Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2008 _publ_contact_author_name 'Z.-H. Zhou' _publ_contact_author_address ; Chemstry State Key Laboratory for Physical Chemistry of Solid Surfaces Xiamen University Xiamen 361005 CHINA ; _publ_contact_author_email ZHZHOU@XMU.EDU.CN _publ_section_title ; N-Heterocycle Chelated Oxomolybdenum(VI and V) Complexes with Bidentate Citrate ; loop_ _publ_author_name 'Z.-H. Zhou' 'Ze-Xing Cao.' 'Can-Yu Chen.' 'Yuan L.Chow' 'Khi-Rui Tsai.' data_1 _database_code_depnum_ccdc_archive 'CCDC 673570' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Citrato phenanthroline molybdate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 Mo2 N2 O15' _chemical_formula_weight 696.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mo Mo -1.6832 0.6857 '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 7.6946(6) _cell_length_b 11.7676(10) _cell_length_c 13.7413(11) _cell_angle_alpha 87.550(2) _cell_angle_beta 76.4780(10) _cell_angle_gamma 71.122(2) _cell_volume 1143.94(16) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.021 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.179 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.8070 _exptl_absorpt_correction_T_max 0.9543 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 Apex CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6172 _diffrn_reflns_av_R_equivalents 0.1143 _diffrn_reflns_av_sigmaI/netI 0.1147 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3816 _reflns_number_gt 2984 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0555P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3816 _refine_ls_number_parameters 358 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.043 _refine_ls_shift/su_mean 0.003 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 -0.02320(9) 0.30549(6) 0.79635(4) 0.0166(2) Uani 1 1 d . . . Mo2 Mo 0.20911(9) 0.52363(6) 0.84272(4) 0.0162(2) Uani 1 1 d . . . O1 O -0.0024(7) 0.1366(4) 0.7947(3) 0.0160(11) Uani 1 1 d . . . O2 O 0.2802(7) 0.2097(4) 0.7365(4) 0.0197(12) Uani 1 1 d . . . O3 O 0.4830(8) 0.0312(5) 0.6727(5) 0.0388(16) Uani 1 1 d . . . O4 O 0.3285(9) 0.0184(5) 0.9010(5) 0.0405(17) Uani 1 1 d . . . O5 O 0.2315(10) -0.1356(6) 0.9507(5) 0.0426(17) Uani 1 1 d D . . O6 O -0.0414(10) -0.1077(6) 0.6377(6) 0.058(2) Uani 1 1 d . . . O7 O -0.2065(10) 0.0845(6) 0.6467(6) 0.0517(19) Uani 1 1 d D . . O8 O -0.2452(8) 0.3460(5) 0.8731(4) 0.0283(14) Uani 1 1 d . . . O9 O -0.0593(9) 0.3400(5) 0.6802(4) 0.0322(15) Uani 1 1 d . . . O10 O 0.2614(8) 0.4788(5) 0.9542(4) 0.0281(14) Uani 1 1 d . . . O11 O 0.0578(8) 0.6667(4) 0.8673(4) 0.0229(13) Uani 1 1 d . . . O12 O 0.0629(7) 0.4384(4) 0.8144(3) 0.0151(11) Uani 1 1 d . . . N1 N 0.4475(9) 0.5960(5) 0.8067(4) 0.0185(14) Uani 1 1 d . . . N2 N 0.2637(10) 0.5644(5) 0.6754(4) 0.0208(15) Uani 1 1 d . . . C1 C 0.1563(11) 0.0502(7) 0.7341(5) 0.0217(18) Uani 1 1 d . . . C2 C 0.3228(12) 0.0999(7) 0.7134(6) 0.0207(18) Uani 1 1 d . . . C3 C 0.2005(12) -0.0667(7) 0.7898(6) 0.030(2) Uani 1 1 d . . . H3A H 0.0885 -0.0927 0.8055 0.037 Uiso 1 1 calc R . . H3B H 0.3022 -0.1288 0.7457 0.037 Uiso 1 1 calc R . . C4 C 0.2589(12) -0.0563(7) 0.8856(6) 0.027(2) Uani 1 1 d . . . C5 C 0.1183(12) 0.0334(8) 0.6310(5) 0.027(2) Uani 1 1 d . . . H5A H 0.1009 0.1092 0.5961 0.033 Uiso 1 1 calc R . . H5B H 0.2287 -0.0274 0.5907 0.033 Uiso 1 1 calc R . . C6 C -0.0522(13) -0.0045(8) 0.6396(6) 0.0260(19) Uani 1 1 d . . . C7 C 0.5333(11) 0.6138(7) 0.8743(6) 0.0238(19) Uani 1 1 d . . . H7A H 0.5030 0.5858 0.9391 0.029 Uiso 1 1 calc R . . C8 C 0.6667(12) 0.6724(7) 0.8529(6) 0.0257(19) Uani 1 1 d . . . H8A H 0.7229 0.6853 0.9034 0.031 Uiso 1 1 calc R . . C9 C 0.7169(12) 0.7113(7) 0.7594(6) 0.030(2) Uani 1 1 d . . . H9A H 0.8094 0.7497 0.7450 0.036 Uiso 1 1 calc R . . C10 C 0.6314(11) 0.6943(7) 0.6846(6) 0.0240(19) Uani 1 1 d . . . C11 C 0.6638(12) 0.7375(7) 0.5856(6) 0.030(2) Uani 1 1 d . . . H11A H 0.7551 0.7762 0.5653 0.036 Uiso 1 1 calc R . . C12 C 0.5621(13) 0.7228(7) 0.5197(6) 0.034(2) Uani 1 1 d . . . H12A H 0.5841 0.7531 0.4552 0.041 Uiso 1 1 calc R . . C13 C 0.4275(12) 0.6644(7) 0.5460(6) 0.026(2) Uani 1 1 d . . . C14 C 0.3133(13) 0.6510(7) 0.4829(6) 0.031(2) Uani 1 1 d . . . H14A H 0.3252 0.6826 0.4186 0.037 Uiso 1 1 calc R . . C15 C 0.1860(13) 0.5920(7) 0.5164(6) 0.029(2) Uani 1 1 d . . . H15A H 0.1139 0.5795 0.4738 0.035 Uiso 1 1 calc R . . C16 C 0.1623(12) 0.5502(7) 0.6130(5) 0.0236(18) Uani 1 1 d . . . H16A H 0.0723 0.5108 0.6351 0.028 Uiso 1 1 calc R . . C17 C 0.3935(11) 0.6199(6) 0.6421(5) 0.0165(17) Uani 1 1 d . . . C18 C 0.4958(11) 0.6358(6) 0.7117(5) 0.0187(17) Uani 1 1 d . . . O1W O 0.0993(8) 0.2529(5) 0.9357(4) 0.0243(13) Uani 1 1 d D . . O2W O 0.4594(8) 0.3615(4) 0.7717(4) 0.0224(13) Uani 1 1 d D . . O3W O 0.3653(12) -0.1248(7) 1.1109(5) 0.057(2) Uani 1 1 d D . . H1 H 0.243(16) -0.209(3) 0.943(8) 0.068 Uiso 1 1 d D . . H2 H -0.302(9) 0.060(9) 0.661(8) 0.068 Uiso 1 1 d D . . H1W1 H 0.065(14) 0.191(5) 0.942(6) 0.068 Uiso 1 1 d D . . H1W2 H 0.117(14) 0.272(7) 0.991(3) 0.068 Uiso 1 1 d D . . H2W1 H 0.420(12) 0.306(5) 0.759(7) 0.068 Uiso 1 1 d D . . H2W2 H 0.542(11) 0.335(7) 0.806(7) 0.068 Uiso 1 1 d D . . H3W1 H 0.341(16) -0.0489(18) 1.109(7) 0.068 Uiso 1 1 d D . . H3W2 H 0.328(15) -0.149(7) 1.065(6) 0.068 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mo1 0.0167(4) 0.0160(4) 0.0162(3) 0.0011(3) -0.0070(3) -0.0019(3) Mo2 0.0176(4) 0.0180(4) 0.0115(3) -0.0006(3) -0.0047(3) -0.0027(3) O1 0.015(3) 0.014(3) 0.016(2) 0.001(2) 0.000(2) -0.002(2) O2 0.016(3) 0.017(3) 0.022(3) -0.003(2) -0.003(2) 0.000(2) O3 0.014(4) 0.039(4) 0.058(4) -0.021(3) 0.000(3) -0.006(3) O4 0.056(5) 0.015(3) 0.058(4) 0.004(3) -0.036(4) -0.006(3) O5 0.051(5) 0.038(4) 0.042(4) 0.004(3) -0.009(3) -0.020(4) O6 0.027(4) 0.042(5) 0.110(6) -0.007(4) -0.025(4) -0.010(3) O7 0.022(4) 0.034(4) 0.103(6) -0.006(4) -0.020(4) -0.009(3) O8 0.022(4) 0.021(3) 0.035(3) -0.002(2) -0.004(3) 0.002(3) O9 0.039(4) 0.035(4) 0.027(3) 0.002(3) -0.021(3) -0.010(3) O10 0.028(4) 0.042(4) 0.016(3) 0.001(2) -0.009(2) -0.009(3) O11 0.022(3) 0.020(3) 0.022(3) -0.006(2) -0.006(2) 0.001(2) O12 0.022(3) 0.015(3) 0.015(2) 0.005(2) -0.008(2) -0.013(2) N1 0.022(4) 0.015(3) 0.017(3) 0.003(3) -0.005(3) -0.005(3) N2 0.031(4) 0.017(3) 0.009(3) -0.002(2) -0.004(3) 0.000(3) C1 0.021(5) 0.021(4) 0.022(4) -0.005(3) -0.006(3) -0.004(4) C2 0.017(5) 0.024(5) 0.023(4) 0.002(3) -0.008(3) -0.007(4) C3 0.023(5) 0.018(4) 0.050(5) -0.008(4) -0.011(4) -0.002(4) C4 0.026(5) 0.012(4) 0.032(5) 0.002(4) -0.007(4) 0.009(4) C5 0.029(5) 0.036(5) 0.017(4) -0.010(4) -0.002(4) -0.012(4) C6 0.029(6) 0.034(5) 0.022(4) -0.006(4) -0.009(4) -0.016(4) C7 0.019(5) 0.018(4) 0.028(4) 0.000(3) -0.012(4) 0.005(4) C8 0.023(5) 0.028(5) 0.028(4) 0.003(4) -0.009(4) -0.009(4) C9 0.027(5) 0.023(5) 0.040(5) 0.001(4) -0.008(4) -0.007(4) C10 0.014(5) 0.016(4) 0.036(5) -0.002(3) -0.005(4) 0.003(3) C11 0.025(5) 0.031(5) 0.032(5) 0.003(4) 0.001(4) -0.011(4) C12 0.035(6) 0.024(5) 0.033(5) 0.017(4) 0.004(4) -0.006(4) C13 0.033(6) 0.015(4) 0.023(4) -0.001(3) -0.008(4) 0.001(4) C14 0.046(6) 0.026(5) 0.014(4) 0.007(3) -0.003(4) -0.005(4) C15 0.036(6) 0.022(5) 0.020(4) 0.002(3) -0.013(4) 0.005(4) C16 0.025(5) 0.024(5) 0.021(4) 0.001(3) -0.009(4) -0.006(4) C17 0.017(5) 0.016(4) 0.011(3) -0.003(3) 0.000(3) 0.001(3) C18 0.020(5) 0.011(4) 0.021(4) 0.001(3) -0.005(3) -0.001(3) O1W 0.032(4) 0.026(3) 0.017(3) 0.001(2) -0.012(3) -0.007(3) O2W 0.023(4) 0.018(3) 0.025(3) 0.003(2) -0.011(2) -0.001(2) O3W 0.070(6) 0.066(5) 0.042(4) 0.003(4) -0.021(4) -0.026(5) _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 O9 1.694(5) . ? Mo1 O8 1.712(6) . ? Mo1 O12 1.931(5) . ? Mo1 O1 1.943(5) . ? Mo1 O2 2.208(5) 1 ? Mo1 O2 2.208(5) . ? Mo1 O1W 2.303(5) . ? Mo2 O10 1.694(5) . ? Mo2 O11 1.703(5) . ? Mo2 O12 1.841(5) . ? Mo2 N1 2.211(7) . ? Mo2 O2W 2.281(5) . ? Mo2 N2 2.297(6) . ? O1 C1 1.419(8) . ? O2 O2 0.000(15) 1 ? O2 C2 1.261(9) . ? O3 C2 1.247(9) . ? O4 O4 0.000(13) 1 ? O4 C4 1.215(10) . ? O5 O5 0.000(17) 1 ? O5 C4 1.297(10) . ? O6 C6 1.191(10) . ? O7 C6 1.291(11) . ? N1 C7 1.317(9) . ? N1 C18 1.377(9) . ? N2 C16 1.336(9) . ? N2 C17 1.347(10) . ? C1 C3 1.524(11) . ? C1 C2 1.537(11) . ? C1 C5 1.544(9) . ? C2 O2 1.261(9) 1 ? C3 C4 1.508(11) . ? C4 O4 1.215(10) 1 ? C4 O5 1.297(10) 1 ? C5 C6 1.495(12) . ? C7 C8 1.384(12) . ? C8 C9 1.357(11) . ? C9 C10 1.397(11) . ? C10 C18 1.401(11) . ? C10 C11 1.427(11) . ? C11 C12 1.376(11) . ? C12 C13 1.393(12) . ? C13 C17 1.398(10) . ? C13 C14 1.416(11) . ? C14 C15 1.362(13) . ? C15 C16 1.388(10) . ? C17 C18 1.425(10) . ? 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 O9 Mo1 O8 104.5(3) . . ? O9 Mo1 O12 96.4(2) . . ? O8 Mo1 O12 103.0(2) . . ? O9 Mo1 O1 99.4(2) . . ? O8 Mo1 O1 92.8(2) . . ? O12 Mo1 O1 154.0(2) . . ? O9 Mo1 O2 92.2(2) . 1 ? O8 Mo1 O2 160.9(2) . 1 ? O12 Mo1 O2 83.8(2) . 1 ? O1 Mo1 O2 75.1(2) . 1 ? O9 Mo1 O2 92.2(2) . . ? O8 Mo1 O2 160.9(2) . . ? O12 Mo1 O2 83.8(2) . . ? O1 Mo1 O2 75.1(2) . . ? O2 Mo1 O2 0.0(4) 1 . ? O9 Mo1 O1W 166.4(3) . . ? O8 Mo1 O1W 88.8(2) . . ? O12 Mo1 O1W 77.66(19) . . ? O1 Mo1 O1W 82.25(19) . . ? O2 Mo1 O1W 75.11(19) 1 . ? O2 Mo1 O1W 75.11(19) . . ? O10 Mo2 O11 104.1(2) . . ? O10 Mo2 O12 107.8(2) . . ? O11 Mo2 O12 104.2(2) . . ? O10 Mo2 N1 89.9(2) . . ? O11 Mo2 N1 89.0(2) . . ? O12 Mo2 N1 154.1(2) . . ? O10 Mo2 O2W 87.0(2) . . ? O11 Mo2 O2W 162.1(2) . . ? O12 Mo2 O2W 85.2(2) . . ? N1 Mo2 O2W 76.8(2) . . ? O10 Mo2 N2 157.6(3) . . ? O11 Mo2 N2 88.7(2) . . ? O12 Mo2 N2 86.1(2) . . ? N1 Mo2 N2 71.8(2) . . ? O2W Mo2 N2 76.6(2) . . ? C1 O1 Mo1 121.3(5) . . ? O2 O2 C2 0(10) 1 . ? O2 O2 Mo1 0(10) 1 . ? C2 O2 Mo1 115.8(5) . . ? O4 O4 C4 0(10) 1 . ? O5 O5 C4 0(10) 1 . ? Mo2 O12 Mo1 160.8(3) . . ? C7 N1 C18 118.3(7) . . ? C7 N1 Mo2 123.0(5) . . ? C18 N1 Mo2 118.4(5) . . ? C16 N2 C17 118.3(6) . . ? C16 N2 Mo2 124.9(6) . . ? C17 N2 Mo2 116.4(5) . . ? O1 C1 C3 108.5(6) . . ? O1 C1 C2 108.1(6) . . ? C3 C1 C2 111.3(6) . . ? O1 C1 C5 110.4(6) . . ? C3 C1 C5 112.3(7) . . ? C2 C1 C5 106.2(6) . . ? O3 C2 O2 126.3(8) . 1 ? O3 C2 O2 126.3(8) . . ? O2 C2 O2 0.0(4) 1 . ? O3 C2 C1 118.4(7) . . ? O2 C2 C1 115.3(7) 1 . ? O2 C2 C1 115.3(7) . . ? C4 C3 C1 113.5(7) . . ? O4 C4 O4 0.0(7) 1 . ? O4 C4 O5 122.2(8) 1 1 ? O4 C4 O5 122.2(8) . 1 ? O4 C4 O5 122.2(8) 1 . ? O4 C4 O5 122.2(8) . . ? O5 C4 O5 0.0(7) 1 . ? O4 C4 C3 123.5(8) 1 . ? O4 C4 C3 123.5(8) . . ? O5 C4 C3 114.3(8) 1 . ? O5 C4 C3 114.3(8) . . ? C6 C5 C1 112.5(7) . . ? O6 C6 O7 124.7(8) . . ? O6 C6 C5 121.8(8) . . ? O7 C6 C5 113.5(8) . . ? N1 C7 C8 122.1(8) . . ? C9 C8 C7 120.4(8) . . ? C8 C9 C10 120.0(9) . . ? C9 C10 C18 116.6(8) . . ? C9 C10 C11 125.1(8) . . ? C18 C10 C11 118.1(7) . . ? C12 C11 C10 120.4(8) . . ? C11 C12 C13 121.8(8) . . ? C12 C13 C17 119.3(8) . . ? C12 C13 C14 124.3(8) . . ? C17 C13 C14 116.4(8) . . ? C15 C14 C13 119.3(7) . . ? C14 C15 C16 120.4(8) . . ? N2 C16 C15 121.8(8) . . ? N2 C17 C13 123.8(7) . . ? N2 C17 C18 116.6(6) . . ? C13 C17 C18 119.6(7) . . ? N1 C18 C10 122.6(7) . . ? N1 C18 C17 116.5(7) . . ? C10 C18 C17 120.8(7) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1W1 O4 0.849(10) 2.33(10) 2.744(8) 110(8) 1 O2W H2W1 O2 0.849(10) 1.87(2) 2.703(8) 167(9) 1 O3W H3W2 O5 0.849(10) 1.87(4) 2.663(9) 156(8) 1 O7 H2 O3 0.852(10) 1.77(3) 2.604(9) 168(11) 1_455 _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 1.802 _refine_diff_density_min -0.781 _refine_diff_density_rms 0.178 # Attachment 'cif2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 673571' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Citrato bipyridine molybdate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H36 Mo2 N4 O21' _chemical_formula_weight 1004.53 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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.306(3) _cell_length_b 13.089(5) _cell_length_c 16.049(9) _cell_angle_alpha 103.71(4) _cell_angle_beta 107.11(4) _cell_angle_gamma 94.48(3) _cell_volume 1984.6(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.721 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.8693 _exptl_absorpt_correction_T_max 0.8693 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24574 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_sigmaI/netI 0.1983 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 32.50 _reflns_number_total 12584 _reflns_number_gt 5116 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0661P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12584 _refine_ls_number_parameters 565 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.1416 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1514 _refine_ls_wR_factor_gt 0.1247 _refine_ls_goodness_of_fit_ref 0.893 _refine_ls_restrained_S_all 0.892 _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 Mo1 Mo 0.24359(4) 0.35256(3) 0.17366(3) 0.03983(12) Uani 1 1 d . . . Mo2 Mo 0.01733(4) 0.26261(3) 0.29619(3) 0.04258(13) Uani 1 1 d . . . N1 N 0.1785(4) 0.5165(3) 0.1945(3) 0.0526(10) Uani 1 1 d . . . N2 N 0.0172(4) 0.3417(3) 0.0793(3) 0.0502(10) Uani 1 1 d . . . N11 N -0.0685(4) 0.4167(3) 0.3031(3) 0.0463(9) Uani 1 1 d . . . N12 N 0.1686(4) 0.3985(3) 0.4163(3) 0.0501(10) Uani 1 1 d . . . O1 O 0.2691(3) 0.2064(2) 0.1173(2) 0.0453(7) Uani 1 1 d . . . O2 O 0.2832(3) 0.3711(3) 0.0581(2) 0.0552(8) Uani 1 1 d . . . O3 O 0.3849(5) 0.3038(4) -0.0430(3) 0.1007(15) Uani 1 1 d . . . O4 O 0.5724(5) 0.1928(4) 0.2616(4) 0.1059(16) Uani 1 1 d . . . O5 O 0.5048(9) 0.0432(5) 0.1448(4) 0.139(2) Uani 1 1 d D . . O6 O 0.0957(5) 0.1543(4) -0.1004(3) 0.1012(15) Uani 1 1 d . . . O7 O 0.0708(6) -0.0043(4) -0.0767(3) 0.1049(16) Uani 1 1 d D . . O8 O 0.3939(3) 0.4117(3) 0.2532(3) 0.0703(10) Uani 1 1 d . . . O9 O 0.1435(3) 0.3025(2) 0.24037(19) 0.0439(7) Uani 1 1 d . . . O11 O 0.1212(3) 0.1518(2) 0.3344(2) 0.0432(7) Uani 1 1 d . . . O12 O -0.0512(3) 0.2417(2) 0.4014(2) 0.0487(8) Uani 1 1 d . . . O13 O -0.0750(3) 0.1294(3) 0.4815(2) 0.0599(9) Uani 1 1 d . . . O14 O 0.3372(4) -0.0002(4) 0.4022(4) 0.0929(14) Uani 1 1 d . . . O15 O 0.4443(4) 0.1597(4) 0.4901(4) 0.0934(14) Uani 1 1 d D . . O16 O -0.1994(4) 0.0098(3) 0.2715(3) 0.0903(14) Uani 1 1 d . . . O17 O -0.1626(6) -0.1519(4) 0.2865(5) 0.122(2) Uani 1 1 d D . . O18 O -0.1241(3) 0.2060(3) 0.2062(2) 0.0568(8) Uani 1 1 d . . . C1 C 0.3481(5) 0.1993(4) 0.0566(3) 0.0589(13) Uani 1 1 d . . . C2 C 0.3387(5) 0.2971(5) 0.0168(3) 0.0591(13) Uani 1 1 d . . . C3 C 0.5027(6) 0.2101(6) 0.1102(5) 0.085(2) Uani 1 1 d . . . H3A H 0.5510 0.1852 0.0676 0.102 Uiso 1 1 calc R . . H3B H 0.5387 0.2850 0.1394 0.102 Uiso 1 1 calc R . . C4 C 0.5347(7) 0.1490(6) 0.1825(5) 0.0845(19) Uani 1 1 d . . . C5 C 0.2962(7) 0.0926(5) -0.0181(4) 0.0801(18) Uani 1 1 d . . . H5A H 0.3496 0.0874 -0.0592 0.096 Uiso 1 1 calc R . . H5B H 0.3088 0.0339 0.0093 0.096 Uiso 1 1 calc R . . C6 C 0.1492(7) 0.0846(5) -0.0693(3) 0.0681(16) Uani 1 1 d . . . C7 C 0.2641(7) 0.6010(4) 0.2531(4) 0.0792(18) Uani 1 1 d . . . H7A H 0.3497 0.5908 0.2873 0.095 Uiso 1 1 calc R . . C8 C 0.2331(9) 0.7053(5) 0.2668(5) 0.097(2) Uani 1 1 d . . . H8A H 0.2945 0.7630 0.3095 0.116 Uiso 1 1 calc R . . C9 C 0.1062(10) 0.7168(6) 0.2131(5) 0.111(3) Uani 1 1 d . . . H9A H 0.0815 0.7843 0.2194 0.133 Uiso 1 1 calc R . . C10 C 0.0152(7) 0.6311(4) 0.1503(4) 0.0772(17) Uani 1 1 d . . . H10A H -0.0689 0.6398 0.1131 0.093 Uiso 1 1 calc R . . C11 C 0.0544(6) 0.5301(4) 0.1448(4) 0.0590(14) Uani 1 1 d . . . C12 C -0.0373(5) 0.4321(4) 0.0820(3) 0.0498(11) Uani 1 1 d . . . C13 C -0.1756(6) 0.4295(6) 0.0286(4) 0.0761(18) Uani 1 1 d . . . H13A H -0.2127 0.4919 0.0277 0.091 Uiso 1 1 calc R . . C14 C -0.2517(6) 0.3332(7) -0.0209(4) 0.087(2) Uani 1 1 d . . . H14A H -0.3432 0.3289 -0.0550 0.105 Uiso 1 1 calc R . . C15 C -0.1936(7) 0.2410(6) -0.0207(5) 0.0847(19) Uani 1 1 d . . . H15A H -0.2452 0.1752 -0.0558 0.102 Uiso 1 1 calc R . . C16 C -0.0606(5) 0.2474(4) 0.0309(3) 0.0583(14) Uani 1 1 d . . . H16A H -0.0231 0.1853 0.0326 0.070 Uiso 1 1 calc R . . C21 C 0.0838(4) 0.0996(3) 0.3951(3) 0.0415(10) Uani 1 1 d . . . C22 C -0.0227(5) 0.1586(4) 0.4299(3) 0.0474(11) Uani 1 1 d . . . C23 C 0.2102(5) 0.1146(4) 0.4802(4) 0.0585(13) Uani 1 1 d . . . H23A H 0.1893 0.0707 0.5170 0.070 Uiso 1 1 calc R . . H23B H 0.2297 0.1883 0.5160 0.070 Uiso 1 1 calc R . . C24 C 0.3394(6) 0.0841(5) 0.4552(4) 0.0626(14) Uani 1 1 d . . . C25 C 0.0277(5) -0.0188(4) 0.3499(4) 0.0574(13) Uani 1 1 d . . . H25A H 0.0773 -0.0449 0.3085 0.069 Uiso 1 1 calc R . . H25B H 0.0493 -0.0561 0.3966 0.069 Uiso 1 1 calc R . . C26 C -0.1196(6) -0.0488(4) 0.2999(4) 0.0636(15) Uani 1 1 d . . . C27 C -0.1905(5) 0.4212(5) 0.2451(4) 0.0617(14) Uani 1 1 d . . . H27A H -0.2382 0.3587 0.2013 0.074 Uiso 1 1 calc R . . C28 C -0.2493(6) 0.5106(5) 0.2461(4) 0.0751(17) Uani 1 1 d . . . H28A H -0.3337 0.5089 0.2034 0.090 Uiso 1 1 calc R . . C29 C -0.1819(7) 0.6039(5) 0.3114(5) 0.0845(19) Uani 1 1 d . . . H29A H -0.2198 0.6664 0.3136 0.101 Uiso 1 1 calc R . . C30 C -0.0550(7) 0.6024(4) 0.3744(4) 0.0727(16) Uani 1 1 d . . . H30A H -0.0077 0.6641 0.4193 0.087 Uiso 1 1 calc R . . C31 C 0.0003(5) 0.5077(4) 0.3693(3) 0.0523(12) Uani 1 1 d . . . C32 C 0.1322(5) 0.4973(4) 0.4336(3) 0.0499(11) Uani 1 1 d . . . C33 C 0.2162(6) 0.5813(5) 0.5066(4) 0.0723(17) Uani 1 1 d . . . H33A H 0.1889 0.6479 0.5180 0.087 Uiso 1 1 calc R . . C34 C 0.3377(6) 0.5649(5) 0.5604(5) 0.0778(18) Uani 1 1 d . . . H34A H 0.3941 0.6203 0.6085 0.093 Uiso 1 1 calc R . . C35 C 0.3763(5) 0.4662(5) 0.5432(4) 0.0705(17) Uani 1 1 d . . . H35A H 0.4575 0.4532 0.5807 0.085 Uiso 1 1 calc R . . C36 C 0.2896(5) 0.3836(5) 0.4668(4) 0.0628(14) Uani 1 1 d . . . H36A H 0.3186 0.3181 0.4520 0.075 Uiso 1 1 calc R . . O1W O -0.1965(5) -0.0418(4) -0.1856(3) 0.0878(13) Uani 1 1 d D . . O2W O 0.6413(5) 0.1234(6) 0.4203(4) 0.1161(19) Uani 1 1 d D . . O3W O 0.4610(9) -0.0684(6) 0.2617(5) 0.166(3) Uani 1 1 d D . . O4W O -0.4202(7) -0.2369(7) 0.2079(6) 0.186(4) Uani 1 1 d D . . H1 H 0.478(13) -0.023(2) 0.134(9) 0.223 Uiso 1 1 d D . . H2 H 0.003(8) -0.037(9) -0.123(5) 0.223 Uiso 1 1 d D . . H11 H 0.520(6) 0.144(9) 0.483(8) 0.223 Uiso 1 1 d D . . H12 H -0.136(12) -0.210(5) 0.265(8) 0.223 Uiso 1 1 d D . . H1W2 H -0.163(9) -0.048(10) -0.228(4) 0.223 Uiso 1 1 d D . . H2W1 H 0.647(12) 0.136(9) 0.372(4) 0.223 Uiso 1 1 d D . . H2W2 H 0.705(9) 0.164(8) 0.466(4) 0.223 Uiso 1 1 d D . . H3W1 H 0.506(10) -0.109(8) 0.235(6) 0.223 Uiso 1 1 d D . . H3W2 H 0.490(12) -0.063(10) 0.3183(17) 0.223 Uiso 1 1 d D . . H4W1 H -0.359(10) -0.182(6) 0.221(9) 0.223 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mo1 0.0403(2) 0.0385(2) 0.0457(2) 0.01788(17) 0.01562(17) 0.00903(17) Mo2 0.0473(2) 0.0423(2) 0.0466(2) 0.01719(18) 0.02178(18) 0.01428(18) N1 0.070(3) 0.041(2) 0.052(2) 0.0166(19) 0.022(2) 0.017(2) N2 0.049(2) 0.063(3) 0.056(2) 0.037(2) 0.0246(19) 0.019(2) N11 0.048(2) 0.053(2) 0.048(2) 0.0208(19) 0.0248(18) 0.0138(19) N12 0.053(2) 0.063(3) 0.045(2) 0.0218(19) 0.0250(18) 0.007(2) O1 0.0514(17) 0.0423(16) 0.0535(19) 0.0191(14) 0.0260(15) 0.0187(14) O2 0.062(2) 0.0555(19) 0.065(2) 0.0305(17) 0.0321(17) 0.0196(17) O3 0.133(4) 0.123(4) 0.105(3) 0.064(3) 0.091(3) 0.051(3) O4 0.122(4) 0.116(4) 0.087(4) 0.039(3) 0.027(3) 0.049(3) O5 0.234(7) 0.126(5) 0.088(4) 0.047(4) 0.065(4) 0.099(5) O6 0.128(4) 0.069(3) 0.094(3) 0.029(3) 0.013(3) 0.010(3) O7 0.165(5) 0.058(3) 0.088(4) 0.010(2) 0.043(3) 0.015(3) O8 0.058(2) 0.063(2) 0.081(3) 0.021(2) 0.0091(19) 0.0088(18) O9 0.0573(18) 0.0397(15) 0.0495(17) 0.0218(13) 0.0278(15) 0.0225(14) O11 0.0515(17) 0.0467(17) 0.0483(17) 0.0229(14) 0.0307(14) 0.0185(14) O12 0.0541(18) 0.0482(18) 0.061(2) 0.0220(16) 0.0357(16) 0.0172(15) O13 0.070(2) 0.074(2) 0.067(2) 0.0410(19) 0.0467(19) 0.0268(19) O14 0.074(3) 0.087(3) 0.121(4) 0.014(3) 0.045(3) 0.025(2) O15 0.057(2) 0.107(4) 0.114(4) 0.024(3) 0.029(2) 0.012(3) O16 0.072(3) 0.069(3) 0.121(4) 0.028(3) 0.015(2) 0.020(2) O17 0.124(4) 0.062(3) 0.145(5) 0.018(3) 0.011(4) -0.019(3) O18 0.0577(19) 0.059(2) 0.057(2) 0.0169(16) 0.0205(16) 0.0140(17) C1 0.072(3) 0.068(3) 0.056(3) 0.026(3) 0.037(3) 0.027(3) C2 0.061(3) 0.076(4) 0.051(3) 0.028(3) 0.026(3) 0.012(3) C3 0.067(4) 0.130(6) 0.103(5) 0.073(4) 0.053(3) 0.054(4) C4 0.091(5) 0.096(5) 0.092(5) 0.039(4) 0.044(4) 0.057(4) C5 0.109(5) 0.076(4) 0.081(4) 0.030(3) 0.054(4) 0.045(4) C6 0.114(5) 0.048(3) 0.041(3) 0.007(2) 0.026(3) 0.020(3) C7 0.104(5) 0.044(3) 0.078(4) 0.012(3) 0.016(4) 0.013(3) C8 0.154(7) 0.048(3) 0.067(4) 0.000(3) 0.023(4) -0.008(4) C9 0.195(9) 0.072(5) 0.087(5) 0.028(4) 0.059(6) 0.072(6) C10 0.110(5) 0.055(3) 0.078(4) 0.019(3) 0.038(4) 0.045(3) C11 0.074(4) 0.069(3) 0.066(3) 0.041(3) 0.046(3) 0.037(3) C12 0.050(3) 0.064(3) 0.048(3) 0.027(2) 0.024(2) 0.014(2) C13 0.053(3) 0.125(6) 0.079(4) 0.060(4) 0.030(3) 0.044(4) C14 0.045(3) 0.140(7) 0.066(4) 0.031(4) 0.006(3) -0.010(4) C15 0.070(4) 0.099(5) 0.082(5) 0.037(4) 0.016(3) -0.005(4) C16 0.049(3) 0.058(3) 0.043(3) 0.004(2) -0.008(2) -0.014(2) C21 0.046(2) 0.046(2) 0.041(2) 0.0193(19) 0.0185(19) 0.013(2) C22 0.050(3) 0.050(3) 0.041(3) 0.010(2) 0.016(2) 0.008(2) C23 0.055(3) 0.065(3) 0.065(3) 0.030(3) 0.021(2) 0.020(3) C24 0.061(3) 0.075(4) 0.066(4) 0.035(3) 0.025(3) 0.024(3) C25 0.075(3) 0.054(3) 0.065(3) 0.032(3) 0.040(3) 0.022(3) C26 0.078(4) 0.049(3) 0.050(3) 0.009(2) 0.009(3) -0.006(3) C27 0.059(3) 0.067(3) 0.065(3) 0.027(3) 0.020(3) 0.019(3) C28 0.076(4) 0.082(4) 0.077(4) 0.032(4) 0.024(3) 0.040(4) C29 0.104(5) 0.081(4) 0.094(5) 0.043(4) 0.042(4) 0.057(4) C30 0.106(5) 0.054(3) 0.072(4) 0.013(3) 0.049(4) 0.024(3) C31 0.073(3) 0.042(3) 0.060(3) 0.019(2) 0.042(3) 0.017(2) C32 0.056(3) 0.048(3) 0.052(3) 0.008(2) 0.030(2) 0.009(2) C33 0.084(4) 0.057(3) 0.080(4) 0.002(3) 0.046(3) 0.009(3) C34 0.064(4) 0.074(4) 0.086(4) 0.006(3) 0.025(3) 0.006(3) C35 0.046(3) 0.097(5) 0.055(3) 0.015(3) 0.004(3) 0.000(3) C36 0.052(3) 0.070(3) 0.082(4) 0.040(3) 0.027(3) 0.016(3) O1W 0.126(4) 0.060(2) 0.102(3) 0.027(3) 0.068(3) 0.024(3) O2W 0.070(3) 0.183(6) 0.135(4) 0.093(5) 0.046(3) 0.045(3) O3W 0.251(9) 0.097(4) 0.186(7) 0.021(5) 0.136(7) 0.034(5) O4W 0.126(5) 0.190(8) 0.174(7) -0.041(6) 0.031(5) -0.012(5) _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 O8 1.676(4) . ? Mo1 O9 1.875(3) . ? Mo1 O1 1.987(3) . ? Mo1 O2 2.075(3) . ? Mo1 N1 2.277(4) . ? Mo1 N2 2.351(4) . ? Mo2 O18 1.686(3) . ? Mo2 O9 1.888(3) . ? Mo2 O11 1.976(3) . ? Mo2 O12 2.077(3) . ? Mo2 N11 2.257(4) . ? Mo2 N12 2.342(4) . ? N1 C7 1.323(7) . ? N1 C11 1.344(6) . ? N2 C16 1.339(6) . ? N2 C12 1.345(6) . ? N11 C27 1.341(6) . ? N11 C31 1.370(6) . ? N12 C36 1.330(6) . ? N12 C32 1.362(6) . ? O1 C1 1.435(6) . ? O2 C2 1.308(6) . ? O3 C2 1.207(6) . ? O4 C4 1.194(8) . ? O5 C4 1.343(9) . ? O6 C6 1.231(7) . ? O7 C6 1.324(8) . ? O11 C21 1.435(5) . ? O12 C22 1.299(6) . ? O13 C22 1.226(5) . ? O14 C24 1.217(7) . ? O15 C24 1.294(7) . ? O16 C26 1.232(7) . ? O17 C26 1.332(7) . ? C1 C5 1.545(8) . ? C1 C3 1.549(8) . ? C1 C2 1.558(7) . ? C3 C4 1.533(9) . ? C5 C6 1.478(9) . ? C7 C8 1.408(9) . ? C8 C9 1.380(10) . ? C9 C10 1.377(10) . ? C10 C11 1.402(7) . ? C11 C12 1.480(7) . ? C12 C13 1.424(7) . ? C13 C14 1.356(9) . ? C14 C15 1.389(10) . ? C15 C16 1.361(8) . ? C21 C25 1.531(6) . ? C21 C23 1.545(6) . ? C21 C22 1.549(6) . ? C23 C24 1.554(7) . ? C25 C26 1.464(7) . ? C27 C28 1.358(8) . ? C28 C29 1.381(9) . ? C29 C30 1.403(9) . ? C30 C31 1.398(7) . ? C31 C32 1.484(7) . ? C32 C33 1.405(7) . ? C33 C34 1.362(9) . ? C34 C35 1.370(8) . ? C35 C36 1.432(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 Mo1 O9 102.77(17) . . ? O8 Mo1 O1 106.66(16) . . ? O9 Mo1 O1 92.12(12) . . ? O8 Mo1 O2 100.68(17) . . ? O9 Mo1 O2 156.36(13) . . ? O1 Mo1 O2 78.25(13) . . ? O8 Mo1 N1 86.72(17) . . ? O9 Mo1 N1 95.32(14) . . ? O1 Mo1 N1 162.87(14) . . ? O2 Mo1 N1 88.95(14) . . ? O8 Mo1 N2 156.48(17) . . ? O9 Mo1 N2 79.23(13) . . ? O1 Mo1 N2 96.62(14) . . ? O2 Mo1 N2 80.50(13) . . ? N1 Mo1 N2 69.78(15) . . ? O18 Mo2 O9 102.00(15) . . ? O18 Mo2 O11 110.11(15) . . ? O9 Mo2 O11 92.25(12) . . ? O18 Mo2 O12 100.75(15) . . ? O9 Mo2 O12 157.18(13) . . ? O11 Mo2 O12 78.28(12) . . ? O18 Mo2 N11 87.05(16) . . ? O9 Mo2 N11 93.03(12) . . ? O11 Mo2 N11 160.55(13) . . ? O12 Mo2 N11 89.83(13) . . ? O18 Mo2 N12 157.34(16) . . ? O9 Mo2 N12 79.64(13) . . ? O11 Mo2 N12 92.32(14) . . ? O12 Mo2 N12 80.05(13) . . ? N11 Mo2 N12 70.29(14) . . ? C7 N1 C11 118.7(5) . . ? C7 N1 Mo1 120.7(4) . . ? C11 N1 Mo1 120.5(3) . . ? C16 N2 C12 120.4(4) . . ? C16 N2 Mo1 121.1(3) . . ? C12 N2 Mo1 118.1(3) . . ? C27 N11 C31 118.0(4) . . ? C27 N11 Mo2 121.3(3) . . ? C31 N11 Mo2 120.7(3) . . ? C36 N12 C32 118.9(5) . . ? C36 N12 Mo2 122.6(4) . . ? C32 N12 Mo2 118.5(3) . . ? C1 O1 Mo1 115.5(3) . . ? C2 O2 Mo1 117.5(3) . . ? Mo1 O9 Mo2 169.92(17) . . ? C21 O11 Mo2 119.2(2) . . ? C22 O12 Mo2 117.0(3) . . ? O1 C1 C5 109.3(4) . . ? O1 C1 C3 109.8(4) . . ? C5 C1 C3 111.6(5) . . ? O1 C1 C2 109.6(4) . . ? C5 C1 C2 112.2(4) . . ? C3 C1 C2 104.3(4) . . ? O2 C2 O3 124.9(5) . . ? O2 C2 C1 113.0(4) . . ? O3 C2 C1 122.1(5) . . ? C4 C3 C1 115.0(5) . . ? O4 C4 O5 126.1(7) . . ? O4 C4 C3 122.4(7) . . ? O5 C4 C3 111.4(7) . . ? C6 C5 C1 110.7(5) . . ? O6 C6 O7 119.3(6) . . ? O6 C6 C5 125.8(6) . . ? O7 C6 C5 114.8(6) . . ? N1 C7 C8 123.8(6) . . ? C9 C8 C7 115.9(6) . . ? C10 C9 C8 121.9(6) . . ? C9 C10 C11 117.4(6) . . ? N1 C11 C10 122.1(6) . . ? N1 C11 C12 115.9(4) . . ? C10 C11 C12 122.0(5) . . ? N2 C12 C13 120.4(5) . . ? N2 C12 C11 115.5(4) . . ? C13 C12 C11 124.0(5) . . ? C14 C13 C12 118.0(6) . . ? C13 C14 C15 120.2(5) . . ? C16 C15 C14 119.7(6) . . ? N2 C16 C15 121.1(6) . . ? O11 C21 C25 111.9(4) . . ? O11 C21 C23 109.2(4) . . ? C25 C21 C23 110.7(4) . . ? O11 C21 C22 108.2(4) . . ? C25 C21 C22 111.4(4) . . ? C23 C21 C22 105.2(4) . . ? O12 C22 O13 122.5(4) . . ? O12 C22 C21 115.2(4) . . ? O13 C22 C21 122.2(4) . . ? C21 C23 C24 111.9(4) . . ? O14 C24 O15 123.8(5) . . ? O14 C24 C23 122.3(5) . . ? O15 C24 C23 113.6(5) . . ? C26 C25 C21 117.8(4) . . ? O16 C26 O17 121.2(5) . . ? O16 C26 C25 127.0(5) . . ? O17 C26 C25 111.8(5) . . ? N11 C27 C28 124.5(5) . . ? C27 C28 C29 119.0(5) . . ? C28 C29 C30 118.4(5) . . ? C31 C30 C29 119.8(6) . . ? N11 C31 C30 120.4(5) . . ? N11 C31 C32 115.7(4) . . ? C30 C31 C32 123.9(5) . . ? N12 C32 C33 121.3(5) . . ? N12 C32 C31 114.7(4) . . ? C33 C32 C31 124.0(5) . . ? C34 C33 C32 119.7(5) . . ? C33 C34 C35 119.6(6) . . ? C34 C35 C36 118.9(5) . . ? N12 C36 C35 121.4(5) . . ? _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 32.50 _diffrn_measured_fraction_theta_full 0.874 _refine_diff_density_max 1.558 _refine_diff_density_min -0.646 _refine_diff_density_rms 0.116 # Attachment 'cif3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 673572' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Monomeric bipyridine citrato dioxomolybdenum complex' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 Mo N2 O10' _chemical_formula_weight 492.25 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' 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 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.688(1) _cell_length_b 7.7377(8) _cell_length_c 16.084(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.151(2) _cell_angle_gamma 90.00 _cell_volume 1799.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.817 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.791 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.9322 _exptl_absorpt_correction_T_max 0.9690 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10660 _diffrn_reflns_av_R_equivalents 0.1278 _diffrn_reflns_av_sigmaI/netI 0.1341 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3167 _reflns_number_gt 2091 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0658P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3167 _refine_ls_number_parameters 274 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1350 _refine_ls_R_factor_gt 0.0851 _refine_ls_wR_factor_ref 0.1803 _refine_ls_wR_factor_gt 0.1588 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.037 _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 Mo1 Mo 1.09502(6) 0.31160(11) 0.72024(5) 0.0342(3) Uani 1 1 d . . . N1 N 1.1656(6) 0.2407(10) 0.6161(5) 0.041(2) Uani 1 1 d . . . N2 N 0.9933(5) 0.3099(10) 0.5971(5) 0.0381(19) Uani 1 1 d . . . O1 O 1.0015(4) 0.2874(7) 0.7880(4) 0.0366(16) Uani 1 1 d . . . O2 O 1.0544(4) 0.0456(8) 0.7054(4) 0.0434(17) Uani 1 1 d . . . O3 O 0.9916(7) -0.1608(10) 0.7658(6) 0.087(3) Uani 1 1 d . . . O4 O 0.9781(7) 0.3076(14) 0.9752(6) 0.102(4) Uani 1 1 d . . . O5 O 1.1199(6) 0.2474(12) 1.0252(5) 0.073(3) Uani 1 1 d D . . O6 O 0.8286(5) 0.0841(11) 0.6890(5) 0.069(2) Uani 1 1 d . . . O7 O 0.7360(6) 0.0829(14) 0.7829(5) 0.082(3) Uani 1 1 d D . . O8 O 1.1943(5) 0.2727(10) 0.7859(4) 0.056(2) Uani 1 1 d . . . O9 O 1.0901(5) 0.5263(8) 0.7119(4) 0.0479(18) Uani 1 1 d . . . C1 C 0.9885(7) 0.1229(13) 0.8212(6) 0.039(2) Uani 1 1 d . . . C2 C 1.0120(8) -0.0116(14) 0.7605(7) 0.052(3) Uani 1 1 d . . . C3 C 1.0552(7) 0.1004(14) 0.9039(6) 0.048(3) Uani 1 1 d . . . H3A H 1.0464 -0.0138 0.9260 0.058 Uiso 1 1 calc R . . H3B H 1.1179 0.1063 0.8927 0.058 Uiso 1 1 calc R . . C4 C 1.0446(9) 0.2320(14) 0.9702(7) 0.050(3) Uani 1 1 d . . . C5 C 0.8898(7) 0.1017(13) 0.8359(6) 0.047(3) Uani 1 1 d . . . H5A H 0.8871 -0.0015 0.8696 0.056 Uiso 1 1 calc R . . H5B H 0.8753 0.1991 0.8692 0.056 Uiso 1 1 calc R . . C6 C 0.8175(8) 0.0888(14) 0.7606(8) 0.053(3) Uani 1 1 d . . . C7 C 1.2565(7) 0.2104(14) 0.6310(7) 0.056(3) Uani 1 1 d . . . H7A H 1.2903 0.2317 0.6846 0.067 Uiso 1 1 calc R . . C8 C 1.3011(9) 0.1486(15) 0.5692(8) 0.065(4) Uani 1 1 d . . . H8A H 1.3640 0.1235 0.5810 0.078 Uiso 1 1 calc R . . C9 C 1.2525(10) 0.1251(15) 0.4916(9) 0.069(4) Uani 1 1 d . . . H9A H 1.2828 0.0887 0.4486 0.082 Uiso 1 1 calc R . . C10 C 1.1598(10) 0.1534(12) 0.4743(7) 0.059(3) Uani 1 1 d . . . H10A H 1.1257 0.1312 0.4210 0.070 Uiso 1 1 calc R . . C11 C 1.1178(8) 0.2165(10) 0.5388(6) 0.039(2) Uani 1 1 d . . . C12 C 1.0191(7) 0.2569(11) 0.5277(6) 0.038(2) Uani 1 1 d . . . C13 C 0.9587(9) 0.2441(13) 0.4527(6) 0.055(3) Uani 1 1 d . . . H13A H 0.9788 0.2041 0.4045 0.065 Uiso 1 1 calc R . . C14 C 0.8698(9) 0.2900(17) 0.4495(8) 0.072(4) Uani 1 1 d . . . H14A H 0.8280 0.2828 0.3990 0.086 Uiso 1 1 calc R . . C15 C 0.8417(8) 0.3468(15) 0.5206(8) 0.062(3) Uani 1 1 d . . . H15A H 0.7803 0.3768 0.5202 0.075 Uiso 1 1 calc R . . C16 C 0.9058(7) 0.3585(13) 0.5926(7) 0.049(3) Uani 1 1 d . . . H16A H 0.8875 0.4027 0.6408 0.059 Uiso 1 1 calc R . . O1W O 0.9133(5) -0.4089(9) 0.8367(5) 0.0514(19) Uani 1 1 d D . . H1 H 1.108(8) 0.299(12) 1.069(4) 0.062 Uiso 1 1 d D . . H2 H 0.702(6) 0.064(14) 0.735(3) 0.062 Uiso 1 1 d D . . H1W1 H 0.943(5) -0.503(5) 0.841(6) 0.062 Uiso 1 1 d D . . H1W2 H 0.944(5) -0.329(7) 0.819(6) 0.062 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mo1 0.0359(5) 0.0418(5) 0.0258(5) -0.0003(5) 0.0078(3) -0.0011(5) N1 0.041(5) 0.053(5) 0.031(5) 0.006(4) 0.010(4) 0.004(4) N2 0.042(5) 0.043(5) 0.031(5) 0.008(4) 0.012(4) 0.003(4) O1 0.048(4) 0.034(4) 0.032(4) 0.006(3) 0.017(3) 0.007(3) O2 0.042(4) 0.035(4) 0.054(4) -0.008(3) 0.014(3) -0.007(3) O3 0.127(8) 0.044(5) 0.110(7) -0.003(5) 0.078(6) -0.016(5) O4 0.067(7) 0.159(10) 0.074(6) -0.058(6) -0.005(5) 0.022(7) O5 0.047(5) 0.096(7) 0.070(6) -0.011(5) -0.006(5) 0.006(5) O6 0.073(6) 0.103(7) 0.036(5) -0.007(5) 0.019(4) -0.018(5) O7 0.047(6) 0.144(9) 0.056(6) 0.010(6) 0.010(4) -0.007(6) O8 0.043(5) 0.090(6) 0.035(4) 0.006(4) 0.010(3) -0.001(4) O9 0.064(5) 0.047(4) 0.032(4) -0.009(3) 0.007(3) -0.010(4) C1 0.036(6) 0.053(6) 0.032(6) -0.003(5) 0.014(5) -0.004(5) C2 0.071(8) 0.037(6) 0.052(7) 0.017(6) 0.021(6) -0.004(6) C3 0.036(6) 0.055(7) 0.056(7) 0.013(6) 0.015(5) 0.009(5) C4 0.054(8) 0.058(8) 0.044(7) 0.020(6) 0.023(6) 0.006(6) C5 0.053(7) 0.046(6) 0.044(6) -0.005(5) 0.011(6) 0.008(5) C6 0.050(8) 0.049(7) 0.061(8) 0.002(6) 0.014(7) -0.018(6) C7 0.034(6) 0.078(8) 0.060(7) 0.006(7) 0.018(6) -0.003(6) C8 0.052(8) 0.071(9) 0.078(9) 0.019(7) 0.034(7) 0.024(6) C9 0.078(10) 0.067(9) 0.073(10) 0.008(7) 0.047(8) 0.010(7) C10 0.095(10) 0.037(7) 0.052(7) -0.007(5) 0.036(7) -0.004(7) C11 0.065(7) 0.014(5) 0.040(6) 0.003(4) 0.019(6) -0.002(5) C12 0.052(7) 0.029(5) 0.032(6) -0.001(4) 0.003(5) -0.002(5) C13 0.088(10) 0.043(6) 0.032(7) 0.007(5) 0.012(7) -0.015(6) C14 0.052(8) 0.092(10) 0.064(9) 0.017(8) -0.010(7) -0.025(8) C15 0.038(7) 0.077(9) 0.070(9) 0.021(7) 0.003(7) -0.004(6) C16 0.045(7) 0.052(7) 0.047(7) 0.007(5) 0.001(6) 0.002(5) O1W 0.058(5) 0.043(4) 0.053(5) 0.008(4) 0.008(4) -0.005(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mo1 O9 1.667(6) . ? Mo1 O8 1.670(6) . ? Mo1 O1 1.907(6) . ? Mo1 O2 2.144(6) . ? Mo1 N1 2.189(8) . ? Mo1 N2 2.261(7) . ? N1 C11 1.329(12) . ? N1 C7 1.334(12) . ? N2 C12 1.307(11) . ? N2 C16 1.329(12) . ? O1 C1 1.406(11) . ? O2 C2 1.250(11) . ? O3 C2 1.200(11) . ? O4 C4 1.153(12) . ? O5 C4 1.293(13) . ? O6 C6 1.192(12) . ? O7 C6 1.310(13) . ? C1 C2 1.509(14) . ? C1 C3 1.516(13) . ? C1 C5 1.518(13) . ? C3 C4 1.503(14) . ? C5 C6 1.467(13) . ? C7 C8 1.370(15) . ? C8 C9 1.336(16) . ? C9 C10 1.358(16) . ? C10 C11 1.386(14) . ? C11 C12 1.463(14) . ? C12 C13 1.369(13) . ? C13 C14 1.345(15) . ? C14 C15 1.356(16) . ? C15 C16 1.360(14) . ? 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 O9 Mo1 O8 104.5(4) . . ? O9 Mo1 O1 96.8(3) . . ? O8 Mo1 O1 105.0(3) . . ? O9 Mo1 O2 160.1(3) . . ? O8 Mo1 O2 95.3(3) . . ? O1 Mo1 O2 75.8(3) . . ? O9 Mo1 N1 102.0(3) . . ? O8 Mo1 N1 87.7(3) . . ? O1 Mo1 N1 153.9(3) . . ? O2 Mo1 N1 80.5(3) . . ? O9 Mo1 N2 85.6(3) . . ? O8 Mo1 N2 157.1(3) . . ? O1 Mo1 N2 93.9(3) . . ? O2 Mo1 N2 76.7(3) . . ? N1 Mo1 N2 70.0(3) . . ? C11 N1 C7 119.3(9) . . ? C11 N1 Mo1 120.5(7) . . ? C7 N1 Mo1 120.0(7) . . ? C12 N2 C16 117.7(9) . . ? C12 N2 Mo1 120.3(7) . . ? C16 N2 Mo1 122.0(7) . . ? C1 O1 Mo1 117.8(5) . . ? C2 O2 Mo1 115.1(7) . . ? O1 C1 C2 108.4(8) . . ? O1 C1 C3 109.1(8) . . ? C2 C1 C3 107.6(9) . . ? O1 C1 C5 110.8(8) . . ? C2 C1 C5 111.1(9) . . ? C3 C1 C5 109.8(8) . . ? O3 C2 O2 123.6(11) . . ? O3 C2 C1 121.9(10) . . ? O2 C2 C1 114.5(9) . . ? C4 C3 C1 114.4(9) . . ? O4 C4 O5 122.6(12) . . ? O4 C4 C3 126.0(12) . . ? O5 C4 C3 111.4(10) . . ? C6 C5 C1 116.8(9) . . ? O6 C6 O7 123.5(11) . . ? O6 C6 C5 126.7(11) . . ? O7 C6 C5 109.8(10) . . ? N1 C7 C8 121.5(11) . . ? C9 C8 C7 118.7(11) . . ? C8 C9 C10 121.4(12) . . ? C9 C10 C11 117.8(12) . . ? N1 C11 C10 121.2(11) . . ? N1 C11 C12 115.7(9) . . ? C10 C11 C12 123.1(10) . . ? N2 C12 C13 122.3(10) . . ? N2 C12 C11 113.1(9) . . ? C13 C12 C11 124.6(10) . . ? C14 C13 C12 119.2(11) . . ? C13 C14 C15 119.5(12) . . ? C14 C15 C16 118.1(12) . . ? N2 C16 C15 123.1(11) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.042 _refine_diff_density_min -0.963 _refine_diff_density_rms 0.127