data_TREN-1,2-HOQIO-cerium-complex _publ_contact_author_name 'Kenneth N. Raymond' _publ_contact_author_address ;Department of Chemistry University of California Berkeley, CA 947020-1460 ; _publ_contact_author_email raymond@sokrates.berkeley.edu _publ_contact_author_fax ++1-510-486-5283 loop_ _publ_author_name _publ_author_address 'Raymond, Kenneth N.' ;Department of Chemistry University of California Berkeley, CA 947020-1460 ; 'Seitz, Michael' ;Department of Chemistry University of California Berkeley, CA 947020-1460 ; 'Pluth, Michael D.' ;Department of Chemistry University of California Berkeley, CA 947020-1460 ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H32 Ce N7 O10, H2O' _chemical_formula_sum 'C36 H34 Ce N7 O11' _chemical_formula_weight 880.82 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' Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 12.341(2) _cell_length_b 26.649(4) _cell_length_c 10.6206(17) _cell_angle_alpha 90.00 _cell_angle_beta 96.753(3) _cell_angle_gamma 90.00 _cell_volume 3468.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 189(2) _cell_measurement_reflns_used 978 _cell_measurement_theta_min 2.463 _cell_measurement_theta_max 15.474 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1780 _exptl_absorpt_coefficient_mu 1.387 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.92 _exptl_absorpt_process_details 'SADABS (Bruker 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 189(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 'Siemens Smart CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 83.23 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19701 _diffrn_reflns_av_R_equivalents 0.0828 _diffrn_reflns_av_sigmaI/netI 0.1308 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 26.43 _reflns_number_total 7045 _reflns_number_gt 4123 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.059 (Bruker)' _computing_cell_refinement 'SAINT V7.07B (Bruker)' _computing_data_reduction 'SAINT V7.07B (Bruker)' _computing_structure_solution 'SIR-92 (Altomare, 1993)' _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^)+(0.0476P)^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 7045 _refine_ls_number_parameters 496 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0997 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 0.887 _refine_ls_restrained_S_all 0.887 _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 Ce1 Ce 0.66583(3) 0.385615(12) 0.81264(3) 0.02389(11) Uani 1 1 d . . . O5 O 0.8595(3) 0.38255(15) 0.7927(3) 0.0339(10) Uani 1 1 d . . . O10 O 0.5558(3) 0.41351(14) 0.9917(4) 0.0338(10) Uani 1 1 d . . . O2 O 0.6627(3) 0.41070(13) 0.5921(4) 0.0317(10) Uani 1 1 d . . . O3 O 0.6082(3) 0.47244(14) 0.7586(4) 0.0323(10) Uani 1 1 d . . . O6 O 0.7872(3) 0.42869(15) 0.9765(3) 0.0332(10) Uani 1 1 d . . . C23 C 0.9646(5) 0.44527(19) 1.0823(5) 0.0227(14) Uani 1 1 d . . . N5 N 0.9330(4) 0.40289(17) 0.8855(4) 0.0289(12) Uani 1 1 d . . . C24 C 0.8911(5) 0.4260(2) 0.9815(5) 0.0279(14) Uani 1 1 d . . . O4 O 1.1888(4) 0.38454(19) 0.7576(4) 0.0553(13) Uani 1 1 d . . . N4 N 1.0204(4) 0.37964(18) 0.6508(5) 0.0383(13) Uani 1 1 d . . . H4 H 0.9521 0.3761 0.6578 0.046 Uiso 1 1 calc R . . N3 N 0.6486(4) 0.45945(17) 0.5596(4) 0.0271(12) Uani 1 1 d . . . C15 C 1.0908(5) 0.3858(2) 0.7552(6) 0.0384(15) Uani 1 1 d . . . N2 N 0.7296(4) 0.39490(18) 0.3716(4) 0.0344(13) Uani 1 1 d . . . H2 H 0.7369 0.3875 0.4509 0.041 Uiso 1 1 calc R . . C14 C 1.0570(5) 0.3789(2) 0.5255(6) 0.0426(17) Uani 1 1 d . . . H14A H 1.1346 0.3860 0.5341 0.051 Uiso 1 1 calc R . . H14B H 1.0202 0.4055 0.4749 0.051 Uiso 1 1 calc R . . C4 C 0.6655(5) 0.4756(2) 0.4383(5) 0.0284(14) Uani 1 1 d . . . C17 C 1.1147(5) 0.4162(2) 0.9759(6) 0.0371(17) Uani 1 1 d . . . H17 H 1.1893 0.4124 0.9736 0.045 Uiso 1 1 calc R . . C16 C 1.0439(5) 0.3999(2) 0.8766(6) 0.0325(15) Uani 1 1 d . . . C22 C 0.9250(5) 0.4711(2) 1.1830(6) 0.0362(16) Uani 1 1 d . . . H22 H 0.8505 0.4764 1.1823 0.043 Uiso 1 1 calc R . . C18 C 1.0763(5) 0.4390(2) 1.0833(6) 0.0327(15) Uani 1 1 d . . . C3 C 0.6898(5) 0.4390(2) 0.3372(6) 0.0350(16) Uani 1 1 d . . . O1 O 0.6713(4) 0.45358(16) 0.2234(4) 0.0418(12) Uani 1 1 d . . . N1 N 0.9209(4) 0.31951(17) 0.4145(4) 0.0314(12) Uani 1 1 d . . . C1 C 0.8838(5) 0.3490(2) 0.2991(5) 0.0370(16) Uani 1 1 d . . . H1A H 0.9038 0.3314 0.2253 0.044 Uiso 1 1 calc R . . H1B H 0.9209 0.3812 0.3039 0.044 Uiso 1 1 calc R . . C13 C 1.0366(5) 0.3297(2) 0.4554(6) 0.0363(16) Uani 1 1 d . . . H13A H 1.0758 0.3300 0.3814 0.044 Uiso 1 1 calc R . . H13B H 1.0661 0.3026 0.5100 0.044 Uiso 1 1 calc R . . C12 C 0.6179(5) 0.4912(2) 0.6503(5) 0.0269(14) Uani 1 1 d . . . C5 C 0.6572(5) 0.5254(2) 0.4108(6) 0.0343(16) Uani 1 1 d . . . H5 H 0.6703 0.5365 0.3309 0.041 Uiso 1 1 calc R . . C11 C 0.6055(5) 0.5432(2) 0.6190(5) 0.0259(14) Uani 1 1 d . . . C7 C 0.6240(5) 0.6119(2) 0.4768(6) 0.0385(15) Uani 1 1 d . . . H7 H 0.6428 0.6241 0.4003 0.046 Uiso 1 1 calc R . . C9 C 0.5625(5) 0.6265(2) 0.6773(6) 0.0414(18) Uani 1 1 d . . . H9 H 0.5369 0.6487 0.7345 0.050 Uiso 1 1 calc R . . C10 C 0.5708(5) 0.5764(2) 0.7065(6) 0.0354(16) Uani 1 1 d . . . H10 H 0.5532 0.5649 0.7842 0.042 Uiso 1 1 calc R . . C25 C 0.9043(5) 0.2657(2) 0.3908(6) 0.0345(16) Uani 1 1 d . . . H25A H 0.9668 0.2521 0.3548 0.041 Uiso 1 1 calc R . . H25B H 0.8403 0.2609 0.3297 0.041 Uiso 1 1 calc R . . C21 C 0.9967(5) 0.4884(2) 1.2826(6) 0.0357(16) Uani 1 1 d . . . H21 H 0.9708 0.5054 1.3494 0.043 Uiso 1 1 calc R . . C8 C 0.5915(6) 0.6442(2) 0.5647(6) 0.0431(18) Uani 1 1 d . . . H8 H 0.5890 0.6785 0.5481 0.052 Uiso 1 1 calc R . . C2 C 0.7623(5) 0.3577(2) 0.2830(5) 0.0397(17) Uani 1 1 d . . . H2A H 0.7395 0.3689 0.1970 0.048 Uiso 1 1 calc R . . H2B H 0.7255 0.3263 0.2957 0.048 Uiso 1 1 calc R . . C19 C 1.1478(6) 0.4566(3) 1.1852(6) 0.0463(18) Uani 1 1 d . . . H19 H 1.2227 0.4521 1.1867 0.056 Uiso 1 1 calc R . . C6 C 0.6289(5) 0.5609(2) 0.5020(6) 0.0313(15) Uani 1 1 d . . . O9 O 0.5001(3) 0.33476(13) 0.7712(3) 0.0274(9) Uani 1 1 d . . . O8 O 0.6796(3) 0.30943(14) 0.6873(4) 0.0314(10) Uani 1 1 d . . . N7 N 0.5904(4) 0.28010(16) 0.6579(4) 0.0231(11) Uani 1 1 d . . . C26 C 0.8896(5) 0.2380(2) 0.5094(5) 0.0314(15) Uani 1 1 d . . . H26A H 0.8927 0.2022 0.4933 0.038 Uiso 1 1 calc R . . H26B H 0.9493 0.2462 0.5739 0.038 Uiso 1 1 calc R . . C30 C 0.4034(5) 0.22273(19) 0.5972(5) 0.0249(14) Uani 1 1 d . . . C36 C 0.4969(5) 0.2950(2) 0.7064(5) 0.0281(14) Uani 1 1 d . . . C35 C 0.4013(5) 0.2643(2) 0.6764(5) 0.0256(14) Uani 1 1 d . . . C34 C 0.3047(5) 0.2771(2) 0.7244(5) 0.0310(15) Uani 1 1 d . . . H34 H 0.3023 0.3054 0.7751 0.037 Uiso 1 1 calc R . . C28 C 0.5955(5) 0.23782(19) 0.5820(5) 0.0243(14) Uani 1 1 d . . . C20 C 1.1066(6) 0.4805(3) 1.2829(6) 0.049(2) Uani 1 1 d . . . H20 H 1.1543 0.4917 1.3514 0.059 Uiso 1 1 calc R . . N6 N 0.7880(4) 0.24950(17) 0.5568(4) 0.0287(12) Uani 1 1 d . . . H6 H 0.7844 0.2758 0.6029 0.034 Uiso 1 1 calc R . . C32 C 0.2161(5) 0.2062(2) 0.6183(6) 0.0419(17) Uani 1 1 d . . . H32 H 0.1537 0.1867 0.5996 0.050 Uiso 1 1 calc R . . C31 C 0.3080(5) 0.1943(2) 0.5699(6) 0.0357(16) Uani 1 1 d . . . H31 H 0.3086 0.1665 0.5170 0.043 Uiso 1 1 calc R . . C33 C 0.2142(5) 0.2483(2) 0.6976(6) 0.0428(17) Uani 1 1 d . . . H33 H 0.1506 0.2566 0.7319 0.051 Uiso 1 1 calc R . . O7 O 0.6996(3) 0.18125(14) 0.4747(4) 0.0315(10) Uani 1 1 d . . . C27 C 0.6998(5) 0.2213(2) 0.5324(5) 0.0267(14) Uani 1 1 d . . . O11 O 0.3712(4) 0.47158(17) 0.9787(5) 0.0620(15) Uani 1 1 d . . . C29 C 0.5035(5) 0.2098(2) 0.5528(5) 0.0267(14) Uani 1 1 d . . . H29 H 0.5066 0.1815 0.5022 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ce1 0.02990(19) 0.02271(16) 0.01909(17) -0.00227(18) 0.00294(12) -0.00299(19) O5 0.034(2) 0.044(2) 0.023(2) -0.010(2) 0.0015(18) -0.009(2) O10 0.045(3) 0.032(2) 0.026(2) -0.0015(19) 0.0083(19) -0.001(2) O2 0.047(3) 0.021(2) 0.027(2) 0.0012(18) 0.004(2) 0.0020(19) O3 0.044(3) 0.033(2) 0.019(2) -0.0049(19) 0.0008(19) 0.001(2) O6 0.029(3) 0.045(3) 0.026(2) -0.007(2) 0.0020(19) -0.003(2) C23 0.031(4) 0.016(3) 0.020(3) 0.007(3) -0.001(3) -0.004(3) N5 0.033(3) 0.026(3) 0.027(3) 0.006(2) 0.002(2) -0.004(2) C24 0.040(4) 0.026(3) 0.018(3) 0.003(3) 0.008(3) -0.002(3) O4 0.034(3) 0.077(3) 0.057(3) -0.006(3) 0.010(2) 0.015(3) N4 0.035(3) 0.046(3) 0.035(3) -0.001(3) 0.010(2) -0.011(3) N3 0.031(3) 0.027(3) 0.022(3) -0.004(2) 0.000(2) 0.001(2) C15 0.040(4) 0.034(3) 0.042(4) -0.001(4) 0.008(3) 0.009(4) N2 0.049(3) 0.037(3) 0.016(3) 0.001(2) -0.003(2) 0.009(3) C14 0.031(4) 0.053(4) 0.048(4) -0.005(4) 0.022(3) -0.006(3) C4 0.025(4) 0.043(4) 0.017(3) 0.003(3) 0.000(3) 0.001(3) C17 0.027(4) 0.031(4) 0.051(5) 0.012(3) -0.005(3) 0.003(3) C16 0.037(4) 0.025(3) 0.035(4) 0.005(3) 0.005(3) 0.000(3) C22 0.039(4) 0.028(3) 0.040(4) 0.001(3) 0.001(3) -0.002(3) C18 0.031(4) 0.029(3) 0.037(4) 0.005(3) 0.001(3) -0.004(3) C3 0.038(4) 0.044(4) 0.023(4) 0.000(3) 0.005(3) -0.003(3) O1 0.063(3) 0.043(3) 0.022(3) 0.000(2) 0.015(2) 0.002(2) N1 0.039(3) 0.031(3) 0.025(3) -0.003(2) 0.008(2) 0.003(2) C1 0.060(5) 0.033(4) 0.021(3) -0.006(3) 0.017(3) 0.000(3) C13 0.037(4) 0.040(4) 0.034(4) -0.005(3) 0.012(3) 0.003(3) C12 0.025(4) 0.037(4) 0.019(3) -0.007(3) 0.002(3) 0.001(3) C5 0.040(4) 0.039(4) 0.024(4) 0.010(3) 0.001(3) -0.003(3) C11 0.024(4) 0.032(3) 0.020(3) -0.002(3) -0.001(3) -0.001(3) C7 0.042(4) 0.036(4) 0.038(4) 0.005(4) 0.007(3) 0.006(3) C9 0.054(5) 0.035(4) 0.033(4) -0.006(3) -0.003(3) 0.004(3) C10 0.036(4) 0.038(4) 0.030(4) -0.002(3) -0.005(3) 0.004(3) C25 0.039(4) 0.027(3) 0.037(4) -0.009(3) 0.001(3) -0.002(3) C21 0.044(5) 0.036(4) 0.026(4) -0.003(3) -0.003(3) -0.004(3) C8 0.063(5) 0.023(3) 0.043(4) -0.001(3) 0.002(4) 0.006(3) C2 0.054(5) 0.048(4) 0.015(3) -0.008(3) 0.000(3) 0.011(3) C19 0.034(4) 0.059(5) 0.043(4) -0.007(4) -0.005(3) -0.007(4) C6 0.031(4) 0.034(4) 0.028(4) -0.006(3) -0.002(3) 0.000(3) O9 0.032(2) 0.026(2) 0.024(2) -0.0075(19) 0.0044(18) 0.0038(18) O8 0.021(2) 0.031(2) 0.042(3) -0.009(2) 0.0034(18) -0.0060(19) N7 0.028(3) 0.021(3) 0.020(3) 0.000(2) 0.004(2) 0.000(2) C26 0.036(4) 0.030(3) 0.030(4) 0.002(3) 0.008(3) -0.003(3) C30 0.035(4) 0.016(3) 0.023(3) 0.005(3) -0.001(3) -0.001(3) C36 0.032(4) 0.035(4) 0.016(3) 0.001(3) 0.002(3) -0.002(3) C35 0.027(4) 0.030(3) 0.020(3) 0.007(3) 0.001(3) -0.003(3) C34 0.032(4) 0.031(3) 0.030(4) -0.001(3) 0.004(3) -0.002(3) C28 0.035(4) 0.018(3) 0.019(3) 0.001(3) 0.003(3) -0.001(3) C20 0.051(5) 0.059(5) 0.033(4) -0.001(4) -0.015(4) -0.010(4) N6 0.032(3) 0.021(3) 0.033(3) -0.005(2) 0.002(2) -0.001(2) C32 0.030(4) 0.038(4) 0.055(5) -0.007(4) -0.006(3) -0.012(3) C31 0.043(4) 0.032(4) 0.031(4) -0.003(3) 0.000(3) -0.005(3) C33 0.036(4) 0.047(4) 0.045(4) 0.005(4) 0.004(3) -0.001(3) O7 0.034(3) 0.023(2) 0.039(3) -0.009(2) 0.0075(19) -0.0009(19) C27 0.031(4) 0.032(4) 0.017(3) 0.006(3) 0.002(3) 0.003(3) O11 0.057(4) 0.056(3) 0.073(4) 0.015(3) 0.007(3) 0.004(3) C29 0.033(4) 0.024(3) 0.024(3) -0.007(3) 0.006(3) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ce1 O5 2.426(4) . y Ce1 O2 2.432(4) . y Ce1 O8 2.445(4) . y Ce1 O6 2.445(4) . y Ce1 O9 2.450(4) . y Ce1 O3 2.468(4) . y Ce1 O7 2.478(4) 4_566 y Ce1 O10 2.573(4) . y O5 N5 1.370(6) . ? O2 N3 1.350(5) . ? O3 C12 1.273(6) . ? O6 C24 1.279(7) . ? C23 C18 1.387(8) . ? C23 C22 1.407(8) . ? C23 C24 1.416(7) . ? N5 C24 1.345(7) . ? N5 C16 1.384(7) . ? O4 C15 1.207(7) . ? N4 C15 1.336(7) . ? N4 C14 1.455(7) . ? N3 C12 1.368(7) . ? N3 C4 1.397(7) . ? C15 C16 1.521(8) . ? N2 C3 1.309(7) . ? N2 C2 1.456(7) . ? C14 C13 1.513(8) . ? C4 C5 1.358(8) . ? C4 C3 1.507(8) . ? C17 C16 1.359(8) . ? C17 C18 1.422(9) . ? C22 C21 1.376(8) . ? C18 C19 1.395(8) . ? C3 O1 1.265(6) . ? N1 C25 1.466(7) . ? N1 C13 1.468(7) . ? N1 C1 1.483(7) . ? C1 C2 1.507(8) . ? C12 C11 1.430(8) . ? C5 C6 1.427(8) . ? C11 C10 1.387(8) . ? C11 C6 1.391(8) . ? C7 C8 1.363(8) . ? C7 C6 1.387(8) . ? C9 C8 1.372(9) . ? C9 C10 1.371(8) . ? C25 C26 1.490(8) . ? C21 C20 1.373(9) . ? C19 C20 1.365(9) . ? O9 C36 1.262(6) . ? O8 N7 1.356(5) . ? N7 C36 1.376(7) . ? N7 C28 1.391(7) . ? C26 N6 1.438(7) . ? C30 C35 1.393(7) . ? C30 C31 1.402(8) . ? C30 C29 1.415(8) . ? C36 C35 1.441(8) . ? C35 C34 1.392(8) . ? C34 C33 1.356(8) . ? C28 C29 1.363(8) . ? C28 C27 1.513(8) . ? N6 C27 1.322(7) . ? C32 C31 1.338(9) . ? C32 C33 1.405(9) . ? O7 C27 1.231(6) . ? O7 Ce1 2.478(4) 4_565 ? 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 O5 Ce1 O2 80.17(13) . . y O5 Ce1 O8 78.01(12) . . y O2 Ce1 O8 72.43(12) . . y O5 Ce1 O6 63.27(13) . . y O2 Ce1 O6 119.70(13) . . y O8 Ce1 O6 134.55(13) . . y O5 Ce1 O9 140.92(12) . . y O2 Ce1 O9 93.49(13) . . y O8 Ce1 O9 63.44(12) . . y O6 Ce1 O9 144.72(13) . . y O5 Ce1 O3 105.73(14) . . y O2 Ce1 O3 63.05(12) . . y O8 Ce1 O3 133.51(12) . . y O6 Ce1 O3 82.01(13) . . y O9 Ce1 O3 105.37(12) . . y O5 Ce1 O7 87.10(13) . 4_566 y O2 Ce1 O7 148.08(13) . 4_566 y O8 Ce1 O7 76.36(13) . 4_566 y O6 Ce1 O7 78.72(13) . 4_566 y O9 Ce1 O7 78.22(12) . 4_566 y O3 Ce1 O7 148.85(13) . 4_566 y O5 Ce1 O10 133.25(12) . . y O2 Ce1 O10 133.05(13) . . y O8 Ce1 O10 135.97(12) . . y O6 Ce1 O10 70.77(13) . . y O9 Ce1 O10 77.92(12) . . y O3 Ce1 O10 74.84(12) . . y O7 Ce1 O10 75.80(12) 4_566 . y N5 O5 Ce1 120.0(3) . . ? N3 O2 Ce1 119.9(3) . . ? C12 O3 Ce1 121.5(3) . . ? C24 O6 Ce1 122.0(3) . . ? C18 C23 C22 119.1(5) . . ? C18 C23 C24 120.6(6) . . ? C22 C23 C24 120.2(6) . . ? C24 N5 O5 116.4(5) . . ? C24 N5 C16 123.3(5) . . ? O5 N5 C16 120.3(5) . . ? O6 C24 N5 117.9(5) . . ? O6 C24 C23 124.1(5) . . ? N5 C24 C23 118.0(6) . . ? C15 N4 C14 121.3(5) . . ? O2 N3 C12 116.9(5) . . ? O2 N3 C4 120.3(5) . . ? C12 N3 C4 122.8(5) . . ? O4 C15 N4 124.5(6) . . ? O4 C15 C16 118.0(6) . . ? N4 C15 C16 117.3(6) . . ? C3 N2 C2 123.7(5) . . ? N4 C14 C13 114.3(5) . . ? C5 C4 N3 119.0(5) . . ? C5 C4 C3 119.7(5) . . ? N3 C4 C3 121.3(5) . . ? C16 C17 C18 121.0(6) . . ? C17 C16 N5 118.6(6) . . ? C17 C16 C15 117.5(6) . . ? N5 C16 C15 123.3(5) . . ? C21 C22 C23 119.9(6) . . ? C23 C18 C19 120.2(6) . . ? C23 C18 C17 118.0(5) . . ? C19 C18 C17 121.7(6) . . ? O1 C3 N2 124.2(6) . . ? O1 C3 C4 116.9(6) . . ? N2 C3 C4 118.9(5) . . ? C25 N1 C13 110.1(5) . . ? C25 N1 C1 110.7(4) . . ? C13 N1 C1 110.0(5) . . ? N1 C1 C2 112.4(5) . . ? N1 C13 C14 113.9(5) . . ? O3 C12 N3 117.2(5) . . ? O3 C12 C11 124.9(5) . . ? N3 C12 C11 117.9(5) . . ? C4 C5 C6 121.3(6) . . ? C10 C11 C6 119.7(5) . . ? C10 C11 C12 119.8(5) . . ? C6 C11 C12 120.5(5) . . ? C8 C7 C6 119.8(6) . . ? C8 C9 C10 120.8(6) . . ? C9 C10 C11 119.3(6) . . ? N1 C25 C26 111.6(5) . . ? C20 C21 C22 119.7(6) . . ? C7 C8 C9 120.5(6) . . ? N2 C2 C1 112.3(5) . . ? C20 C19 C18 119.2(7) . . ? C7 C6 C11 119.7(6) . . ? C7 C6 C5 121.9(6) . . ? C11 C6 C5 118.4(5) . . ? C36 O9 Ce1 122.3(4) . . ? N7 O8 Ce1 119.8(3) . . ? O8 N7 C36 116.2(4) . . ? O8 N7 C28 120.6(4) . . ? C36 N7 C28 123.2(5) . . ? N6 C26 C25 112.8(5) . . ? C35 C30 C31 118.7(6) . . ? C35 C30 C29 118.3(5) . . ? C31 C30 C29 123.0(5) . . ? O9 C36 N7 118.3(5) . . ? O9 C36 C35 124.7(6) . . ? N7 C36 C35 117.0(5) . . ? C34 C35 C30 119.5(5) . . ? C34 C35 C36 119.7(5) . . ? C30 C35 C36 120.8(5) . . ? C33 C34 C35 120.3(6) . . ? C29 C28 N7 118.8(5) . . ? C29 C28 C27 118.8(5) . . ? N7 C28 C27 122.4(5) . . ? C19 C20 C21 121.8(6) . . ? C27 N6 C26 122.8(5) . . ? C31 C32 C33 119.6(6) . . ? C32 C31 C30 121.5(6) . . ? C34 C33 C32 120.4(6) . . ? C27 O7 Ce1 163.7(4) . 4_565 ? O7 C27 N6 123.0(6) . . ? O7 C27 C28 118.3(5) . . ? N6 C27 C28 118.7(5) . . ? C28 C29 C30 121.8(5) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.076 _refine_diff_density_min -0.677 _refine_diff_density_rms 0.122 #===END data_5-Nitro-isocoumarin-3-carboxylic acid methyl ester _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-Nitro-isocoumarin-3-carboxylic acid methyl ester ; _chemical_name_common ? _chemical_melting_point 444 _chemical_formula_moiety 'C11 H7 N O6' _chemical_formula_sum 'C11 H7 N O6' _chemical_formula_weight 249.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.473(2) _cell_length_b 7.939(3) _cell_length_c 10.195(3) _cell_angle_alpha 73.012(5) _cell_angle_beta 69.945(5) _cell_angle_gamma 68.208(4) _cell_volume 518.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 155(2) _cell_measurement_reflns_used 774 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 23.87 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details 'SADABS (Bruker 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 155(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 'Siemens SMART CCD' _diffrn_measurement_method '\w-scan' _diffrn_detector_area_resol_mean 83.23 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3350 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.31 _reflns_number_total 2037 _reflns_number_gt 1452 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.059 (Bruker)' _computing_cell_refinement 'SAINT V7.07B (Bruker)' _computing_data_reduction 'SAINT V7.07B (Bruker)' _computing_structure_solution 'SIR-92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0863P)^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 2037 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1321 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.002 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 O1 O 0.3916(2) 0.13994(19) 0.37038(15) 0.0268(4) Uani 1 1 d . . . O2 O 0.4630(2) 0.4028(2) 0.27940(16) 0.0375(4) Uani 1 1 d . . . O3 O 0.8231(2) -0.2804(2) -0.13443(15) 0.0299(4) Uani 1 1 d . . . O4 O 0.8185(2) -0.37827(19) 0.08822(15) 0.0299(4) Uani 1 1 d . . . O5 O 0.1762(2) -0.0533(2) 0.58480(14) 0.0359(4) Uani 1 1 d . . . C5 C 0.6168(3) 0.1762(3) 0.1328(2) 0.0227(5) Uani 1 1 d . . . C9 C 0.7641(3) -0.0644(3) -0.0015(2) 0.0203(4) Uani 1 1 d . . . C3 C 0.5312(3) -0.1112(3) 0.2463(2) 0.0219(4) Uani 1 1 d . . . H3 H 0.5442 -0.2321 0.2457 0.026 Uiso 1 1 calc R . . N1 N 0.8047(2) -0.2553(2) -0.01687(18) 0.0220(4) Uani 1 1 d . . . O6 O 0.2870(2) -0.2816(2) 0.46100(15) 0.0338(4) Uani 1 1 d . . . C2 C 0.4100(3) -0.0333(3) 0.3580(2) 0.0227(5) Uani 1 1 d . . . C4 C 0.6418(3) -0.0069(3) 0.1266(2) 0.0196(4) Uani 1 1 d . . . C8 C 0.8484(3) 0.0488(3) -0.1171(2) 0.0231(5) Uani 1 1 d . . . H8 H 0.9239 0.0059 -0.2012 0.028 Uiso 1 1 calc R . . C1 C 0.4888(3) 0.2518(3) 0.2616(2) 0.0266(5) Uani 1 1 d . . . C10 C 0.2782(3) -0.1214(3) 0.4815(2) 0.0266(5) Uani 1 1 d . . . C7 C 0.8192(3) 0.2286(3) -0.1069(2) 0.0268(5) Uani 1 1 d . . . H7 H 0.8762 0.3067 -0.1839 0.032 Uiso 1 1 calc R . . C11 C 0.1671(3) -0.3856(3) 0.5739(2) 0.0405(6) Uani 1 1 d . . . H11A H 0.1859 -0.4988 0.5476 0.061 Uiso 1 1 calc R . . H11B H 0.0287 -0.3140 0.5894 0.061 Uiso 1 1 calc R . . H11C H 0.2071 -0.4128 0.6597 0.061 Uiso 1 1 calc R . . C6 C 0.7057(3) 0.2900(3) 0.0178(2) 0.0273(5) Uani 1 1 d . . . H6 H 0.6882 0.4095 0.0252 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0331(8) 0.0257(8) 0.0236(8) -0.0149(6) -0.0042(6) -0.0062(6) O2 0.0498(9) 0.0266(8) 0.0410(10) -0.0194(7) -0.0109(7) -0.0078(7) O3 0.0351(8) 0.0347(8) 0.0247(8) -0.0189(7) -0.0072(6) -0.0060(6) O4 0.0393(9) 0.0214(7) 0.0251(8) -0.0074(6) -0.0005(6) -0.0099(6) O5 0.0388(8) 0.0429(9) 0.0228(9) -0.0184(7) 0.0020(7) -0.0086(7) C5 0.0258(10) 0.0210(10) 0.0256(12) -0.0096(8) -0.0093(8) -0.0056(8) C9 0.0220(9) 0.0204(10) 0.0216(11) -0.0083(8) -0.0052(8) -0.0070(8) C3 0.0256(9) 0.0191(10) 0.0213(11) -0.0082(8) -0.0068(8) -0.0032(8) N1 0.0215(8) 0.0240(9) 0.0220(10) -0.0132(7) -0.0004(7) -0.0065(7) O6 0.0433(9) 0.0310(8) 0.0241(8) -0.0104(6) 0.0057(7) -0.0174(7) C2 0.0272(10) 0.0227(10) 0.0202(11) -0.0104(8) -0.0066(8) -0.0047(8) C4 0.0216(9) 0.0197(10) 0.0202(11) -0.0078(8) -0.0072(8) -0.0045(7) C8 0.0232(9) 0.0275(11) 0.0208(11) -0.0081(9) -0.0055(8) -0.0075(8) C1 0.0310(11) 0.0244(11) 0.0279(12) -0.0112(9) -0.0099(9) -0.0054(8) C10 0.0284(10) 0.0302(11) 0.0195(11) -0.0103(9) -0.0046(9) -0.0040(9) C7 0.0284(10) 0.0254(11) 0.0277(12) -0.0008(9) -0.0071(9) -0.0127(8) C11 0.0446(13) 0.0397(13) 0.0327(14) -0.0083(11) 0.0051(11) -0.0206(11) C6 0.0310(11) 0.0204(10) 0.0358(13) -0.0082(9) -0.0116(9) -0.0090(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 O1 C2 1.370(2) . ? O1 C1 1.377(2) . ? O2 C1 1.200(2) . ? O3 N1 1.225(2) . ? O4 N1 1.225(2) . ? O5 C10 1.208(2) . ? C5 C6 1.388(3) . ? C5 C4 1.412(3) . ? C5 C1 1.473(3) . ? C9 C8 1.374(3) . ? C9 C4 1.403(3) . ? C9 N1 1.476(2) . ? C3 C2 1.337(3) . ? C3 C4 1.444(3) . ? O6 C10 1.323(2) . ? O6 C11 1.448(2) . ? C2 C10 1.480(3) . ? C8 C7 1.391(3) . ? C7 C6 1.374(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 O1 C1 121.20(15) . . ? C6 C5 C4 121.33(18) . . ? C6 C5 C1 118.65(18) . . ? C4 C5 C1 120.00(18) . . ? C8 C9 C4 123.57(18) . . ? C8 C9 N1 116.82(17) . . ? C4 C9 N1 119.60(16) . . ? C2 C3 C4 119.75(18) . . ? O4 N1 O3 124.28(17) . . ? O4 N1 C9 118.06(16) . . ? O3 N1 C9 117.66(16) . . ? C10 O6 C11 116.88(16) . . ? C3 C2 O1 123.56(18) . . ? C3 C2 C10 124.54(19) . . ? O1 C2 C10 111.89(16) . . ? C9 C4 C5 115.47(17) . . ? C9 C4 C3 126.51(17) . . ? C5 C4 C3 117.88(17) . . ? C9 C8 C7 119.11(18) . . ? O2 C1 O1 117.36(18) . . ? O2 C1 C5 125.22(19) . . ? O1 C1 C5 117.42(17) . . ? O5 C10 O6 125.64(19) . . ? O5 C10 C2 123.94(19) . . ? O6 C10 C2 110.41(16) . . ? C6 C7 C8 119.60(19) . . ? C7 C6 C5 120.86(19) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 26.31 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.258 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.068