Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_name_full 'Dalton Trans.' #=================================================================== # 0. AUDIT DETAILS _audit_creation_date 9-May-03 _audit_creation_method 'PLATON option' _audit_update_record ; 9-May-03 Updated by the Author E.H. Textwriting by E.H. Checkcif OK 12May-03 Updated by the Author E.H. ; _journal_coden_Cambridge 0222 loop_ _publ_author_name 'Fritz Elmar Kuhn' 'Eberhardt Herdtweck' 'Carlos C. Romao' 'Ana M. Santos' 'Jin Zhao' 'Xiangge Zhou' _publ_contact_author_name 'Dr Fritz Elmar Kuhn' _publ_contact_author_address ; Anorganische Chemie Technische Universitat Munchen Lichtenbergstr. 4 Garching b. Munchen Bayern 85747 GERMANY ; _publ_contact_author_email FRITZ.KUEHN@CH.TUM.DE _publ_section_title ; Molybdenum(VI) cis-dioxo complexes bearing sugar derived chiral Schiff base ligands: synthesis, characterization and catalytic applications ; _publ_section_abstract ; Molybdenum(VI)-cis-dioxo complexes bearing sugar derived chiral Schiff base ligands of general formula MoO2(L)(Solv) ; # Insert blank lines between references _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). SIR92, J. Appl. Cryst. 27, 435-436. Nonius (2001a). Data Collection Software for Nonius Kappa-CCD devices. Nonius BV, Delft, The Netherlands. Nonius (2001b). DENZO Processing Software for Nonius Kappa-CCD devices, Nonius BV, Delft, The Netherlands. Sheldrick, G. M. (1998). SHELXL97, University of Gottingen, Gottingen, Germany. Spek, A. L. (2001). PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; #=================================================================== data_ZHAD-4199-173 _database_code_CSD 211645 #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety '4(C21 H25 N O10), H2 O' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C84 H102 N4 O41' _chemical_formula_weight 1823.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 7.8853(1) _cell_length_b 15.8327(1) _cell_length_c 18.7171(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2336.75(4) _cell_formula_units_Z 1 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 2469 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 25.33 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method none _exptl_crystal_F_000 962 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details '(applied during the scaling procedure; Nonius, 2001b)' _exptl_special_details ; Diffractometer operator E. Herdtweck scanspeed 2 x 120 s per film repetition 1 dx 40 520 films measured in 9 data sets set 1: phi-scan with delta_phi = 2.0 set 2 to 9 omega-scans with delta_omega = 2.0 ; _publ_section_exptl_prep ; The crystal was fixed in a capillary with perfluorinated ether and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Straight forward after integration with the program NPROCESS, source: Nonius (2001b). Hydrogen atoms could be located in the difference Fourier maps and refined freely. A water molecule, occupancy 0.25; could be located and refined succesfully. ; #=================================================================== # 7. EXPERIMENTAL DATA #=================================================================== _diffrn_ambient_temperature 173(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'NONIUS FR 591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Nonius \k-CCD diffractometer' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 18 # 9 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 56775 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_sigmaI/netI 0.0143 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.33 _reflns_number_total 4268 _reflns_number_gt 4058 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Kappa-CCD Control Software (Nonius, 2001a)' _computing_cell_refinement 'DENZO (Nonius, 2001b)' _computing_data_reduction 'DENZO (Nonius, 2001b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material 'PLATON (Spek, 2001)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(Fo^2^)+(0.0316P)^2^+0.3862P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall ##### #except those located at the water molecule ##### _chemical_absolute_configuration syn _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(6) _refine_ls_number_reflns 4268 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0291 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0665 _refine_ls_wR_factor_gt 0.0647 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.106 _refine_diff_density_min -0.126 _refine_diff_density_rms 0.027 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.77021(12) 0.39577(6) 0.26255(5) 1.000 0.0334(3) . . O2 O Uani 0.50376(12) 0.45332(6) 0.24373(5) 1.000 0.0331(3) . . O3 O Uani 0.45733(17) 0.56197(8) 0.31741(8) 1.000 0.0709(5) . . O4 O Uani 0.72146(12) 0.43490(6) 0.04372(5) 1.000 0.0336(3) . . O5 O Uani 0.45876(14) 0.48217(7) 0.01749(6) 1.000 0.0444(3) . . O6 O Uani 0.66592(12) 0.27084(6) 0.10264(5) 1.000 0.0347(3) . . O7 O Uani 0.91326(14) 0.20883(7) 0.07320(6) 1.000 0.0504(4) . . O8 O Uani 1.01659(11) 0.27291(6) 0.22758(5) 1.000 0.0362(3) . . O9 O Uani 1.08194(13) 0.13518(6) 0.22926(7) 1.000 0.0479(4) . . O10 O Uani 0.42149(19) 0.68600(9) 0.14315(8) 1.000 0.0723(5) . . N N Uani 0.65909(15) 0.57219(7) 0.14493(6) 1.000 0.0332(3) . . C1 C Uani 0.68480(16) 0.46898(8) 0.24115(7) 1.000 0.0311(4) . . C2 C Uani 0.73242(18) 0.49141(8) 0.16456(7) 1.000 0.0308(4) . . C3 C Uani 0.67004(17) 0.41991(8) 0.11667(7) 1.000 0.0295(4) . . C4 C Uani 0.75167(16) 0.33798(8) 0.14015(7) 1.000 0.0298(4) . . C5 C Uani 0.73110(17) 0.32209(8) 0.22064(7) 1.000 0.0313(4) . . C6 C Uani 0.84447(17) 0.25200(9) 0.24708(9) 1.000 0.0364(4) . . C7 C Uani 0.40441(19) 0.50415(9) 0.28329(9) 1.000 0.0396(4) . . C8 C Uani 0.2227(2) 0.47854(13) 0.27834(14) 1.000 0.0591(7) . . C9 C Uani 0.6011(2) 0.46611(9) -0.00110(8) 1.000 0.0366(4) . . C10 C Uani 0.6692(3) 0.47650(14) -0.07495(9) 1.000 0.0556(6) . . C11 C Uani 0.76108(19) 0.21145(8) 0.06883(7) 1.000 0.0354(4) . . C12 C Uani 0.6511(2) 0.15285(11) 0.02786(10) 1.000 0.0475(5) . . C13 C Uani 1.12119(17) 0.20715(9) 0.21730(8) 1.000 0.0384(4) . . C14 C Uani 1.2882(2) 0.23604(13) 0.18909(16) 1.000 0.0636(8) . . C15 C Uani 0.7564(2) 0.62605(9) 0.11576(8) 1.000 0.0404(5) . . C16 C Uani 0.6992(3) 0.71057(9) 0.09649(8) 1.000 0.0490(6) . . C17 C Uani 0.5341(3) 0.73734(10) 0.11156(9) 1.000 0.0573(6) . . C18 C Uani 0.4846(4) 0.82007(12) 0.09444(11) 1.000 0.0801(8) . . C19 C Uani 0.5974(5) 0.87289(12) 0.06145(12) 1.000 0.0916(11) . . C20 C Uani 0.7582(5) 0.84738(13) 0.04521(14) 1.000 0.0959(12) . . C21 C Uani 0.8115(4) 0.76656(12) 0.06327(12) 1.000 0.0743(8) . . O O Uani 0.1712(9) 0.5425(5) 0.1091(4) 0.250 0.098(3) . . H H Uiso 0.472(3) 0.6352(17) 0.1512(14) 1.000 0.097(8) . . H11 H Uiso 0.7113(18) 0.5127(9) 0.2743(8) 1.000 0.028(3) . . H21 H Uiso 0.8559(18) 0.4929(8) 0.1618(7) 1.000 0.023(3) . . H31 H Uiso 0.5485(17) 0.4144(8) 0.1187(6) 1.000 0.016(3) . . H41 H Uiso 0.8703(19) 0.3386(9) 0.1280(8) 1.000 0.029(3) . . H51 H Uiso 0.6124(19) 0.3050(9) 0.2306(7) 1.000 0.027(3) . . H61 H Uiso 0.8350(18) 0.2477(9) 0.3010(8) 1.000 0.030(4) . . H62 H Uiso 0.8110(19) 0.1978(10) 0.2256(8) 1.000 0.032(4) . . H81 H Uiso 0.201(3) 0.4213(17) 0.2930(12) 1.000 0.083(7) . . H82 H Uiso 0.189(4) 0.478(2) 0.2322(18) 1.000 0.131(12) . . H83 H Uiso 0.157(4) 0.517(2) 0.3136(19) 1.000 0.146(12) . . H101 H Uiso 0.792(4) 0.4778(16) -0.0755(13) 1.000 0.091(8) . . H102 H Uiso 0.629(3) 0.5320(17) -0.0912(15) 1.000 0.103(9) . . H103 H Uiso 0.617(4) 0.4352(17) -0.1055(16) 1.000 0.107(9) . . H121 H Uiso 0.565(4) 0.1261(19) 0.0577(19) 1.000 0.137(12) . . H122 H Uiso 0.708(3) 0.1115(16) 0.0068(13) 1.000 0.091(8) . . H123 H Uiso 0.597(3) 0.1816(16) -0.0069(14) 1.000 0.090(8) . . H141 H Uiso 1.313(3) 0.2885(18) 0.2030(13) 1.000 0.093(8) . . H142 H Uiso 1.281(4) 0.2440(16) 0.1380(17) 1.000 0.106(10) . . H143 H Uiso 1.374(3) 0.1973(14) 0.1965(11) 1.000 0.072(6) . . H151 H Uiso 0.875(2) 0.6150(10) 0.1081(9) 1.000 0.043(4) . . H181 H Uiso 0.348(4) 0.836(2) 0.1058(18) 1.000 0.135(11) . . H191 H Uiso 0.559(3) 0.9318(16) 0.0502(13) 1.000 0.085(7) . . H201 H Uiso 0.834(4) 0.8829(18) 0.0249(16) 1.000 0.114(10) . . H211 H Uiso 0.931(3) 0.7416(16) 0.0570(14) 1.000 0.096(9) . . H1 H Uiso 0.17910 0.49460 0.07520 0.250 0.1180 calc R H2 H Uiso 0.25530 0.58620 0.09590 0.250 0.1180 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 O1 0.0329(5) 0.0312(4) 0.0360(5) 0.0013(4) -0.0041(4) 0.0011(4) O2 0.0290(4) 0.0315(5) 0.0389(5) -0.0041(4) 0.0042(4) 0.0011(4) O3 0.0594(8) 0.0621(8) 0.0911(10) -0.0407(8) 0.0269(7) -0.0081(7) O4 0.0338(5) 0.0341(5) 0.0330(5) 0.0004(4) 0.0020(4) 0.0040(4) O5 0.0419(6) 0.0419(6) 0.0495(6) 0.0031(5) -0.0073(5) 0.0076(5) O6 0.0311(5) 0.0275(5) 0.0454(5) -0.0056(4) -0.0003(4) 0.0008(4) O7 0.0411(6) 0.0460(6) 0.0640(7) -0.0139(5) 0.0035(5) 0.0084(5) O8 0.0262(4) 0.0294(5) 0.0531(6) 0.0041(4) -0.0027(4) 0.0011(4) O9 0.0412(5) 0.0307(5) 0.0719(8) 0.0068(5) -0.0063(5) 0.0046(4) O10 0.0798(9) 0.0492(7) 0.0878(10) 0.0251(7) 0.0388(8) 0.0282(7) N 0.0399(6) 0.0255(5) 0.0342(6) -0.0019(5) 0.0034(5) -0.0016(5) C1 0.0283(6) 0.0298(6) 0.0353(7) -0.0022(6) -0.0007(5) -0.0011(5) C2 0.0254(7) 0.0278(6) 0.0392(7) 0.0005(5) 0.0020(6) -0.0001(5) C3 0.0259(6) 0.0296(6) 0.0329(7) -0.0002(5) 0.0024(5) 0.0013(5) C4 0.0243(6) 0.0258(6) 0.0394(7) -0.0027(5) 0.0009(6) -0.0006(5) C5 0.0254(6) 0.0281(6) 0.0404(7) 0.0012(6) 0.0012(6) -0.0016(5) C6 0.0289(6) 0.0327(7) 0.0477(9) 0.0083(6) 0.0012(6) 0.0006(6) C7 0.0424(8) 0.0312(7) 0.0451(8) -0.0026(7) 0.0113(7) 0.0027(6) C8 0.0386(9) 0.0532(11) 0.0856(15) -0.0062(11) 0.0162(10) 0.0049(8) C9 0.0432(8) 0.0265(6) 0.0401(7) 0.0001(6) -0.0060(6) -0.0006(6) C10 0.0672(13) 0.0617(11) 0.0380(9) 0.0066(8) -0.0019(9) -0.0006(10) C11 0.0401(8) 0.0271(6) 0.0391(7) 0.0024(5) 0.0031(6) 0.0046(6) C12 0.0556(10) 0.0364(8) 0.0505(10) -0.0099(8) -0.0037(8) 0.0041(8) C13 0.0305(7) 0.0361(8) 0.0486(8) 0.0008(7) -0.0081(6) 0.0048(6) C14 0.0296(8) 0.0451(10) 0.116(2) -0.0004(11) 0.0070(10) 0.0022(8) C15 0.0490(9) 0.0326(7) 0.0397(8) -0.0042(6) 0.0080(7) -0.0080(7) C16 0.0803(13) 0.0274(7) 0.0392(8) -0.0022(6) 0.0123(8) -0.0093(7) C17 0.0984(15) 0.0322(8) 0.0414(9) 0.0033(7) 0.0197(9) 0.0118(9) C18 0.145(2) 0.0367(9) 0.0587(11) 0.0072(8) 0.0273(13) 0.0284(12) C19 0.185(3) 0.0274(9) 0.0624(13) 0.0040(9) 0.0228(16) 0.0089(14) C20 0.167(3) 0.0389(11) 0.0817(16) 0.0118(11) 0.0263(19) -0.0279(16) C21 0.1071(19) 0.0419(10) 0.0739(13) 0.0065(9) 0.0188(13) -0.0242(11) O 0.078(4) 0.119(6) 0.098(5) 0.007(4) 0.008(4) 0.008(4) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3991(16) . . yes O1 C5 1.4392(16) . . yes O2 C1 1.4497(16) . . yes O2 C7 1.3452(18) . . yes O3 C7 1.192(2) . . yes O4 C3 1.4440(16) . . yes O4 C9 1.3597(18) . . yes O5 C9 1.2023(19) . . yes O6 C4 1.4423(16) . . yes O6 C11 1.3593(16) . . yes O7 C11 1.2035(19) . . yes O8 C6 1.4439(16) . . yes O8 C13 1.3421(17) . . yes O9 C13 1.2018(17) . . yes O10 C17 1.341(2) . . yes O10 H 0.91(3) . . no O H1 0.9908 . . no O H2 0.9897 . . no N C15 1.2705(19) . . yes N C2 1.4509(17) . . yes C1 C2 1.5239(19) . . no C2 C3 1.5254(18) . . no C3 C4 1.5133(18) . . no C4 C5 1.5360(19) . . no C5 C6 1.5085(19) . . no C7 C8 1.492(2) . . no C9 C10 1.492(2) . . no C11 C12 1.484(2) . . no C13 C14 1.491(2) . . no C15 C16 1.457(2) . . no C16 C21 1.399(3) . . no C16 C17 1.398(3) . . no C17 C18 1.404(3) . . no C18 C19 1.368(4) . . no C19 C20 1.365(5) . . no C20 C21 1.389(3) . . no C1 H11 0.953(15) . . no C2 H21 0.975(14) . . no C3 H31 0.963(13) . . no C4 H41 0.963(15) . . no C5 H51 0.992(15) . . no C6 H61 1.014(15) . . no C6 H62 0.984(16) . . no C8 H82 0.90(3) . . no C8 H81 0.96(3) . . no C8 H83 1.04(3) . . no C10 H103 0.96(3) . . no C10 H102 0.98(3) . . no C10 H101 0.97(3) . . no C12 H121 0.98(3) . . no C12 H122 0.89(2) . . no C12 H123 0.90(3) . . no C14 H141 0.89(3) . . no C14 H143 0.92(2) . . no C14 H142 0.97(3) . . no C15 H151 0.962(16) . . no C18 H181 1.13(3) . . no C19 H191 1.00(3) . . no C20 H201 0.90(3) . . no C21 H211 1.03(2) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C5 114.35(10) . . . yes C1 O2 C7 119.31(11) . . . yes C3 O4 C9 116.56(11) . . . yes C4 O6 C11 118.53(10) . . . yes C6 O8 C13 115.85(10) . . . yes C17 O10 H 108.6(15) . . . no H1 O H2 109.46 . . . no C2 N C15 117.37(12) . . . yes O2 C1 C2 108.29(10) . . . yes O1 C1 O2 108.83(10) . . . yes O1 C1 C2 110.11(10) . . . yes N C2 C3 112.14(11) . . . yes N C2 C1 110.21(11) . . . yes C1 C2 C3 107.48(10) . . . no O4 C3 C4 107.22(10) . . . yes O4 C3 C2 110.07(10) . . . yes C2 C3 C4 109.17(11) . . . no C3 C4 C5 112.35(11) . . . no O6 C4 C5 107.89(10) . . . yes O6 C4 C3 106.92(10) . . . yes O1 C5 C4 112.28(10) . . . yes O1 C5 C6 106.89(11) . . . yes C4 C5 C6 112.31(11) . . . no O8 C6 C5 107.78(11) . . . yes O3 C7 C8 125.33(16) . . . yes O2 C7 O3 123.41(14) . . . yes O2 C7 C8 111.25(14) . . . yes O4 C9 C10 111.13(14) . . . yes O4 C9 O5 123.36(14) . . . yes O5 C9 C10 125.51(16) . . . yes O6 C11 C12 110.52(12) . . . yes O6 C11 O7 122.86(12) . . . yes O7 C11 C12 126.61(13) . . . yes O8 C13 C14 110.83(13) . . . yes O9 C13 C14 125.76(14) . . . yes O8 C13 O9 123.41(13) . . . yes N C15 C16 122.39(15) . . . yes C15 C16 C21 119.7(2) . . . no C15 C16 C17 121.11(16) . . . no C17 C16 C21 119.15(17) . . . no C16 C17 C18 119.7(2) . . . no O10 C17 C16 121.45(15) . . . yes O10 C17 C18 118.8(2) . . . yes C17 C18 C19 119.5(3) . . . no C18 C19 C20 121.6(2) . . . no C19 C20 C21 120.0(3) . . . no C16 C21 C20 120.0(3) . . . no O1 C1 H11 108.1(9) . . . no C2 C1 H11 112.9(9) . . . no O2 C1 H11 108.6(9) . . . no N C2 H21 111.3(8) . . . no C1 C2 H21 107.5(8) . . . no C3 C2 H21 108.0(8) . . . no O4 C3 H31 109.4(7) . . . no C2 C3 H31 111.4(7) . . . no C4 C3 H31 109.5(8) . . . no C3 C4 H41 109.6(9) . . . no C5 C4 H41 109.6(9) . . . no O6 C4 H41 110.4(9) . . . no O1 C5 H51 108.7(8) . . . no C6 C5 H51 107.3(8) . . . no C4 C5 H51 109.2(8) . . . no O8 C6 H61 109.6(8) . . . no C5 C6 H61 109.4(8) . . . no C5 C6 H62 110.4(9) . . . no H61 C6 H62 109.2(12) . . . no O8 C6 H62 110.4(9) . . . no C7 C8 H82 110(2) . . . no C7 C8 H83 106.3(18) . . . no C7 C8 H81 114.1(14) . . . no H81 C8 H83 106(2) . . . no H82 C8 H83 118(3) . . . no H81 C8 H82 102(2) . . . no C9 C10 H102 105.6(16) . . . no C9 C10 H103 108.8(18) . . . no C9 C10 H101 111.8(14) . . . no H101 C10 H103 116(2) . . . no H102 C10 H103 107(2) . . . no H101 C10 H102 107(2) . . . no C11 C12 H122 113.3(16) . . . no C11 C12 H123 109.5(16) . . . no H121 C12 H122 107(2) . . . no H121 C12 H123 108(2) . . . no H122 C12 H123 107(2) . . . no C11 C12 H121 112(2) . . . no C13 C14 H141 112.1(15) . . . no C13 C14 H143 113.0(14) . . . no H141 C14 H142 100(2) . . . no H141 C14 H143 114(2) . . . no H142 C14 H143 106(2) . . . no C13 C14 H142 109.8(19) . . . no C16 C15 H151 115.5(10) . . . no N C15 H151 121.9(10) . . . no C17 C18 H181 115.6(16) . . . no C19 C18 H181 124.7(16) . . . no C20 C19 H191 120.6(14) . . . no C18 C19 H191 117.8(14) . . . no C19 C20 H201 121.6(19) . . . no C21 C20 H201 118.4(19) . . . no C16 C21 H211 112.8(14) . . . no C20 C21 H211 127.1(14) . . . no # End of Crystallographic Information File #=================================================================== data_ZHAG-4241-173 _database_code_CSD 211646 #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C21 H24 Cl N O10' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C21 H24 Cl N O10' _chemical_formula_weight 485.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z _cell_length_a 12.2573(1) _cell_length_b 7.1473(1) _cell_length_c 14.4914(2) _cell_angle_alpha 90 _cell_angle_beta 113.2552(4) _cell_angle_gamma 90 _cell_volume 1166.40(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 2301 _cell_measurement_theta_min 1.53 _cell_measurement_theta_max 25.28 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.89 _exptl_crystal_size_mid 0.89 _exptl_crystal_size_min 0.66 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method none _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.829 _exptl_absorpt_correction_T_max 0.869 _exptl_absorpt_process_details '(applied during the scaling procedure; Nonius, 2001b)' _exptl_special_details ; Diffractometer operator E5 Herdtweck scanspeed 2 x 120 s per film repetition 1 dx 40 1065 films measured in 9 data sets set 1: phi-scan with delta_phi = 1.0 set 2 to 9 omega-scans with delta_omega = 1.0 ; _publ_section_exptl_prep ; The crystal was fixed in a capillary with perfluorinated ether and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Straight forward after integration with the program NPROCESS, source: Nonius (2001b). Hydrogen atoms could be located in the difference Fourier maps and refined freely. ; #=================================================================== # 7. EXPERIMENTAL DATA #=================================================================== _diffrn_ambient_temperature 173(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'NONIUS FR 591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Nonius \k-CCD diffractometer' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 18 # 9 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 25017 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.28 _reflns_number_total 4229 _reflns_number_gt 4183 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Kappa-CCD Control Software (Nonius, 2001a)' _computing_cell_refinement 'DENZO (Nonius, 2001b)' _computing_data_reduction 'DENZO (Nonius, 2001b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material 'PLATON (Spek, 2001)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(Fo^2^)+(0.0446P)^2^+0.2249P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _chemical_absolute_configuration syn _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(5) _refine_ls_number_reflns 4229 _refine_ls_number_parameters 394 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0269 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0714 _refine_ls_wR_factor_gt 0.0712 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.28 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.207 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.034 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cl Cl Uani 0.83289(5) 0.28286(9) -0.30005(3) 1.000 0.0574(2) . . O1 O Uani 0.76762(9) 0.18456(14) 0.35185(7) 1.000 0.0223(3) . . O2 O Uani 0.94663(8) 0.29853(15) 0.35159(7) 1.000 0.0242(3) . . O3 O Uani 1.04090(11) 0.04737(18) 0.44094(9) 1.000 0.0399(4) . . O4 O Uani 0.66426(8) 0.53069(14) 0.10581(7) 1.000 0.0201(3) . . O5 O Uani 0.71153(10) 0.83549(15) 0.13846(9) 1.000 0.0317(3) . . O6 O Uani 0.63583(8) 0.64735(13) 0.29502(7) 1.000 0.0214(3) . . O7 O Uani 0.45664(9) 0.64405(17) 0.16615(9) 1.000 0.0368(4) . . O8 O Uani 0.54066(9) 0.29923(16) 0.37128(7) 1.000 0.0272(3) . . O9 O Uani 0.47373(16) 0.4431(4) 0.47449(14) 1.000 0.0893(9) . . O10 O Uani 1.07167(10) 0.30896(19) 0.13919(9) 1.000 0.0347(3) . . N N Uani 0.86103(9) 0.28559(17) 0.14497(8) 1.000 0.0203(3) . . C1 C Uani 0.84268(12) 0.1884(2) 0.29931(10) 1.000 0.0208(4) . . C2 C Uani 0.78066(11) 0.27719(19) 0.19633(9) 1.000 0.0183(3) . . C3 C Uani 0.73705(12) 0.47422(18) 0.20706(10) 1.000 0.0183(3) . . C4 C Uani 0.66303(12) 0.46304(18) 0.26951(10) 1.000 0.0188(4) . . C5 C Uani 0.73255(13) 0.3684(2) 0.37014(11) 1.000 0.0220(4) . . C6 C Uani 0.66050(15) 0.3496(2) 0.43393(11) 1.000 0.0288(4) . . C7 C Uani 1.04109(12) 0.2109(2) 0.42266(11) 1.000 0.0262(4) . . C8 C Uani 1.13939(15) 0.3446(3) 0.47210(14) 1.000 0.0347(5) . . C9 C Uani 0.65921(12) 0.7140(2) 0.08128(11) 1.000 0.0229(4) . . C10 C Uani 0.57909(18) 0.7395(3) -0.02707(14) 1.000 0.0391(5) . . C11 C Uani 0.52824(13) 0.7198(2) 0.23916(11) 1.000 0.0247(4) . . C12 C Uani 0.51265(16) 0.9036(2) 0.28069(15) 1.000 0.0332(5) . . C13 C Uani 0.45506(17) 0.3554(3) 0.39970(15) 1.000 0.0429(6) . . C14 C Uani 0.33608(18) 0.2950(4) 0.32606(19) 1.000 0.0559(8) . . C15 C Uani 0.81683(12) 0.26454(19) 0.04978(10) 1.000 0.0207(4) . . C16 C Uani 0.88997(12) 0.2790(2) -0.00846(10) 1.000 0.0226(4) . . C17 C Uani 1.01432(12) 0.3005(2) 0.03856(11) 1.000 0.0262(4) . . C18 C Uani 1.07959(15) 0.3117(2) -0.02082(14) 1.000 0.0356(5) . . C19 C Uani 1.02480(16) 0.3059(3) -0.12403(14) 1.000 0.0371(5) . . C20 C Uani 0.90300(15) 0.2870(3) -0.16908(12) 1.000 0.0343(5) . . C21 C Uani 0.83534(14) 0.2719(2) -0.11317(11) 1.000 0.0287(4) . . H H Uiso 1.023(2) 0.309(4) 0.1623(16) 1.000 0.042(6) . . H11 H Uiso 0.8667(14) 0.048(2) 0.2951(12) 1.000 0.018(4) . . H21 H Uiso 0.7138(14) 0.203(2) 0.1592(12) 1.000 0.014(4) . . H31 H Uiso 0.7977(16) 0.555(3) 0.2318(13) 1.000 0.020(4) . . H41 H Uiso 0.5907(14) 0.400(2) 0.2326(11) 1.000 0.012(4) . . H51 H Uiso 0.8016(14) 0.445(2) 0.4054(12) 1.000 0.014(4) . . H61 H Uiso 0.6952(16) 0.254(3) 0.4835(15) 1.000 0.033(5) . . H62 H Uiso 0.6602(17) 0.467(3) 0.4656(15) 1.000 0.034(5) . . H81 H Uiso 1.136(2) 0.433(4) 0.427(2) 1.000 0.060(7) . . H82 H Uiso 1.211(2) 0.289(4) 0.4984(18) 1.000 0.062(7) . . H83 H Uiso 1.120(2) 0.398(4) 0.524(2) 1.000 0.071(8) . . H101 H Uiso 0.600(2) 0.653(5) -0.072(2) 1.000 0.070(8) . . H102 H Uiso 0.581(3) 0.854(5) -0.048(2) 1.000 0.077(9) . . H103 H Uiso 0.510(3) 0.710(6) -0.037(3) 1.000 0.101(11) . . H121 H Uiso 0.577(2) 0.980(3) 0.2883(16) 1.000 0.043(6) . . H122 H Uiso 0.513(2) 0.894(3) 0.3473(18) 1.000 0.048(6) . . H123 H Uiso 0.438(2) 0.965(3) 0.2318(17) 1.000 0.049(6) . . H141 H Uiso 0.276(3) 0.367(5) 0.334(2) 1.000 0.081(9) . . H142 H Uiso 0.312(3) 0.184(6) 0.330(2) 1.000 0.084(11) . . H143 H Uiso 0.334(2) 0.279(4) 0.262(2) 1.000 0.066(7) . . H151 H Uiso 0.7323(14) 0.237(2) 0.0092(12) 1.000 0.016(4) . . H181 H Uiso 1.156(2) 0.334(3) 0.0092(16) 1.000 0.044(6) . . H191 H Uiso 1.0722(18) 0.317(3) -0.1677(15) 1.000 0.045(5) . . H211 H Uiso 0.7483(18) 0.254(3) -0.1429(14) 1.000 0.035(5) . . 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 Cl 0.0793(3) 0.0696(3) 0.0309(2) -0.0001(2) 0.0298(2) 0.0009(3) O1 0.0254(5) 0.0193(5) 0.0191(5) 0.0014(4) 0.0056(4) 0.0025(4) O2 0.0203(5) 0.0217(5) 0.0226(4) 0.0021(4) -0.0001(4) 0.0023(4) O3 0.0322(6) 0.0324(6) 0.0407(7) 0.0115(5) -0.0009(5) 0.0070(5) O4 0.0204(4) 0.0167(5) 0.0188(5) 0.0010(4) 0.0030(4) 0.0020(4) O5 0.0372(6) 0.0182(5) 0.0385(6) 0.0008(5) 0.0138(5) -0.0006(5) O6 0.0207(5) 0.0172(5) 0.0230(5) -0.0058(4) 0.0052(4) 0.0018(4) O7 0.0237(5) 0.0360(7) 0.0379(7) -0.0129(5) -0.0015(5) 0.0077(5) O8 0.0310(5) 0.0268(5) 0.0275(5) -0.0056(5) 0.0156(4) -0.0001(5) O9 0.0624(11) 0.146(2) 0.0695(12) -0.0605(13) 0.0368(9) -0.0038(11) O10 0.0210(5) 0.0418(7) 0.0376(6) -0.0038(6) 0.0075(5) -0.0023(5) N 0.0189(5) 0.0171(5) 0.0221(5) -0.0006(5) 0.0050(4) 0.0022(5) C1 0.0201(6) 0.0178(6) 0.0201(7) -0.0002(6) 0.0033(5) 0.0019(5) C2 0.0161(6) 0.0156(6) 0.0194(6) -0.0028(6) 0.0029(5) 0.0003(5) C3 0.0171(6) 0.0157(6) 0.0162(6) -0.0018(5) 0.0002(5) 0.0000(5) C4 0.0175(6) 0.0150(6) 0.0196(7) -0.0043(5) 0.0027(5) 0.0007(5) C5 0.0233(7) 0.0208(7) 0.0175(7) -0.0033(5) 0.0033(6) 0.0003(6) C6 0.0351(8) 0.0310(8) 0.0184(7) -0.0031(6) 0.0086(6) 0.0010(7) C7 0.0200(7) 0.0363(9) 0.0188(7) 0.0022(6) 0.0039(6) 0.0080(6) C8 0.0220(8) 0.0437(10) 0.0317(9) -0.0005(8) 0.0034(7) 0.0020(7) C9 0.0202(6) 0.0202(7) 0.0289(8) 0.0054(6) 0.0103(6) 0.0052(6) C10 0.0371(9) 0.0352(10) 0.0341(9) 0.0173(7) 0.0025(7) 0.0063(8) C11 0.0216(7) 0.0238(7) 0.0279(8) -0.0030(6) 0.0090(6) 0.0034(6) C12 0.0314(9) 0.0247(8) 0.0418(10) -0.0075(7) 0.0126(7) 0.0055(7) C13 0.0452(10) 0.0522(11) 0.0398(10) -0.0092(8) 0.0259(8) 0.0041(8) C14 0.0362(10) 0.0731(17) 0.0674(14) -0.0221(14) 0.0301(10) -0.0020(12) C15 0.0182(6) 0.0170(6) 0.0239(7) 0.0000(5) 0.0052(5) 0.0010(5) C16 0.0238(7) 0.0161(6) 0.0285(7) -0.0005(6) 0.0109(6) 0.0005(6) C17 0.0247(7) 0.0184(6) 0.0346(7) -0.0027(6) 0.0106(6) 0.0012(6) C18 0.0284(8) 0.0285(9) 0.0552(10) -0.0057(8) 0.0221(8) -0.0046(7) C19 0.0471(9) 0.0269(8) 0.0513(10) -0.0017(8) 0.0345(8) -0.0018(8) C20 0.0477(9) 0.0294(8) 0.0314(8) -0.0015(7) 0.0216(7) -0.0017(8) C21 0.0307(8) 0.0281(8) 0.0272(7) -0.0018(7) 0.0114(6) 0.0015(6) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl C20 1.7475(16) . . yes O1 C1 1.4071(19) . . yes O1 C5 1.4393(18) . . yes O2 C1 1.4334(18) . . yes O2 C7 1.3608(18) . . yes O3 C7 1.1986(19) . . yes O4 C3 1.4415(16) . . yes O4 C9 1.3525(17) . . yes O5 C9 1.1968(19) . . yes O6 C4 1.4424(16) . . yes O6 C11 1.3489(19) . . yes O7 C11 1.2040(19) . . yes O8 C6 1.435(2) . . yes O8 C13 1.331(3) . . yes O9 C13 1.193(3) . . yes O10 C17 1.3472(19) . . yes O10 H 0.79(3) . . no N C15 1.2763(17) . . yes N C2 1.4515(18) . . yes C1 C2 1.5205(18) . . no C2 C3 1.5358(19) . . no C3 C4 1.516(2) . . no C4 C5 1.526(2) . . no C5 C6 1.516(2) . . no C7 C8 1.482(3) . . no C9 C10 1.498(2) . . no C11 C12 1.488(2) . . no C13 C14 1.491(3) . . no C15 C16 1.457(2) . . no C16 C21 1.397(2) . . no C16 C17 1.411(2) . . no C17 C18 1.389(3) . . no C18 C19 1.377(3) . . no C19 C20 1.380(3) . . no C20 C21 1.373(3) . . no C1 H11 1.054(15) . . no C2 H21 0.946(16) . . no C3 H31 0.90(2) . . no C4 H41 0.949(16) . . no C5 H51 0.967(17) . . no C6 H61 0.96(2) . . no C6 H62 0.96(2) . . no C8 H81 0.90(3) . . no C8 H82 0.90(3) . . no C8 H83 0.95(3) . . no C10 H101 1.00(3) . . no C10 H102 0.88(4) . . no C10 H103 0.83(4) . . no C12 H121 0.93(2) . . no C12 H122 0.97(2) . . no C12 H123 1.01(2) . . no C14 H141 0.94(4) . . no C14 H142 0.86(4) . . no C14 H143 0.93(3) . . no C15 H151 0.988(18) . . no C18 H181 0.88(3) . . no C19 H191 1.02(2) . . no C21 H211 0.99(2) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C5 112.86(11) . . . yes C1 O2 C7 117.41(11) . . . yes C3 O4 C9 118.98(11) . . . yes C4 O6 C11 117.84(11) . . . yes C6 O8 C13 117.62(13) . . . yes C17 O10 H 107.4(16) . . . no C2 N C15 117.70(12) . . . yes O1 C1 C2 111.03(12) . . . yes O2 C1 C2 106.57(11) . . . yes O1 C1 O2 111.06(11) . . . yes N C2 C3 110.35(11) . . . yes C1 C2 C3 110.03(11) . . . no N C2 C1 110.06(12) . . . yes O4 C3 C2 104.71(10) . . . yes C2 C3 C4 109.05(11) . . . no O4 C3 C4 110.28(12) . . . yes O6 C4 C3 111.00(11) . . . yes C3 C4 C5 110.73(13) . . . no O6 C4 C5 104.97(11) . . . yes O1 C5 C6 108.64(12) . . . yes C4 C5 C6 112.46(13) . . . no O1 C5 C4 108.87(11) . . . yes O8 C6 C5 109.50(12) . . . yes O2 C7 C8 110.82(13) . . . yes O3 C7 C8 126.44(15) . . . yes O2 C7 O3 122.73(14) . . . yes O4 C9 C10 109.65(13) . . . yes O5 C9 C10 125.99(15) . . . yes O4 C9 O5 124.36(14) . . . yes O6 C11 O7 123.74(14) . . . yes O7 C11 C12 125.93(16) . . . yes O6 C11 C12 110.33(13) . . . yes O8 C13 O9 123.2(2) . . . yes O9 C13 C14 125.8(2) . . . yes O8 C13 C14 111.03(17) . . . yes N C15 C16 121.46(14) . . . yes C15 C16 C17 121.48(12) . . . no C15 C16 C21 119.07(14) . . . no C17 C16 C21 119.45(14) . . . no O10 C17 C16 122.01(14) . . . yes O10 C17 C18 119.07(15) . . . yes C16 C17 C18 118.92(14) . . . no C17 C18 C19 121.18(18) . . . no C18 C19 C20 119.30(18) . . . no Cl C20 C19 119.46(14) . . . yes C19 C20 C21 121.41(16) . . . no Cl C20 C21 119.13(14) . . . yes C16 C21 C20 119.72(16) . . . no O1 C1 H11 105.7(10) . . . no O2 C1 H11 110.1(10) . . . no C2 C1 H11 112.5(9) . . . no N C2 H21 110.0(11) . . . no C1 C2 H21 108.0(9) . . . no C3 C2 H21 108.3(10) . . . no O4 C3 H31 108.0(12) . . . no C2 C3 H31 111.4(13) . . . no C4 C3 H31 113.1(12) . . . no O6 C4 H41 108.6(10) . . . no C3 C4 H41 109.6(10) . . . no C5 C4 H41 111.9(9) . . . no O1 C5 H51 110.6(10) . . . no C4 C5 H51 107.2(9) . . . no C6 C5 H51 109.1(10) . . . no O8 C6 H61 109.6(13) . . . no O8 C6 H62 109.1(13) . . . no C5 C6 H61 109.1(13) . . . no C5 C6 H62 109.2(13) . . . no H61 C6 H62 110.5(17) . . . no C7 C8 H81 107.9(17) . . . no C7 C8 H82 113.0(18) . . . no C7 C8 H83 103.4(17) . . . no H81 C8 H82 112(2) . . . no H81 C8 H83 110(2) . . . no H82 C8 H83 110(2) . . . no C9 C10 H101 112.1(16) . . . no C9 C10 H102 112.3(19) . . . no C9 C10 H103 111(3) . . . no H101 C10 H102 108(3) . . . no H101 C10 H103 104(3) . . . no H102 C10 H103 110(4) . . . no C11 C12 H121 109.2(14) . . . no C11 C12 H122 113.0(13) . . . no C11 C12 H123 109.0(13) . . . no H121 C12 H122 105(2) . . . no H121 C12 H123 108.6(19) . . . no H122 C12 H123 112(2) . . . no C13 C14 H141 110(2) . . . no C13 C14 H142 119(2) . . . no C13 C14 H143 112.7(17) . . . no H141 C14 H142 101(3) . . . no H141 C14 H143 118(2) . . . no H142 C14 H143 95(3) . . . no N C15 H151 124.4(10) . . . no C16 C15 H151 114.2(10) . . . no C17 C18 H181 117.8(15) . . . no C19 C18 H181 120.7(15) . . . no C18 C19 H191 121.3(12) . . . no C20 C19 H191 119.4(12) . . . no C16 C21 H211 116.8(12) . . . no C20 C21 H211 123.5(12) . . . no # End of Crystallographic Information File #=================================================================== data_ZHAH-4262-173 _database_code_CSD 211647 #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C21 H27 Mo N O12' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C21 H27 Mo N O12' _chemical_formula_weight 581.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' Mo Mo -1.6832 0.6857 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 16.0532(1) _cell_length_b 8.0234(1) _cell_length_c 18.8865(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2432.60(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 2569 _cell_measurement_theta_min 1.66 _cell_measurement_theta_max 25.34 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method none _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.603 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.710 _exptl_absorpt_correction_T_max 0.926 _exptl_absorpt_process_details '(applied during the scaling procedure; Nonius, 2001b)' _exptl_special_details ; Diffractometer operator E. Herdtweck scanspeed 2 x 5 s per film repetition 1 dx 40 1032 films measured in 8 data sets set 1: phi-scan with delta_phi = 1.0 set 2 to 8 omega-scans with delta_omega = 1.0 ; _publ_section_exptl_prep ; The crystal was fixed in a capillary with perfluorinated ether and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Straight forward after integration with the program NPROCESS, source: Nonius (2001b). Hydrogen atoms could be located in the difference Fourier maps and refined freely. ; #=================================================================== # 7. EXPERIMENTAL DATA #=================================================================== _diffrn_ambient_temperature 173(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'NONIUS FR 591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Nonius \k-CCD diffractometer' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 18 # 9 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 54662 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.0130 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.34 _reflns_number_total 4450 _reflns_number_gt 4386 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Kappa-CCD Control Software (Nonius, 2001a)' _computing_cell_refinement 'DENZO (Nonius, 2001b)' _computing_data_reduction 'DENZO (Nonius, 2001b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material 'PLATON (Spek, 2001)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(Fo^2^)+(0.0253P)^2^+0.7656P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _chemical_absolute_configuration syn _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.015(19) _refine_ls_number_reflns 4450 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0183 _refine_ls_R_factor_gt 0.0179 _refine_ls_wR_factor_ref 0.0457 _refine_ls_wR_factor_gt 0.0455 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.394 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.041 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Mo Mo Uani 0.76816(1) 0.19781(2) -0.01659(1) 1.000 0.0251(1) . . O1 O Uani 0.71528(9) 0.10690(17) 0.19497(7) 1.000 0.0306(4) . . O2 O Uani 0.77344(8) 0.17106(15) 0.08560(7) 1.000 0.0267(4) . . O4 O Uani 0.55000(8) 0.46095(17) 0.11985(8) 1.000 0.0260(4) . . O5 O Uani 0.60978(10) 0.7063(2) 0.09199(10) 1.000 0.0508(6) . . O6 O Uani 0.65782(8) 0.53516(17) 0.23943(7) 1.000 0.0264(4) . . O7 O Uani 0.53345(12) 0.5445(2) 0.29298(12) 1.000 0.0653(7) . . O8 O Uani 0.81556(9) 0.1858(2) 0.32166(7) 1.000 0.0349(4) . . O9 O Uani 0.81307(14) 0.3330(2) 0.42254(9) 1.000 0.0534(6) . . O10 O Uani 0.71875(8) 0.30073(19) -0.10041(7) 1.000 0.0314(4) . . O11 O Uani 0.75028(10) -0.00282(19) -0.03965(8) 1.000 0.0414(5) . . O12 O Uani 0.87206(8) 0.2311(2) -0.03152(8) 1.000 0.0361(4) . . O13 O Uani 0.76941(9) 0.47856(18) 0.01840(8) 1.000 0.0296(4) . . N N Uani 0.63455(9) 0.23254(18) 0.02239(9) 1.000 0.0242(4) . . C1 C Uani 0.70290(13) 0.1079(2) 0.12116(11) 1.000 0.0282(6) . . C2 C Uani 0.62724(11) 0.2113(3) 0.09922(10) 1.000 0.0256(5) . . C3 C Uani 0.62975(11) 0.3830(2) 0.13398(10) 1.000 0.0227(5) . . C4 C Uani 0.64353(12) 0.3690(2) 0.21300(10) 1.000 0.0255(5) . . C5 C Uani 0.72227(13) 0.2683(2) 0.22715(10) 1.000 0.0272(5) . . C6 C Uani 0.73283(16) 0.2415(3) 0.30609(11) 1.000 0.0386(7) . . C9 C Uani 0.54912(13) 0.6214(3) 0.09777(11) 1.000 0.0300(6) . . C10 C Uani 0.46196(17) 0.6749(4) 0.0817(2) 1.000 0.0531(10) . . C11 C Uani 0.59626(13) 0.6127(3) 0.27556(12) 1.000 0.0317(7) . . C12 C Uani 0.61721(16) 0.7907(3) 0.28858(13) 1.000 0.0364(7) . . C13 C Uani 0.84790(16) 0.2389(3) 0.38349(11) 1.000 0.0365(7) . . C14 C Uani 0.93212(19) 0.1668(5) 0.39645(16) 1.000 0.0553(10) . . C15 C Uani 0.56859(11) 0.2639(2) -0.01422(12) 1.000 0.0274(5) . . C16 C Uani 0.56888(11) 0.3020(3) -0.08883(10) 1.000 0.0281(6) . . C17 C Uani 0.64237(12) 0.3188(3) -0.12857(10) 1.000 0.0287(5) . . C18 C Uani 0.63729(15) 0.3627(3) -0.20014(12) 1.000 0.0405(8) . . C19 C Uani 0.56079(16) 0.3923(4) -0.23062(14) 1.000 0.0516(9) . . C20 C Uani 0.48719(15) 0.3786(4) -0.19222(13) 1.000 0.0476(8) . . C21 C Uani 0.49158(13) 0.3326(3) -0.12201(12) 1.000 0.0361(7) . . C22 C Uani 0.84088(14) 0.5496(3) 0.05444(15) 1.000 0.0419(8) . . C23 C Uani 0.82199(16) 0.7141(4) 0.08702(16) 1.000 0.0476(8) . . H H Uiso 0.7493(14) 0.532(3) -0.0027(12) 1.000 0.022(7) . . H11 H Uiso 0.6934(13) -0.009(3) 0.1096(11) 1.000 0.019(5) . . H21 H Uiso 0.5775(13) 0.155(3) 0.1137(11) 1.000 0.021(5) . . H31 H Uiso 0.6702(13) 0.447(2) 0.1124(11) 1.000 0.018(5) . . H41 H Uiso 0.5969(13) 0.323(3) 0.2363(11) 1.000 0.022(5) . . H51 H Uiso 0.7655(13) 0.333(2) 0.2080(10) 1.000 0.018(5) . . H61 H Uiso 0.7243(18) 0.346(3) 0.3317(15) 1.000 0.053(8) . . H62 H Uiso 0.6963(15) 0.160(3) 0.3232(12) 1.000 0.031(6) . . H101 H Uiso 0.444(4) 0.650(9) 0.044(4) 1.000 0.20(3) . . H102 H Uiso 0.459(2) 0.784(5) 0.0789(18) 1.000 0.075(11) . . H103 H Uiso 0.432(3) 0.651(6) 0.121(3) 1.000 0.111(16) . . H121 H Uiso 0.669(3) 0.808(6) 0.287(2) 1.000 0.108(15) . . H122 H Uiso 0.589(2) 0.828(5) 0.327(2) 1.000 0.087(12) . . H123 H Uiso 0.608(3) 0.840(6) 0.250(2) 1.000 0.104(15) . . H141 H Uiso 0.942(3) 0.042(6) 0.381(2) 1.000 0.105(14) . . H142 H Uiso 0.9385(19) 0.129(4) 0.4427(18) 1.000 0.065(9) . . H143 H Uiso 0.968(3) 0.245(5) 0.376(2) 1.000 0.104(14) . . H151 H Uiso 0.5161(13) 0.262(2) 0.0098(11) 1.000 0.027(5) . . H181 H Uiso 0.6827(17) 0.375(3) -0.2284(14) 1.000 0.045(7) . . H191 H Uiso 0.5585(18) 0.420(4) -0.2760(17) 1.000 0.052(8) . . H201 H Uiso 0.4415(17) 0.391(3) -0.2123(13) 1.000 0.037(7) . . H211 H Uiso 0.4397(16) 0.321(3) -0.0951(13) 1.000 0.038(6) . . H221 H Uiso 0.8875(18) 0.556(3) 0.0178(16) 1.000 0.055(7) . . H222 H Uiso 0.860(3) 0.469(5) 0.102(2) 1.000 0.114(15) . . H231 H Uiso 0.869(2) 0.754(4) 0.1108(17) 1.000 0.065(9) . . H232 H Uiso 0.7779(19) 0.709(4) 0.1208(16) 1.000 0.061(8) . . H233 H Uiso 0.802(2) 0.792(4) 0.0480(18) 1.000 0.079(10) . . 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 Mo 0.0169(1) 0.0323(1) 0.0262(1) -0.0049(1) 0.0015(1) 0.0028(1) O1 0.0350(8) 0.0260(6) 0.0309(7) 0.0073(6) 0.0036(6) 0.0038(6) O2 0.0208(6) 0.0283(7) 0.0310(6) -0.0011(5) 0.0038(6) 0.0029(6) O4 0.0187(6) 0.0282(7) 0.0312(7) 0.0015(6) 0.0020(5) 0.0036(5) O5 0.0361(9) 0.0363(8) 0.0801(13) 0.0181(10) -0.0009(8) 0.0008(8) O6 0.0227(7) 0.0297(7) 0.0269(7) -0.0032(6) 0.0027(5) 0.0019(5) O7 0.0430(10) 0.0563(11) 0.0965(16) -0.0347(11) 0.0369(11) -0.0118(9) O8 0.0361(8) 0.0447(8) 0.0238(6) -0.0002(7) -0.0003(6) 0.0144(7) O9 0.0880(14) 0.0366(9) 0.0356(8) -0.0097(7) 0.0080(9) 0.0050(9) O10 0.0204(7) 0.0480(8) 0.0257(6) -0.0020(6) 0.0015(5) -0.0003(7) O11 0.0409(9) 0.0380(8) 0.0452(9) -0.0126(6) -0.0012(7) 0.0057(6) O12 0.0191(6) 0.0560(9) 0.0332(8) -0.0035(7) 0.0030(5) 0.0025(6) O13 0.0234(6) 0.0304(7) 0.0349(7) 0.0040(7) -0.0010(8) -0.0013(6) N 0.0191(7) 0.0267(7) 0.0267(8) -0.0043(7) 0.0025(6) -0.0011(6) C1 0.0287(10) 0.0230(9) 0.0330(10) 0.0001(8) 0.0035(8) -0.0001(8) C2 0.0214(9) 0.0259(9) 0.0294(9) 0.0025(8) 0.0055(7) -0.0020(8) C3 0.0173(9) 0.0244(9) 0.0265(10) 0.0012(8) 0.0023(8) 0.0024(7) C4 0.0231(9) 0.0258(9) 0.0277(10) 0.0008(8) 0.0039(8) -0.0010(8) C5 0.0248(10) 0.0315(9) 0.0254(9) 0.0054(7) 0.0052(8) 0.0042(8) C6 0.0331(10) 0.0557(14) 0.0271(10) 0.0087(9) 0.0059(10) 0.0155(11) C9 0.0298(11) 0.0313(10) 0.0290(10) 0.0031(9) 0.0035(8) 0.0065(9) C10 0.0332(13) 0.0521(18) 0.074(2) 0.0204(16) 0.0037(13) 0.0183(12) C11 0.0239(11) 0.0402(12) 0.0310(11) -0.0054(9) 0.0022(8) 0.0056(9) C12 0.0365(12) 0.0379(12) 0.0348(12) -0.0056(11) -0.0029(10) 0.0063(11) C13 0.0532(14) 0.0314(11) 0.0250(10) 0.0044(9) 0.0016(9) -0.0022(10) C14 0.0487(16) 0.075(2) 0.0421(15) 0.0053(15) -0.0115(12) -0.0013(15) C15 0.0182(9) 0.0295(9) 0.0346(10) -0.0051(9) 0.0026(8) -0.0028(7) C16 0.0222(9) 0.0313(10) 0.0308(10) -0.0044(9) -0.0012(7) -0.0019(9) C17 0.0224(9) 0.0343(10) 0.0295(9) -0.0052(9) -0.0026(7) -0.0011(9) C18 0.0273(11) 0.0631(16) 0.0312(12) 0.0019(11) 0.0022(9) -0.0008(11) C19 0.0378(14) 0.086(2) 0.0310(13) 0.0049(14) -0.0075(10) -0.0061(13) C20 0.0265(11) 0.0761(18) 0.0403(13) 0.0035(13) -0.0124(10) 0.0004(12) C21 0.0218(10) 0.0488(14) 0.0378(11) -0.0032(10) -0.0034(9) -0.0007(9) C22 0.0278(11) 0.0416(13) 0.0563(15) -0.0050(12) -0.0022(11) -0.0069(9) C23 0.0387(13) 0.0484(15) 0.0558(15) -0.0093(14) -0.0094(12) -0.0029(13) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mo O2 1.9437(13) . . yes Mo O10 1.9538(14) . . yes Mo O11 1.6922(15) . . yes Mo O12 1.7125(13) . . yes Mo O13 2.3476(15) . . yes Mo N 2.2848(15) . . yes O1 C1 1.408(2) . . yes O1 C5 1.435(2) . . yes O2 C1 1.411(2) . . yes O4 C3 1.450(2) . . yes O4 C9 1.353(3) . . yes O5 C9 1.193(3) . . yes O6 C4 1.442(2) . . yes O6 C11 1.353(3) . . yes O7 C11 1.193(3) . . yes O8 C6 1.432(3) . . yes O8 C13 1.347(3) . . yes O9 C13 1.194(3) . . yes O10 C17 1.344(2) . . yes O13 C22 1.451(3) . . yes O13 H 0.67(2) . . no N C15 1.289(2) . . yes N C2 1.466(3) . . yes C1 C2 1.528(3) . . no C2 C3 1.527(3) . . no C3 C4 1.513(3) . . no C4 C5 1.524(3) . . no C5 C6 1.516(3) . . no C9 C10 1.495(4) . . no C11 C12 1.488(3) . . no C13 C14 1.491(4) . . no C15 C16 1.442(3) . . no C16 C21 1.412(3) . . no C16 C17 1.405(3) . . no C17 C18 1.399(3) . . no C18 C19 1.377(4) . . no C19 C20 1.391(4) . . no C20 C21 1.378(3) . . no C22 C23 1.487(4) . . no C1 H11 0.98(2) . . no C2 H21 0.96(2) . . no C3 H31 0.92(2) . . no C4 H41 0.94(2) . . no C5 H51 0.939(19) . . no C6 H61 0.98(3) . . no C6 H62 0.94(2) . . no C10 H101 0.79(7) . . no C10 H102 0.88(4) . . no C10 H103 0.90(5) . . no C12 H121 0.84(5) . . no C12 H122 0.91(4) . . no C12 H123 0.84(4) . . no C14 H141 1.05(5) . . no C14 H142 0.93(3) . . no C14 H143 0.94(4) . . no C15 H151 0.96(2) . . no C18 H181 0.91(3) . . no C19 H191 0.89(3) . . no C20 H201 0.83(3) . . no C21 H211 0.98(3) . . no C22 H221 1.02(3) . . no C22 H222 1.15(4) . . no C23 H231 0.93(3) . . no C23 H232 0.95(3) . . no C23 H233 1.02(3) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mo O10 150.33(6) . . . yes O2 Mo O11 99.09(6) . . . yes O2 Mo O12 97.95(6) . . . yes O2 Mo O13 79.98(5) . . . yes O2 Mo N 74.60(6) . . . yes O10 Mo O11 97.16(7) . . . yes O10 Mo O12 101.31(6) . . . yes O10 Mo O13 79.98(6) . . . yes O10 Mo N 80.12(6) . . . yes O11 Mo O12 105.74(8) . . . yes O11 Mo O13 170.64(7) . . . yes O11 Mo N 92.27(7) . . . yes O12 Mo O13 83.59(6) . . . yes O12 Mo N 161.51(7) . . . yes O13 Mo N 78.48(5) . . . yes C1 O1 C5 115.16(13) . . . yes Mo O2 C1 118.51(12) . . . yes C3 O4 C9 118.45(14) . . . yes C4 O6 C11 118.93(15) . . . yes C6 O8 C13 115.90(17) . . . yes Mo O10 C17 137.43(13) . . . yes Mo O13 C22 121.05(12) . . . yes C22 O13 H 114(2) . . . no Mo O13 H 116(2) . . . no Mo N C15 128.46(14) . . . yes Mo N C2 112.33(11) . . . yes C2 N C15 119.20(16) . . . yes O1 C1 C2 112.56(16) . . . yes O2 C1 C2 108.29(15) . . . yes O1 C1 O2 111.10(16) . . . yes C1 C2 C3 110.63(15) . . . no N C2 C1 105.54(15) . . . yes N C2 C3 108.58(17) . . . yes C2 C3 C4 111.17(14) . . . no O4 C3 C4 110.05(15) . . . yes O4 C3 C2 106.67(14) . . . yes O6 C4 C5 107.31(14) . . . yes C3 C4 C5 109.49(15) . . . no O6 C4 C3 107.22(13) . . . yes C4 C5 C6 109.91(17) . . . no O1 C5 C4 109.84(15) . . . yes O1 C5 C6 107.30(15) . . . yes O8 C6 C5 110.49(18) . . . yes O4 C9 C10 110.2(2) . . . yes O5 C9 C10 125.5(2) . . . yes O4 C9 O5 124.2(2) . . . yes O7 C11 C12 125.8(2) . . . yes O6 C11 O7 123.1(2) . . . yes O6 C11 C12 111.09(18) . . . yes O9 C13 C14 124.6(2) . . . yes O8 C13 C14 111.7(2) . . . yes O8 C13 O9 123.7(2) . . . yes N C15 C16 124.25(17) . . . yes C15 C16 C17 123.04(17) . . . no C15 C16 C21 117.89(17) . . . no C17 C16 C21 118.97(18) . . . no O10 C17 C16 122.97(17) . . . yes C16 C17 C18 119.43(19) . . . no O10 C17 C18 117.55(18) . . . yes C17 C18 C19 120.0(2) . . . no C18 C19 C20 121.7(2) . . . no C19 C20 C21 118.7(2) . . . no C16 C21 C20 121.2(2) . . . no O13 C22 C23 112.43(19) . . . yes O1 C1 H11 103.8(13) . . . no O2 C1 H11 111.4(12) . . . no C2 C1 H11 109.7(13) . . . no N C2 H21 113.9(13) . . . no C1 C2 H21 109.2(14) . . . no C3 C2 H21 109.0(14) . . . no O4 C3 H31 107.5(12) . . . no C2 C3 H31 109.3(11) . . . no C4 C3 H31 112.0(13) . . . no O6 C4 H41 109.1(14) . . . no C3 C4 H41 111.9(13) . . . no C5 C4 H41 111.6(14) . . . no O1 C5 H51 113.2(11) . . . no C4 C5 H51 104.6(11) . . . no C6 C5 H51 112.0(12) . . . no O8 C6 H61 107.2(17) . . . no O8 C6 H62 107.0(15) . . . no C5 C6 H61 110.4(16) . . . no C5 C6 H62 111.6(14) . . . no H61 C6 H62 110(2) . . . no C9 C10 H101 117(5) . . . no C9 C10 H102 110(2) . . . no C9 C10 H103 106(3) . . . no H101 C10 H102 100(6) . . . no H101 C10 H103 119(6) . . . no H102 C10 H103 103(4) . . . no C11 C12 H121 112(3) . . . no C11 C12 H122 110(2) . . . no C11 C12 H123 106(3) . . . no H121 C12 H122 118(4) . . . no H121 C12 H123 94(4) . . . no H122 C12 H123 117(4) . . . no C13 C14 H141 117(3) . . . no C13 C14 H142 112.4(19) . . . no C13 C14 H143 103(3) . . . no H141 C14 H142 86(3) . . . no H141 C14 H143 115(3) . . . no H142 C14 H143 123(3) . . . no N C15 H151 117.8(12) . . . no C16 C15 H151 118.0(12) . . . no C17 C18 H181 123.2(17) . . . no C19 C18 H181 116.8(17) . . . no C18 C19 H191 119.0(19) . . . no C20 C19 H191 119.3(19) . . . no C19 C20 H201 120.1(18) . . . no C21 C20 H201 121.1(18) . . . no C16 C21 H211 120.0(15) . . . no C20 C21 H211 118.7(15) . . . no O13 C22 H221 106.4(16) . . . no O13 C22 H222 111(2) . . . no C23 C22 H221 112.7(14) . . . no C23 C22 H222 103(2) . . . no H221 C22 H222 111(3) . . . no C22 C23 H231 109.8(19) . . . no C22 C23 H232 113.0(19) . . . no C22 C23 H233 108.0(19) . . . no H231 C23 H232 107(3) . . . no H231 C23 H233 113(3) . . . no H232 C23 H233 106(3) . . . no # End of Crystallographic Information File