23B H 0.3218 -0.0249 0.2259 0.060 Uiso 1 1 calc R . . H23C H 0.3433 0.1302 0.2397 0.060 Uiso 1 1 calc R . . C24 C 0.3133(2) 0.8975(3) 0.01866(18) 0.0373(6) Uani 1 1 d . . . H24A H 0.2867 0.8955 -0.0350 0.056 Uiso 1 1 calc R . . H24B H 0.3636 0.9664 0.0310 0.056 Uiso 1 1 calc R . . H24C H 0.2607 0.9173 0.0432 0.056 Uiso 1 1 calc R . . C25 C 0.45195(18) 0.7204(3) 0.06197(15) 0.0312(5) Uani 1 1 d . . . H25 H 0.5091 0.7700 0.0615 0.037 Uiso 1 1 calc R . . C26 C 0.35686(18) 0.7661(2) 0.04408(14) 0.0270(5) Uani 1 1 d . . . C27 C -0.1238(2) 0.3775(3) 0.16299(15) 0.0373(6) Uani 1 1 d . . . H27A H -0.1540 0.4642 0.1664 0.056 Uiso 1 1 calc R . . H27B H -0.1552 0.3104 0.1876 0.056 Uiso 1 1 calc R . . H27C H -0.1321 0.3534 0.1109 0.056 Uiso 1 1 calc R . . C28 C 0.2192(2) 0.3209(3) 0.33183(15) 0.0396(7) Uani 1 1 d . . . H28A H 0.2765 0.3291 0.3111 0.059 Uiso 1 1 calc R . . H28B H 0.2134 0.2291 0.3476 0.059 Uiso 1 1 calc R . . H28C H 0.2264 0.3804 0.3744 0.059 Uiso 1 1 calc R . . C29 C -0.0459(2) 0.0503(3) 0.08267(18) 0.0400(7) Uani 1 1 d . . . H29A H -0.0808 0.0742 0.1204 0.060 Uiso 1 1 calc R . . H29B H -0.0532 -0.0451 0.0725 0.060 Uiso 1 1 calc R . . H29C H -0.0732 0.1001 0.0373 0.060 Uiso 1 1 calc R . . Cl1 Cl 0.31970(6) 0.68745(9) 0.24427(6) 0.0537(2) Uani 1 1 d . . . Cl2 Cl 0.45203(9) 0.59242(15) 0.37801(6) 0.0808(4) Uani 1 1 d . . . C30 C 0.4368(2) 0.6286(4) 0.28422(19) 0.0471(8) Uani 1 1 d . . . H30A H 0.4854 0.6962 0.2785 0.056 Uiso 1 1 calc R . . H30B H 0.4491 0.5474 0.2579 0.056 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 Mo1 0.01875(8) 0.01459(8) 0.01413(8) -0.00012(6) 0.00477(6) 0.00100(6) Mo2 0.01948(8) 0.01623(9) 0.01923(9) 0.00109(6) 0.00541(6) 0.00118(6) O1 0.0213(7) 0.0166(7) 0.0149(6) 0.0015(5) 0.0053(5) -0.0003(5) O2 0.0283(8) 0.0210(8) 0.0178(7) -0.0015(6) 0.0035(6) -0.0023(6) O3 0.0284(8) 0.0177(7) 0.0192(7) 0.0017(6) 0.0055(6) -0.0018(6) O4 0.0229(7) 0.0255(8) 0.0230(7) -0.0028(6) 0.0078(6) 0.0046(6) O5 0.0205(7) 0.0162(7) 0.0239(7) 0.0023(6) 0.0065(6) 0.0001(6) O6 0.0390(10) 0.0204(8) 0.0344(9) -0.0027(7) 0.0170(8) -0.0003(7) O7 0.0370(9) 0.0269(9) 0.0353(9) -0.0026(7) 0.0204(8) -0.0014(7) O8 0.0277(8) 0.0281(9) 0.0280(8) 0.0068(7) -0.0005(7) -0.0011(7) N1 0.0227(8) 0.0229(9) 0.0159(8) 0.0008(7) 0.0049(7) -0.0013(7) N2 0.0252(9) 0.0254(10) 0.0163(8) 0.0031(7) 0.0047(7) -0.0009(7) N3 0.0234(8) 0.0177(8) 0.0230(9) 0.0041(7) 0.0049(7) 0.0010(7) N4 0.0236(9) 0.0174(9) 0.0251(9) 0.0051(7) 0.0048(7) -0.0004(7) N5 0.0226(9) 0.0211(9) 0.0259(9) 0.0016(7) 0.0080(7) -0.0002(7) N6 0.0233(9) 0.0209(9) 0.0300(10) 0.0035(8) 0.0084(8) -0.0008(7) C1 0.0239(11) 0.0349(14) 0.0406(14) 0.0011(11) 0.0075(10) 0.0017(10) C15 0.0346(12) 0.0299(12) 0.0174(10) 0.0050(9) 0.0093(9) 0.0033(10) C16 0.0304(11) 0.0174(10) 0.0266(11) 0.0057(8) 0.0064(9) 0.0032(9) C18 0.0353(12) 0.0163(10) 0.0265(11) 0.0047(8) 0.0085(9) 0.0009(9) C19 0.0298(11) 0.0180(10) 0.0259(11) 0.0045(8) 0.0075(9) -0.0027(8) C20 0.0240(10) 0.0268(12) 0.0272(11) -0.0022(9) 0.0079(9) -0.0036(9) C21 0.0297(11) 0.0291(12) 0.0189(10) 0.0017(9) 0.0096(8) -0.0041(9) C22 0.0393(13) 0.0322(13) 0.0225(11) 0.0082(10) 0.0112(10) -0.0042(11) C23 0.0346(14) 0.0281(13) 0.0517(17) 0.0148(12) -0.0009(12) 0.0049(11) C24 0.0392(14) 0.0222(12) 0.0533(17) 0.0055(12) 0.0164(13) -0.0024(11) C25 0.0271(11) 0.0282(12) 0.0400(14) -0.0011(11) 0.0113(10) -0.0078(10) C26 0.0304(11) 0.0212(11) 0.0312(12) -0.0002(9) 0.0107(9) -0.0063(9) C27 0.0299(12) 0.0551(18) 0.0281(12) 0.0035(12) 0.0092(10) -0.0118(12) C28 0.0378(14) 0.0506(18) 0.0285(13) 0.0144(12) 0.0039(11) 0.0073(13) C29 0.0329(13) 0.0342(14) 0.0492(17) 0.0133(13) 0.0027(12) -0.0101(11) Cl1 0.0348(4) 0.0478(5) 0.0724(6) 0.0044(4) 0.0010(4) 0.0035(3) Cl2 0.0633(6) 0.1220(11) 0.0534(6) 0.0176(6) 0.0065(5) 0.0112(7) C30 0.0302(14) 0.060(2) 0.0491(18) -0.0064(15) 0.0060(13) 0.0034(14) _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 Mo1 O4 1.6760(16) . ? Mo1 O1 1.9420(15) . ? Mo1 O3 1.9547(16) . ? Mo1 O2 1.9560(16) . ? Mo1 O1 1.9597(14) 3_565 ? Mo1 N1 2.1979(18) . ? Mo1 O5 2.3455(15) . ? Mo1 Mo1 3.0637(4) 3_565 ? Mo2 O8 1.7072(17) . ? Mo2 O5 1.7633(15) . ? Mo2 O6 1.9240(17) . ? Mo2 O7 1.9255(17) . ? Mo2 N3 2.2066(19) . ? Mo2 N5 2.207(2) . ? O1 Mo1 1.9597(14) 3_565 ? O2 O3 1.447(2) . ? O6 O7 1.451(2) . ? N1 C21 1.339(3) . ? N1 N2 1.357(3) . ? N2 C15 1.336(3) . ? N2 H2N 0.876(17) . ? N3 C16 1.345(3) . ? N3 N4 1.357(3) . ? N4 C19 1.337(3) . ? N4 H4N 0.878(17) . ? N5 C20 1.341(3) . ? N5 N6 1.350(3) . ? N6 C26 1.337(3) . ? N6 H6N 0.869(17) . ? C1 C20 1.492(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C15 C22 1.380(4) . ? C15 C28 1.491(3) . ? C16 C18 1.386(3) . ? C16 C23 1.489(4) . ? C18 C19 1.380(3) . ? C18 H18 0.9500 . ? C19 C29 1.488(4) . ? C20 C25 1.398(4) . ? C21 C22 1.391(3) . ? C21 C27 1.494(4) . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C26 1.489(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.381(4) . ? C25 H25 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? Cl1 C30 1.745(3) . ? Cl2 C30 1.748(4) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? 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 Mo1 O1 100.43(7) . . ? O4 Mo1 O3 101.84(8) . . ? O1 Mo1 O3 149.57(6) . . ? O4 Mo1 O2 99.57(7) . . ? O1 Mo1 O2 149.36(7) . . ? O3 Mo1 O2 43.44(6) . . ? O4 Mo1 O1 99.94(7) . 3_565 ? O1 Mo1 O1 76.52(7) . 3_565 ? O3 Mo1 O1 79.43(6) . 3_565 ? O2 Mo1 O1 122.23(6) . 3_565 ? O4 Mo1 N1 93.34(8) . . ? O1 Mo1 N1 80.05(7) . . ? O3 Mo1 N1 118.81(7) . . ? O2 Mo1 N1 75.82(7) . . ? O1 Mo1 N1 154.77(7) 3_565 . ? O4 Mo1 O5 173.24(7) . . ? O1 Mo1 O5 78.49(6) . . ? O3 Mo1 O5 81.66(6) . . ? O2 Mo1 O5 78.91(6) . . ? O1 Mo1 O5 86.35(6) 3_565 . ? N1 Mo1 O5 79.89(6) . . ? O4 Mo1 Mo1 103.02(6) . 3_565 ? O1 Mo1 Mo1 38.47(4) . 3_565 ? O3 Mo1 Mo1 115.42(5) . 3_565 ? O2 Mo1 Mo1 152.44(5) . 3_565 ? O1 Mo1 Mo1 38.06(4) 3_565 3_565 ? N1 Mo1 Mo1 117.98(5) . 3_565 ? O5 Mo1 Mo1 80.38(4) . 3_565 ? O8 Mo2 O5 118.19(8) . . ? O8 Mo2 O6 115.10(8) . . ? O5 Mo2 O6 122.00(8) . . ? O8 Mo2 O7 115.71(9) . . ? O5 Mo2 O7 120.78(8) . . ? O6 Mo2 O7 44.30(7) . . ? O8 Mo2 N3 87.35(8) . . ? O5 Mo2 N3 85.21(7) . . ? O6 Mo2 N3 75.88(7) . . ? O7 Mo2 N3 120.15(8) . . ? O8 Mo2 N5 86.65(8) . . ? O5 Mo2 N5 84.25(7) . . ? O6 Mo2 N5 120.39(7) . . ? O7 Mo2 N5 76.08(8) . . ? N3 Mo2 N5 163.66(7) . . ? Mo1 O1 Mo1 103.48(7) . 3_565 ? O3 O2 Mo1 68.23(9) . . ? O2 O3 Mo1 68.33(9) . . ? Mo2 O5 Mo1 173.34(9) . . ? O7 O6 Mo2 67.90(10) . . ? O6 O7 Mo2 67.80(10) . . ? C21 N1 N2 105.95(18) . . ? C21 N1 Mo1 132.08(15) . . ? N2 N1 Mo1 120.47(14) . . ? C15 N2 N1 111.8(2) . . ? C15 N2 H2N 128.1(19) . . ? N1 N2 H2N 120.0(19) . . ? C16 N3 N4 105.68(18) . . ? C16 N3 Mo2 132.28(16) . . ? N4 N3 Mo2 119.76(14) . . ? C19 N4 N3 111.73(19) . . ? C19 N4 H4N 127.1(19) . . ? N3 N4 H4N 120.6(19) . . ? C20 N5 N6 106.25(19) . . ? C20 N5 Mo2 133.06(17) . . ? N6 N5 Mo2 120.57(14) . . ? C26 N6 N5 111.9(2) . . ? C26 N6 H6N 124(2) . . ? N5 N6 H6N 123(2) . . ? C20 C1 H1A 109.5 . . ? C20 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C20 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 C15 C22 106.2(2) . . ? N2 C15 C28 121.4(2) . . ? C22 C15 C28 132.3(2) . . ? N3 C16 C18 109.6(2) . . ? N3 C16 C23 122.5(2) . . ? C18 C16 C23 127.9(2) . . ? C19 C18 C16 106.4(2) . . ? C19 C18 H18 126.8 . . ? C16 C18 H18 126.8 . . ? N4 C19 C18 106.5(2) . . ? N4 C19 C29 122.0(2) . . ? C18 C19 C29 131.5(2) . . ? N5 C20 C25 109.2(2) . . ? N5 C20 C1 122.3(2) . . ? C25 C20 C1 128.5(2) . . ? N1 C21 C22 109.3(2) . . ? N1 C21 C27 122.0(2) . . ? C22 C21 C27 128.6(2) . . ? C15 C22 C21 106.6(2) . . ? C15 C22 H22 126.7 . . ? C21 C22 H22 126.7 . . ? C16 C23 H23A 109.5 . . ? C16 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C16 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C26 C24 H24A 109.5 . . ? C26 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C26 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C20 106.3(2) . . ? C26 C25 H25 126.9 . . ? C20 C25 H25 126.9 . . ? N6 C26 C25 106.4(2) . . ? N6 C26 C24 121.0(2) . . ? C25 C26 C24 132.6(2) . . ? C21 C27 H27A 109.5 . . ? C21 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C21 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C15 C28 H28A 109.5 . . ? C15 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C15 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C19 C29 H29A 109.5 . . ? C19 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C19 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? Cl1 C30 Cl2 112.01(19) . . ? Cl1 C30 H30A 109.2 . . ? Cl2 C30 H30A 109.2 . . ? Cl1 C30 H30B 109.2 . . ? Cl2 C30 H30B 109.2 . . ? H30A C30 H30B 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Mo1 O1 Mo1 97.84(8) . . . 3_565 ? O3 Mo1 O1 Mo1 -38.68(15) . . . 3_565 ? O2 Mo1 O1 Mo1 -132.19(11) . . . 3_565 ? O1 Mo1 O1 Mo1 0.0 3_565 . . 3_565 ? N1 Mo1 O1 Mo1 -170.56(8) . . . 3_565 ? O5 Mo1 O1 Mo1 -88.96(7) . . . 3_565 ? O4 Mo1 O2 O3 -97.16(10) . . . . ? O1 Mo1 O2 O3 132.68(13) . . . . ? O1 Mo1 O2 O3 11.09(12) 3_565 . . . ? N1 Mo1 O2 O3 171.78(11) . . . . ? O5 Mo1 O2 O3 89.54(9) . . . . ? Mo1 Mo1 O2 O3 47.60(15) 3_565 . . . ? O4 Mo1 O3 O2 91.47(10) . . . . ? O1 Mo1 O3 O2 -132.28(13) . . . . ? O1 Mo1 O3 O2 -170.47(10) 3_565 . . . ? N1 Mo1 O3 O2 -9.10(12) . . . . ? O5 Mo1 O3 O2 -82.65(9) . . . . ? Mo1 Mo1 O3 O2 -157.78(8) 3_565 . . . ? O8 Mo2 O6 O7 -101.88(12) . . . . ? O5 Mo2 O6 O7 102.92(12) . . . . ? N3 Mo2 O6 O7 177.93(12) . . . . ? N5 Mo2 O6 O7 -0.35(14) . . . . ? O8 Mo2 O7 O6 100.41(12) . . . . ? O5 Mo2 O7 O6 -105.83(12) . . . . ? N3 Mo2 O7 O6 -2.32(14) . . . . ? N5 Mo2 O7 O6 179.69(12) . . . . ? O4 Mo1 N1 C21 54.6(2) . . . . ? O1 Mo1 N1 C21 -45.4(2) . . . . ? O3 Mo1 N1 C21 160.1(2) . . . . ? O2 Mo1 N1 C21 153.7(2) . . . . ? O1 Mo1 N1 C21 -67.4(3) 3_565 . . . ? O5 Mo1 N1 C21 -125.3(2) . . . . ? Mo1 Mo1 N1 C21 -52.0(2) 3_565 . . . ? O4 Mo1 N1 N2 -141.44(17) . . . . ? O1 Mo1 N1 N2 118.54(17) . . . . ? O3 Mo1 N1 N2 -35.97(19) . . . . ? O2 Mo1 N1 N2 -42.41(16) . . . . ? O1 Mo1 N1 N2 96.6(2) 3_565 . . . ? O5 Mo1 N1 N2 38.59(16) . . . . ? Mo1 Mo1 N1 N2 111.91(15) 3_565 . . . ? C21 N1 N2 C15 1.3(3) . . . . ? Mo1 N1 N2 C15 -166.36(16) . . . . ? O8 Mo2 N3 C16 -45.9(2) . . . . ? O5 Mo2 N3 C16 -164.5(2) . . . . ? O6 Mo2 N3 C16 70.8(2) . . . . ? O7 Mo2 N3 C16 72.4(2) . . . . ? N5 Mo2 N3 C16 -114.5(3) . . . . ? O8 Mo2 N3 N4 153.92(17) . . . . ? O5 Mo2 N3 N4 35.34(17) . . . . ? O6 Mo2 N3 N4 -89.37(17) . . . . ? O7 Mo2 N3 N4 -87.70(18) . . . . ? N5 Mo2 N3 N4 85.3(3) . . . . ? C16 N3 N4 C19 1.0(3) . . . . ? Mo2 N3 N4 C19 165.87(16) . . . . ? O8 Mo2 N5 C20 54.6(2) . . . . ? O5 Mo2 N5 C20 173.3(2) . . . . ? O6 Mo2 N5 C20 -62.7(2) . . . . ? O7 Mo2 N5 C20 -63.0(2) . . . . ? N3 Mo2 N5 C20 123.2(3) . . . . ? O8 Mo2 N5 N6 -130.03(18) . . . . ? O5 Mo2 N5 N6 -11.25(17) . . . . ? O6 Mo2 N5 N6 112.70(17) . . . . ? O7 Mo2 N5 N6 112.45(18) . . . . ? N3 Mo2 N5 N6 -61.4(3) . . . . ? C20 N5 N6 C26 -1.0(3) . . . . ? Mo2 N5 N6 C26 -177.48(16) . . . . ? N1 N2 C15 C22 -1.1(3) . . . . ? N1 N2 C15 C28 179.2(2) . . . . ? N4 N3 C16 C18 -0.8(3) . . . . ? Mo2 N3 C16 C18 -163.02(17) . . . . ? N4 N3 C16 C23 178.1(2) . . . . ? Mo2 N3 C16 C23 16.0(4) . . . . ? N3 C16 C18 C19 0.4(3) . . . . ? C23 C16 C18 C19 -178.5(3) . . . . ? N3 N4 C19 C18 -0.7(3) . . . . ? N3 N4 C19 C29 178.9(2) . . . . ? C16 C18 C19 N4 0.2(3) . . . . ? C16 C18 C19 C29 -179.4(3) . . . . ? N6 N5 C20 C25 0.6(3) . . . . ? Mo2 N5 C20 C25 176.53(17) . . . . ? N6 N5 C20 C1 -178.6(2) . . . . ? Mo2 N5 C20 C1 -2.7(4) . . . . ? N2 N1 C21 C22 -1.0(3) . . . . ? Mo1 N1 C21 C22 164.65(18) . . . . ? N2 N1 C21 C27 177.9(2) . . . . ? Mo1 N1 C21 C27 -16.5(4) . . . . ? N2 C15 C22 C21 0.4(3) . . . . ? C28 C15 C22 C21 -179.8(3) . . . . ? N1 C21 C22 C15 0.4(3) . . . . ? C27 C21 C22 C15 -178.4(3) . . . . ? N5 C20 C25 C26 -0.1(3) . . . . ? C1 C20 C25 C26 179.1(3) . . . . ? N5 N6 C26 C25 0.9(3) . . . . ? N5 N6 C26 C24 179.6(2) . . . . ? C20 C25 C26 N6 -0.5(3) . . . . ? C20 C25 C26 C24 -178.9(3) . . . . ? 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 N2 H2N Cl1 0.876(17) 2.679(19) 3.519(2) 161(3) . N4 H4N O1 0.878(17) 1.844(18) 2.713(2) 171(3) . N4 H4N O5 0.878(17) 2.51(3) 2.927(2) 110(2) . N6 H6N O3 0.869(17) 1.978(19) 2.819(3) 163(3) . N6 H6N O5 0.869(17) 2.36(3) 2.795(2) 111(2) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.65 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.245 _refine_diff_density_min -1.464 _refine_diff_density_rms 0.093 # Attachment 'Complex-2.cif' data_ea06709a _database_code_depnum_ccdc_archive 'CCDC 779308' #TrackingRef 'Complex-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 Mo N4 O5' _chemical_formula_sum 'C6 H8 Mo N4 O5' _chemical_formula_weight 312.10 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' Mo Mo -1.6832 0.6857 '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 _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5552(3) _cell_length_b 12.3729(5) _cell_length_c 11.5778(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.3810(10) _cell_angle_gamma 90.00 _cell_volume 1048.38(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9104 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 30.49 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.977 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 1.265 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5713 _exptl_absorpt_correction_T_max 0.6046 _exptl_absorpt_process_details ; SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical X-ray Solutions, Madison, Wisconsin, USA. ; _diffrn_ambient_temperature 173(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-Nonius X8kappa APEX II CCD area detector' ; _diffrn_measurement_method 'phi and omega scans with narrow frames' _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_decay_% 0 _diffrn_reflns_number 25643 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 30.51 _reflns_number_total 3194 _reflns_number_gt 3098 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker (2006). APEX 2. Version 2.1.' _computing_cell_refinement 'Bruker (2006). APEX 2. Version 2.1.' _computing_data_reduction 'Bruker (2006). APEX 2. Version 2.1.' _computing_structure_solution 'Bruker (2006). APEX 2. Version 2.1.' _computing_structure_refinement 'XL, SHELXTL v. 6.14 (Bruker, 2003)' _computing_molecular_graphics 'XP, SHELXTL v. 6.14 (Bruker, 2003)' _computing_publication_material 'XCIF, SHELXTL v. 6.14 (Bruker, 2003)' _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^)+(0.0295P)^2^+0.5786P] 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 3194 _refine_ls_number_parameters 151 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0231 _refine_ls_R_factor_gt 0.0222 _refine_ls_wR_factor_ref 0.0582 _refine_ls_wR_factor_gt 0.0576 _refine_ls_goodness_of_fit_ref 1.158 _refine_ls_restrained_S_all 1.158 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mo1 Mo 0.011710(16) 0.149244(10) 0.330651(11) 0.01764(5) Uani 1 1 d . . . O1 O -0.07561(18) 0.19517(11) 0.44119(11) 0.0298(3) Uani 1 1 d . . . O2 O -0.02562(16) -0.00676(9) 0.34378(10) 0.0226(2) Uani 1 1 d . . . O3 O -0.17193(16) 0.04624(11) 0.25228(11) 0.0288(3) Uani 1 1 d . . . O4 O 0.1158(2) 0.27791(10) 0.27791(12) 0.0318(3) Uani 1 1 d . . . O5 O -0.0684(2) 0.25220(12) 0.20453(12) 0.0367(3) Uani 1 1 d . . . N1 N 0.27695(18) 0.13164(11) 0.45316(12) 0.0196(2) Uani 1 1 d . . . N2 N 0.29515(18) 0.09342(11) 0.56430(12) 0.0205(2) Uani 1 1 d D . . H2N H 0.204(3) 0.0697(17) 0.5906(19) 0.025 Uiso 1 1 d D . . N3 N 0.16641(18) 0.07218(10) 0.19380(12) 0.0199(2) Uani 1 1 d . . . N4 N 0.14194(18) -0.03178(10) 0.15836(12) 0.0202(2) Uani 1 1 d D . . H4N H 0.077(3) -0.0745(16) 0.1914(19) 0.024 Uiso 1 1 d D . . C1 C 0.4697(2) 0.09596(15) 0.62639(15) 0.0268(3) Uani 1 1 d . . . H1 H 0.5156 0.0729 0.7065 0.032 Uiso 1 1 calc R . . C2 C 0.5714(2) 0.13823(15) 0.55312(18) 0.0309(4) Uani 1 1 d . . . H2 H 0.6995 0.1502 0.5720 0.037 Uiso 1 1 calc R . . C3 C 0.4458(2) 0.15934(15) 0.44592(17) 0.0278(3) Uani 1 1 d . . . H3 H 0.4750 0.1891 0.3773 0.033 Uiso 1 1 calc R . . C4 C 0.2105(2) -0.05205(14) 0.06407(15) 0.0255(3) Uani 1 1 d . . . H4 H 0.2067 -0.1191 0.0235 0.031 Uiso 1 1 calc R . . C5 C 0.2871(3) 0.04227(15) 0.03749(16) 0.0292(3) Uani 1 1 d . . . H5 H 0.3482 0.0540 -0.0239 0.035 Uiso 1 1 calc R . . C6 C 0.2558(2) 0.11726(14) 0.12009(15) 0.0255(3) Uani 1 1 d . . . H6 H 0.2931 0.1908 0.1235 0.031 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 Mo1 0.02048(7) 0.01794(7) 0.01471(7) 0.00206(4) 0.00479(5) 0.00458(4) O1 0.0342(6) 0.0333(6) 0.0252(6) -0.0014(5) 0.0135(5) 0.0073(5) O2 0.0229(5) 0.0228(5) 0.0226(5) 0.0014(4) 0.0067(4) -0.0030(4) O3 0.0215(5) 0.0414(7) 0.0207(5) 0.0000(5) 0.0001(4) -0.0030(5) O4 0.0501(8) 0.0183(5) 0.0292(6) 0.0051(5) 0.0143(6) 0.0014(5) O5 0.0452(8) 0.0356(7) 0.0278(6) 0.0129(5) 0.0062(6) 0.0177(6) N1 0.0192(6) 0.0222(6) 0.0174(6) 0.0007(5) 0.0045(4) -0.0031(4) N2 0.0179(5) 0.0254(6) 0.0178(6) 0.0016(5) 0.0036(4) -0.0012(5) N3 0.0248(6) 0.0173(5) 0.0186(6) 0.0001(4) 0.0069(5) -0.0009(4) N4 0.0234(6) 0.0179(5) 0.0203(6) -0.0008(4) 0.0073(5) -0.0006(4) C1 0.0212(7) 0.0336(8) 0.0224(7) -0.0018(6) -0.0005(6) 0.0003(6) C2 0.0202(7) 0.0392(9) 0.0328(9) -0.0076(7) 0.0059(6) -0.0072(6) C3 0.0235(7) 0.0335(8) 0.0284(8) -0.0021(6) 0.0106(6) -0.0091(6) C4 0.0280(7) 0.0270(7) 0.0224(7) -0.0045(6) 0.0081(6) 0.0029(6) C5 0.0326(8) 0.0346(9) 0.0245(8) -0.0013(7) 0.0149(6) 0.0001(7) C6 0.0324(8) 0.0233(7) 0.0237(7) 0.0012(6) 0.0124(6) -0.0041(6) _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 Mo1 O1 1.6778(12) . ? Mo1 O5 1.9189(13) . ? Mo1 O3 1.9357(12) . ? Mo1 O4 1.9401(13) . ? Mo1 O2 1.9620(12) . ? Mo1 N1 2.1594(13) . ? Mo1 N3 2.3886(13) . ? O2 O3 1.4807(16) . ? O4 O5 1.474(2) . ? N1 C3 1.344(2) . ? N1 N2 1.3454(18) . ? N2 C1 1.337(2) . ? N2 H2N 0.873(15) . ? N3 C6 1.335(2) . ? N3 N4 1.3488(17) . ? N4 C4 1.343(2) . ? N4 H4N 0.873(15) . ? C1 C2 1.381(3) . ? C1 H1 0.9500 . ? C2 C3 1.387(3) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C5 1.371(2) . ? C4 H4 0.9500 . ? C5 C6 1.394(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? 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 Mo1 O5 104.25(6) . . ? O1 Mo1 O3 102.04(6) . . ? O5 Mo1 O3 91.52(6) . . ? O1 Mo1 O4 103.24(6) . . ? O5 Mo1 O4 44.90(6) . . ? O3 Mo1 O4 133.79(6) . . ? O1 Mo1 O2 100.53(6) . . ? O5 Mo1 O2 133.46(6) . . ? O3 Mo1 O2 44.65(5) . . ? O4 Mo1 O2 155.36(5) . . ? O1 Mo1 N1 90.55(6) . . ? O5 Mo1 N1 129.25(6) . . ? O3 Mo1 N1 132.97(5) . . ? O4 Mo1 N1 84.66(6) . . ? O2 Mo1 N1 88.72(5) . . ? O1 Mo1 N3 172.30(5) . . ? O5 Mo1 N3 82.77(5) . . ? O3 Mo1 N3 80.68(5) . . ? O4 Mo1 N3 79.37(5) . . ? O2 Mo1 N3 76.24(5) . . ? N1 Mo1 N3 82.43(5) . . ? O3 O2 Mo1 66.73(7) . . ? O2 O3 Mo1 68.62(6) . . ? O5 O4 Mo1 66.79(7) . . ? O4 O5 Mo1 68.31(7) . . ? C3 N1 N2 106.03(13) . . ? C3 N1 Mo1 132.37(12) . . ? N2 N1 Mo1 121.43(10) . . ? C1 N2 N1 111.04(13) . . ? C1 N2 H2N 125.6(15) . . ? N1 N2 H2N 123.4(15) . . ? C6 N3 N4 104.89(13) . . ? C6 N3 Mo1 131.75(11) . . ? N4 N3 Mo1 121.99(10) . . ? C4 N4 N3 111.96(13) . . ? C4 N4 H4N 128.0(14) . . ? N3 N4 H4N 119.6(14) . . ? N2 C1 C2 107.67(15) . . ? N2 C1 H1 126.2 . . ? C2 C1 H1 126.2 . . ? C1 C2 C3 105.07(15) . . ? C1 C2 H2 127.5 . . ? C3 C2 H2 127.5 . . ? N1 C3 C2 110.18(16) . . ? N1 C3 H3 124.9 . . ? C2 C3 H3 124.9 . . ? N4 C4 C5 107.03(14) . . ? N4 C4 H4 126.5 . . ? C5 C4 H4 126.5 . . ? C4 C5 C6 105.05(14) . . ? C4 C5 H5 127.5 . . ? C6 C5 H5 127.5 . . ? N3 C6 C5 111.06(15) . . ? N3 C6 H6 124.5 . . ? C5 C6 H6 124.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Mo1 O2 O3 96.54(8) . . . . ? O5 Mo1 O2 O3 -24.86(11) . . . . ? O4 Mo1 O2 O3 -98.91(14) . . . . ? N1 Mo1 O2 O3 -173.14(7) . . . . ? N3 Mo1 O2 O3 -90.62(7) . . . . ? O1 Mo1 O3 O2 -92.86(8) . . . . ? O5 Mo1 O3 O2 162.22(8) . . . . ? O4 Mo1 O3 O2 145.21(8) . . . . ? N1 Mo1 O3 O2 9.40(10) . . . . ? N3 Mo1 O3 O2 79.81(7) . . . . ? O1 Mo1 O4 O5 -97.01(9) . . . . ? O3 Mo1 O4 O5 24.48(11) . . . . ? O2 Mo1 O4 O5 98.59(14) . . . . ? N1 Mo1 O4 O5 173.67(8) . . . . ? N3 Mo1 O4 O5 90.40(8) . . . . ? O1 Mo1 O5 O4 94.58(9) . . . . ? O3 Mo1 O5 O4 -162.59(8) . . . . ? O2 Mo1 O5 O4 -145.39(8) . . . . ? N1 Mo1 O5 O4 -8.15(11) . . . . ? N3 Mo1 O5 O4 -82.18(8) . . . . ? O1 Mo1 N1 C3 -134.09(16) . . . . ? O5 Mo1 N1 C3 -25.08(19) . . . . ? O3 Mo1 N1 C3 118.80(15) . . . . ? O4 Mo1 N1 C3 -30.85(16) . . . . ? O2 Mo1 N1 C3 125.39(16) . . . . ? N3 Mo1 N1 C3 49.10(16) . . . . ? O1 Mo1 N1 N2 40.46(12) . . . . ? O5 Mo1 N1 N2 149.47(11) . . . . ? O3 Mo1 N1 N2 -66.65(14) . . . . ? O4 Mo1 N1 N2 143.70(12) . . . . ? O2 Mo1 N1 N2 -60.06(12) . . . . ? N3 Mo1 N1 N2 -136.35(12) . . . . ? C3 N1 N2 C1 -0.24(19) . . . . ? Mo1 N1 N2 C1 -176.05(11) . . . . ? O5 Mo1 N3 C6 40.11(15) . . . . ? O3 Mo1 N3 C6 132.85(15) . . . . ? O4 Mo1 N3 C6 -5.25(15) . . . . ? O2 Mo1 N3 C6 178.26(16) . . . . ? N1 Mo1 N3 C6 -91.21(15) . . . . ? O5 Mo1 N3 N4 -124.35(12) . . . . ? O3 Mo1 N3 N4 -31.61(11) . . . . ? O4 Mo1 N3 N4 -169.71(12) . . . . ? O2 Mo1 N3 N4 13.80(11) . . . . ? N1 Mo1 N3 N4 104.33(12) . . . . ? C6 N3 N4 C4 -1.00(18) . . . . ? Mo1 N3 N4 C4 167.06(10) . . . . ? N1 N2 C1 C2 0.3(2) . . . . ? N2 C1 C2 C3 -0.2(2) . . . . ? N2 N1 C3 C2 0.1(2) . . . . ? Mo1 N1 C3 C2 175.28(12) . . . . ? C1 C2 C3 N1 0.0(2) . . . . ? N3 N4 C4 C5 1.25(19) . . . . ? N4 C4 C5 C6 -0.9(2) . . . . ? N4 N3 C6 C5 0.36(19) . . . . ? Mo1 N3 C6 C5 -166.04(12) . . . . ? C4 C5 C6 N3 0.4(2) . . . . ? 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 N2 H2N O2 0.873(15) 1.871(16) 2.7397(17) 173(2) 3_556 N2 H2N O3 0.873(15) 2.375(19) 3.0569(19) 135.2(19) 3_556 N4 H4N O2 0.873(15) 2.26(2) 2.7671(18) 117.2(17) . N4 H4N O4 0.873(15) 2.415(16) 3.2547(19) 161.5(19) 2_545 N4 H4N O5 0.873(15) 2.468(18) 3.226(2) 145.7(19) 2_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.384 _refine_diff_density_min -0.890 _refine_diff_density_rms 0.095