# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'D Miguel' _publ_contact_author_email DMSJ@QI.UVA.ES _publ_section_title ; Unexpected Chemoselectivity in the Schiff Condensation of Amines with eta-2-(C,O)-?eta-1-(O)-Coordinated Aldehyde ; loop_ _publ_author_name 'D Miguel' 'Celedonio M. Alvarez' 'Raul Garcia-Rodriguez' 'Jose Martin-Alvarez' # Attachment 'B914740C_ccdc_734485_734487_cif.txt' data_Compound_2a_(rg375am) _database_code_depnum_ccdc_archive 'CCDC 734485' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H10 Cr2 N2 O8' _chemical_formula_weight 486.28 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' Cr Cr 0.3209 0.6236 '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 8.1061(19) _cell_length_b 9.046(2) _cell_length_c 12.615(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.182(5) _cell_angle_gamma 90.00 _cell_volume 924.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 563 _cell_measurement_theta_min 2.514 _cell_measurement_theta_max 23.903 _exptl_crystal_description PRISM _exptl_crystal_colour BLACK _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.747 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 1.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.606392 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4978 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0699 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 25.36 _reflns_number_total 1698 _reflns_number_gt 1174 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0445P)^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 1698 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _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 Cr1 Cr 0.05941(7) 1.08597(6) 0.11017(4) 0.0294(2) Uani 1 1 d . . . N1 N 0.2631(3) 0.9438(3) 0.0927(2) 0.0308(7) Uani 1 1 d . . . C1 C -0.1351(5) 1.1585(4) 0.1634(3) 0.0370(10) Uani 1 1 d . . . O1 O -0.2539(4) 1.2018(3) 0.1995(2) 0.0541(8) Uani 1 1 d . . . C2 C 0.1753(5) 1.2560(5) 0.1392(3) 0.0397(10) Uani 1 1 d . . . O2 O 0.2455(4) 1.3648(3) 0.1563(3) 0.0658(10) Uani 1 1 d . . . C3 C 0.1011(5) 1.0470(4) 0.2559(3) 0.0370(10) Uani 1 1 d . . . O3 O 0.1308(4) 1.0308(3) 0.3440(2) 0.0564(9) Uani 1 1 d . . . O4 O -0.0566(3) 0.8894(3) 0.05243(17) 0.0298(6) Uani 1 1 d . . . C4 C 0.0506(5) 0.7887(4) 0.0210(3) 0.0336(9) Uani 1 1 d . . . H4 H 0.0122 0.6863 0.0256 0.040 Uiso 1 1 calc R . . C11 C 0.4213(5) 0.9688(5) 0.1244(3) 0.0418(10) Uani 1 1 d . . . H11 H 0.4486 1.0603 0.1537 0.050 Uiso 1 1 calc R . . C12 C 0.5426(5) 0.8664(5) 0.1157(3) 0.0493(12) Uani 1 1 d . . . H12 H 0.6504 0.8878 0.1385 0.059 Uiso 1 1 calc R . . C13 C 0.5037(6) 0.7307(6) 0.0725(4) 0.0554(13) Uani 1 1 d . . . H13 H 0.5851 0.6592 0.0656 0.066 Uiso 1 1 calc R . . C14 C 0.3437(5) 0.7017(5) 0.0399(3) 0.0455(11) Uani 1 1 d . . . H14 H 0.3151 0.6106 0.0103 0.055 Uiso 1 1 calc R . . C15 C 0.2250(5) 0.8105(4) 0.0517(3) 0.0324(9) 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 Cr1 0.0275(4) 0.0341(4) 0.0266(3) -0.0026(3) 0.0006(2) -0.0003(3) N1 0.0218(18) 0.043(2) 0.0275(16) 0.0008(14) 0.0022(14) 0.0038(14) C1 0.042(3) 0.042(2) 0.027(2) 0.0023(18) -0.003(2) -0.004(2) O1 0.042(2) 0.074(2) 0.0472(18) -0.0068(15) 0.0135(16) 0.0130(17) C2 0.038(3) 0.047(3) 0.034(2) -0.0034(19) -0.0031(19) -0.002(2) O2 0.070(2) 0.057(2) 0.069(2) -0.0069(17) -0.0107(18) -0.0240(18) C3 0.029(2) 0.043(2) 0.039(2) -0.0044(18) 0.0045(19) 0.0063(18) O3 0.068(2) 0.069(2) 0.0320(16) 0.0002(14) -0.0063(15) 0.0139(16) O4 0.0256(14) 0.0369(15) 0.0271(13) -0.0013(11) 0.0040(11) -0.0018(12) C4 0.039(3) 0.035(2) 0.027(2) 0.0019(16) 0.0045(18) -0.0013(18) C11 0.028(2) 0.059(3) 0.038(2) 0.006(2) 0.0016(19) -0.004(2) C12 0.025(2) 0.082(3) 0.041(2) 0.015(2) -0.001(2) 0.006(2) C13 0.041(3) 0.076(4) 0.049(3) 0.006(2) 0.004(2) 0.032(2) C14 0.049(3) 0.049(3) 0.038(2) 0.0005(19) -0.003(2) 0.018(2) C15 0.037(2) 0.039(2) 0.0212(18) 0.0046(16) 0.0032(17) 0.0054(18) _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 Cr1 C2 1.832(4) . ? Cr1 C1 1.857(5) . ? Cr1 C3 1.889(4) . ? Cr1 O4 2.063(2) 3_575 ? Cr1 N1 2.111(3) . ? Cr1 O4 2.127(2) . ? Cr1 C4 2.170(4) 3_575 ? N1 C15 1.343(4) . ? N1 C11 1.348(5) . ? C1 O1 1.149(4) . ? C2 O2 1.153(4) . ? C3 O3 1.138(4) . ? O4 C4 1.330(4) . ? O4 Cr1 2.063(2) 3_575 ? C4 C15 1.465(5) . ? C4 Cr1 2.169(3) 3_575 ? C11 C12 1.359(6) . ? C12 C13 1.375(6) . ? C13 C14 1.371(6) . ? C14 C15 1.389(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 C2 Cr1 C1 93.84(18) . . ? C2 Cr1 C3 83.74(17) . . ? C1 Cr1 C3 80.60(16) . . ? C2 Cr1 O4 95.40(14) . 3_575 ? C1 Cr1 O4 110.15(13) . 3_575 ? C3 Cr1 O4 169.26(14) . 3_575 ? C2 Cr1 N1 97.78(15) . . ? C1 Cr1 N1 158.62(14) . . ? C3 Cr1 N1 82.90(14) . . ? O4 Cr1 N1 86.62(10) 3_575 . ? C2 Cr1 O4 170.73(15) . . ? C1 Cr1 O4 92.81(13) . . ? C3 Cr1 O4 103.74(13) . . ? O4 Cr1 O4 76.22(10) 3_575 . ? N1 Cr1 O4 78.01(10) . . ? C2 Cr1 C4 84.63(16) . 3_575 ? C1 Cr1 C4 76.19(15) . 3_575 ? C3 Cr1 C4 153.21(16) . 3_575 ? O4 Cr1 C4 36.52(11) 3_575 3_575 ? N1 Cr1 C4 122.63(13) . 3_575 ? O4 Cr1 C4 90.69(12) . 3_575 ? C15 N1 C11 117.9(3) . . ? C15 N1 Cr1 114.7(2) . . ? C11 N1 Cr1 127.3(3) . . ? O1 C1 Cr1 177.9(3) . . ? O2 C2 Cr1 178.5(4) . . ? O3 C3 Cr1 176.2(4) . . ? C4 O4 Cr1 76.12(18) . 3_575 ? C4 O4 Cr1 112.9(2) . . ? Cr1 O4 Cr1 103.78(10) 3_575 . ? O4 C4 C15 117.7(3) . . ? O4 C4 Cr1 67.37(18) . 3_575 ? C15 C4 Cr1 119.7(3) . 3_575 ? N1 C11 C12 123.0(4) . . ? C11 C12 C13 119.0(4) . . ? C14 C13 C12 119.3(4) . . ? C13 C14 C15 118.9(4) . . ? N1 C15 C14 121.8(4) . . ? N1 C15 C4 115.4(3) . . ? C14 C15 C4 122.8(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.472 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.076 #===END data_Compound_2b_(rg312bm) _database_code_depnum_ccdc_archive 'CCDC 734486' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H10 Mo2 N2 O8' _chemical_formula_weight 574.16 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 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 8.151(4) _cell_length_b 9.078(5) _cell_length_c 12.908(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.576(10) _cell_angle_gamma 90.00 _cell_volume 954.1(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3.666 _cell_measurement_theta_max 25.347 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.999 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 1.365 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.866322 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5074 _diffrn_reflns_av_R_equivalents 0.0146 _diffrn_reflns_av_sigmaI/netI 0.0123 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 25.41 _reflns_number_total 1742 _reflns_number_gt 1636 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0255P)^2^+0.3922P] 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 1742 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0183 _refine_ls_R_factor_gt 0.0169 _refine_ls_wR_factor_ref 0.0451 _refine_ls_wR_factor_gt 0.0443 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mo1 Mo 0.940700(18) 1.090700(18) 0.885498(11) 0.02813(8) Uani 1 1 d . . . N1 N 0.72859(19) 0.94074(19) 0.90790(12) 0.0320(4) Uani 1 1 d . . . C1 C 1.1465(2) 1.1653(2) 0.82779(15) 0.0368(4) Uani 1 1 d . . . O1 O 1.26491(19) 1.2067(2) 0.79305(13) 0.0534(4) Uani 1 1 d . . . C2 C 0.8260(3) 1.2741(3) 0.85599(16) 0.0397(5) Uani 1 1 d . . . O2 O 0.7570(2) 1.3836(2) 0.84220(16) 0.0650(5) Uani 1 1 d . . . C3 C 0.8929(2) 1.0531(2) 0.73389(16) 0.0365(4) Uani 1 1 d . . . O3 O 0.8599(2) 1.0385(2) 0.64710(12) 0.0539(4) Uani 1 1 d . . . O4 O 1.04979(16) 0.88009(15) 0.94814(10) 0.0303(3) Uani 1 1 d . . . C4 C 0.9390(2) 0.7832(2) 0.98185(14) 0.0318(4) Uani 1 1 d . . . H4 H 0.9727 0.6798 0.9778 0.038 Uiso 1 1 calc R . . C11 C 0.5716(2) 0.9670(3) 0.87585(16) 0.0407(5) Uani 1 1 d . . . H11 H 0.5458 1.0567 0.8443 0.049 Uiso 1 1 calc R . . C12 C 0.4484(2) 0.8660(3) 0.88820(17) 0.0491(6) Uani 1 1 d . . . H12 H 0.3414 0.8868 0.8648 0.059 Uiso 1 1 calc R . . C13 C 0.4851(3) 0.7350(3) 0.93519(18) 0.0534(6) Uani 1 1 d . . . H13 H 0.4027 0.6663 0.9455 0.064 Uiso 1 1 calc R . . C14 C 0.6450(3) 0.7048(3) 0.96731(17) 0.0453(5) Uani 1 1 d . . . H14 H 0.6721 0.6152 0.9985 0.054 Uiso 1 1 calc R . . C15 C 0.7648(2) 0.8102(2) 0.95245(14) 0.0326(4) 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 Mo1 0.02637(11) 0.03106(12) 0.02704(11) 0.00333(6) 0.00202(7) 0.00025(6) N1 0.0268(8) 0.0390(9) 0.0301(8) -0.0022(7) 0.0023(6) -0.0012(7) C1 0.0401(11) 0.0398(12) 0.0305(10) 0.0028(9) 0.0011(8) -0.0008(9) O1 0.0438(9) 0.0684(12) 0.0492(9) 0.0074(8) 0.0155(7) -0.0125(8) C2 0.0397(11) 0.0428(12) 0.0364(11) 0.0041(9) 0.0003(8) 0.0024(10) O2 0.0735(13) 0.0505(11) 0.0704(12) 0.0098(9) -0.0034(10) 0.0246(10) C3 0.0355(10) 0.0384(11) 0.0357(11) 0.0055(9) 0.0026(8) -0.0021(9) O3 0.0649(11) 0.0646(11) 0.0315(8) 0.0008(8) -0.0046(7) -0.0058(9) O4 0.0277(6) 0.0341(7) 0.0292(7) 0.0012(5) 0.0042(5) 0.0016(5) C4 0.0360(10) 0.0291(10) 0.0306(9) -0.0009(8) 0.0031(8) 0.0004(8) C11 0.0303(10) 0.0544(14) 0.0373(11) -0.0044(10) 0.0002(8) 0.0013(10) C12 0.0287(11) 0.0738(18) 0.0447(13) -0.0086(11) -0.0003(10) -0.0078(10) C13 0.0419(12) 0.0691(17) 0.0491(13) -0.0044(12) 0.0013(10) -0.0256(12) C14 0.0495(12) 0.0438(13) 0.0422(12) 0.0007(10) -0.0011(9) -0.0157(10) C15 0.0338(10) 0.0377(11) 0.0264(9) -0.0046(8) 0.0029(7) -0.0047(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mo1 C2 1.939(2) . ? Mo1 C1 1.985(2) . ? Mo1 C3 2.007(2) . ? Mo1 O4 2.1617(17) 3_777 ? Mo1 N1 2.2295(19) . ? Mo1 O4 2.2438(16) . ? Mo1 C4 2.248(2) 3_777 ? N1 C15 1.344(3) . ? N1 C11 1.348(3) . ? C1 O1 1.146(2) . ? C2 O2 1.152(3) . ? C3 O3 1.148(3) . ? O4 C4 1.347(2) . ? O4 Mo1 2.1617(17) 3_777 ? C4 C15 1.473(3) . ? C4 Mo1 2.248(2) 3_777 ? C11 C12 1.375(3) . ? C12 C13 1.362(4) . ? C13 C14 1.377(3) . ? C14 C15 1.387(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 C2 Mo1 C1 92.37(9) . . ? C2 Mo1 C3 83.34(9) . . ? C1 Mo1 C3 79.77(8) . . ? C2 Mo1 O4 94.89(7) . 3_777 ? C1 Mo1 O4 109.75(7) . 3_777 ? C3 Mo1 O4 170.42(7) . 3_777 ? C2 Mo1 N1 100.36(9) . . ? C1 Mo1 N1 158.50(8) . . ? C3 Mo1 N1 84.54(7) . . ? O4 Mo1 N1 86.53(6) 3_777 . ? C2 Mo1 O4 169.18(7) . . ? C1 Mo1 O4 95.64(8) . . ? C3 Mo1 O4 105.23(8) . . ? O4 Mo1 O4 75.56(6) 3_777 . ? N1 Mo1 O4 74.34(7) . . ? C2 Mo1 C4 84.40(9) . 3_777 ? C1 Mo1 C4 76.41(8) . 3_777 ? C3 Mo1 C4 152.65(8) . 3_777 ? O4 Mo1 C4 35.49(6) 3_777 3_777 ? N1 Mo1 C4 121.76(7) . 3_777 ? O4 Mo1 C4 90.40(7) . 3_777 ? C15 N1 C11 118.33(18) . . ? C15 N1 Mo1 115.91(12) . . ? C11 N1 Mo1 125.65(15) . . ? O1 C1 Mo1 178.78(19) . . ? O2 C2 Mo1 177.6(2) . . ? O3 C3 Mo1 176.1(2) . . ? C4 O4 Mo1 75.74(10) . 3_777 ? C4 O4 Mo1 114.34(12) . . ? Mo1 O4 Mo1 104.44(6) 3_777 . ? O4 C4 C15 117.43(17) . . ? O4 C4 Mo1 68.76(10) . 3_777 ? C15 C4 Mo1 119.60(13) . 3_777 ? N1 C11 C12 122.3(2) . . ? C13 C12 C11 119.2(2) . . ? C12 C13 C14 119.6(2) . . ? C13 C14 C15 119.0(2) . . ? N1 C15 C14 121.64(19) . . ? N1 C15 C4 116.57(17) . . ? C14 C15 C4 121.8(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.41 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.293 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.052 #===END data_Compound_2c_(rg513dm) _database_code_depnum_ccdc_archive 'CCDC 734487' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H10 N2 O8 W2' _chemical_formula_weight 749.98 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' W W -0.8490 6.8722 '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 8.115(7) _cell_length_b 9.031(8) _cell_length_c 12.919(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.035(18) _cell_angle_gamma 90.00 _cell_volume 946.2(14) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 584 _cell_measurement_theta_min 2.512 _cell_measurement_theta_max 21.658 _exptl_crystal_description PLATE _exptl_crystal_colour BLACK _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 12.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.624551 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7382 _diffrn_reflns_av_R_equivalents 0.0954 _diffrn_reflns_av_sigmaI/netI 0.0915 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 25.40 _reflns_number_total 1731 _reflns_number_gt 1114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0296P)^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 1731 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0870 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 W1 W 0.94090(7) 1.08903(6) 0.88516(4) 0.02677(18) Uani 1 1 d . . . N1 N 0.7322(13) 0.9368(11) 0.9086(7) 0.030(3) Uani 1 1 d . . . C1 C 1.1456(19) 1.1573(15) 0.8252(10) 0.035(3) Uani 1 1 d . . . O1 O 1.2680(13) 1.1972(10) 0.7902(7) 0.049(3) Uani 1 1 d . . . C2 C 0.8226(19) 1.2727(18) 0.8551(9) 0.041(4) Uani 1 1 d . . . O2 O 0.7510(14) 1.3829(12) 0.8422(9) 0.066(3) Uani 1 1 d . . . C3 C 0.8924(18) 1.0551(15) 0.7344(11) 0.040(4) Uani 1 1 d . . . O3 O 0.8561(13) 1.0406(10) 0.6484(7) 0.049(3) Uani 1 1 d . . . O4 O 1.0523(10) 0.8821(9) 0.9492(6) 0.026(2) Uani 1 1 d . . . C4 C 0.9405(15) 0.7819(14) 0.9860(9) 0.027(3) Uani 1 1 d . . . H4 H 0.9762 0.6785 0.9827 0.032 Uiso 1 1 calc R . . C11 C 0.5761(18) 0.9604(16) 0.8748(10) 0.038(4) Uani 1 1 d . . . H11 H 0.5510 1.0485 0.8404 0.045 Uiso 1 1 calc R . . C12 C 0.454(2) 0.8611(18) 0.8888(11) 0.050(4) Uani 1 1 d . . . H12 H 0.3473 0.8814 0.8639 0.060 Uiso 1 1 calc R . . C13 C 0.4871(19) 0.7312(18) 0.9394(11) 0.045(4) Uani 1 1 d . . . H13 H 0.4038 0.6641 0.9531 0.054 Uiso 1 1 calc R . . C14 C 0.6472(19) 0.7035(17) 0.9693(10) 0.045(4) Uani 1 1 d . . . H14 H 0.6747 0.6134 1.0002 0.054 Uiso 1 1 calc R . . C15 C 0.7673(16) 0.8060(14) 0.9544(9) 0.029(3) 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 W1 0.0269(3) 0.0293(3) 0.0240(3) 0.0035(3) 0.00014(19) 0.0004(3) N1 0.028(7) 0.036(7) 0.027(6) -0.001(5) 0.000(5) 0.000(5) C1 0.044(10) 0.034(8) 0.028(8) -0.009(6) -0.003(7) 0.000(7) O1 0.046(7) 0.045(6) 0.058(7) 0.010(5) 0.024(6) -0.007(5) C2 0.049(10) 0.057(10) 0.016(7) 0.004(7) -0.001(7) -0.021(9) O2 0.059(8) 0.057(8) 0.082(8) 0.022(7) -0.013(6) 0.021(7) C3 0.042(9) 0.040(10) 0.039(8) 0.013(7) 0.006(7) 0.008(7) O3 0.068(8) 0.051(7) 0.029(5) -0.001(5) -0.006(5) -0.016(6) O4 0.020(5) 0.036(6) 0.022(4) 0.003(4) -0.001(4) 0.004(4) C4 0.025(8) 0.024(7) 0.033(7) 0.001(6) 0.012(6) -0.005(6) C11 0.029(9) 0.052(10) 0.032(8) -0.006(6) 0.002(6) -0.003(7) C12 0.029(9) 0.087(12) 0.033(8) -0.015(9) -0.005(7) -0.003(10) C13 0.039(10) 0.057(10) 0.040(9) -0.003(8) 0.004(7) -0.024(9) C14 0.046(10) 0.047(10) 0.040(9) -0.003(7) -0.009(8) -0.007(8) C15 0.025(8) 0.034(8) 0.026(7) 0.012(6) -0.001(6) -0.001(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 W1 C2 1.949(17) . ? W1 C1 1.957(16) . ? W1 C3 1.998(15) . ? W1 O4 2.155(8) 3_777 ? W1 N1 2.211(11) . ? W1 O4 2.223(8) . ? W1 C4 2.223(12) 3_777 ? N1 C11 1.342(16) . ? N1 C15 1.347(15) . ? C1 O1 1.164(15) . ? C2 O2 1.161(17) . ? C3 O3 1.146(15) . ? O4 C4 1.378(13) . ? O4 W1 2.155(8) 3_777 ? C4 C15 1.466(16) . ? C4 W1 2.223(12) 3_777 ? C11 C12 1.354(19) . ? C12 C13 1.37(2) . ? C13 C14 1.365(19) . ? C14 C15 1.362(18) . ? 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 W1 C1 94.1(6) . . ? C2 W1 C3 81.8(5) . . ? C1 W1 C3 78.6(5) . . ? C2 W1 O4 95.2(4) . 3_777 ? C1 W1 O4 111.3(4) . 3_777 ? C3 W1 O4 169.9(5) . 3_777 ? C2 W1 N1 100.5(5) . . ? C1 W1 N1 156.2(4) . . ? C3 W1 N1 85.0(5) . . ? O4 W1 N1 86.1(3) 3_777 . ? C2 W1 O4 168.7(4) . . ? C1 W1 O4 94.2(4) . . ? C3 W1 O4 107.3(4) . . ? O4 W1 O4 74.7(3) 3_777 . ? N1 W1 O4 74.3(3) . . ? C2 W1 C4 84.3(5) . 3_777 ? C1 W1 C4 77.3(5) . 3_777 ? C3 W1 C4 151.1(5) . 3_777 ? O4 W1 C4 36.6(3) 3_777 3_777 ? N1 W1 C4 122.5(4) . 3_777 ? O4 W1 C4 90.1(4) . 3_777 ? C11 N1 C15 117.7(12) . . ? C11 N1 W1 125.1(9) . . ? C15 N1 W1 117.1(9) . . ? O1 C1 W1 179.4(13) . . ? O2 C2 W1 176.7(12) . . ? O3 C3 W1 175.9(12) . . ? C4 O4 W1 74.4(6) . 3_777 ? C4 O4 W1 114.6(7) . . ? W1 O4 W1 105.3(3) 3_777 . ? O4 C4 C15 116.3(10) . . ? O4 C4 W1 69.0(6) . 3_777 ? C15 C4 W1 121.1(9) . 3_777 ? N1 C11 C12 122.6(14) . . ? C11 C12 C13 120.0(15) . . ? C14 C13 C12 117.6(15) . . ? C15 C14 C13 120.9(14) . . ? N1 C15 C14 121.1(13) . . ? N1 C15 C4 115.9(11) . . ? C14 C15 C4 122.9(12) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.080 _refine_diff_density_min -1.433 _refine_diff_density_rms 0.270 #===END