data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Miao Du' _publ_contact_author_email dumiao@public.tpt.tj.cn loop_ _publ_author_name 'Shaoming Fang' 'Min Hu' 'Li-Ran Jia' 'Cong Wang' 'Qiang Zhang' 'Song-Tao Ma' 'Miao Du' 'Chun-Sen Liu' data_1 _database_code_depnum_ccdc_archive 'CCDC 778311' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H11 La2 N3 O13' _chemical_formula_weight 755.12 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' La La -0.2871 2.4523 '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 Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 6.6641(2) _cell_length_b 7.7528(3) _cell_length_c 19.6619(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.750(3) _cell_angle_gamma 90.00 _cell_volume 956.08(6) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 1968 _cell_measurement_theta_min 3.0515 _cell_measurement_theta_max 28.2189 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 4.496 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3658 _exptl_absorpt_correction_T_max 0.4983 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 3328 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0614 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1683 _reflns_number_gt 1256 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL and PLATON (Spek, 2009)' _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. The water molecule is disordered over two sites (O7 and O7') and therefore the "EADP" restraint was applied to their thermal parameters. Standard geometry constraint was used for the water molecule (O7) in order to improve the refinement stability, which was also refined using the pseudo-isotropic "ISOR" restraint. These restraints result in the slightly lower data / parameter ratio of 9.73. ; _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^)+(0.0000P)^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 1683 _refine_ls_number_parameters 173 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0312 _refine_ls_wR_factor_gt 0.0304 _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_restrained_S_all 0.881 _refine_ls_shift/su_max 0.003 _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 O7 O 0.028(9) 0.897(16) 0.780(3) 0.025(2) Uani 0.05(2) 1 d PDU . 1 H1W H -0.0611 0.9496 0.7952 0.037 Uiso 0.05(2) 1 d PR . 1 H2W H -0.0182 0.7983 0.7859 0.037 Uiso 0.05(2) 1 d PR . 1 O7' O -0.023(2) 0.9006(15) 0.7397(11) 0.025(2) Uani 0.45(2) 1 d P . 2 H3W H -0.0613 0.9532 0.7711 0.037 Uiso 0.45(2) 1 d PR . 2 H4W H -0.0170 0.8015 0.7587 0.037 Uiso 0.45(2) 1 d PR . 2 La1 La 0.33165(4) 0.89581(4) 0.894099(14) 0.01316(7) Uani 1 1 d D . . O1 O 0.6965(4) 0.7799(4) 0.92879(17) 0.0250(9) Uani 1 1 d . . . O2 O 0.9980(4) 0.7725(4) 0.90460(16) 0.0203(8) Uani 1 1 d . . . O3 O 0.5878(4) 0.1386(4) 0.97207(13) 0.0167(8) Uani 1 1 d . . . O4 O 1.1110(4) 0.1421(4) 0.87286(16) 0.0268(9) Uani 1 1 d . . . O5 O 0.4526(5) 1.0117(4) 0.79847(16) 0.0275(8) Uani 1 1 d . . . O6 O 0.2891(4) 1.6410(4) 0.82000(15) 0.0282(9) Uani 1 1 d . . . N1 N 0.8461(5) 0.1579(5) 0.92138(16) 0.0172(10) Uani 1 1 d . . . H1A H 0.8485 0.0471 0.9231 0.021 Uiso 1 1 calc R . . N2 N 0.5000 1.6283(8) 0.7500 0.0198(14) Uani 1 2 d S . . H2A H 0.5000 1.7393 0.7500 0.024 Uiso 1 2 calc SR . . C1 C 0.8454(7) 0.7020(7) 0.9168(2) 0.0149(12) Uani 1 1 d . . . C2 C 0.8410(7) 0.5045(6) 0.9174(2) 0.0131(11) Uani 1 1 d . . . C3 C 0.9806(6) 0.4171(7) 0.8918(2) 0.0199(12) Uani 1 1 d . . . H3A H 1.0714 0.4780 0.8736 0.024 Uiso 1 1 calc R . . C4 C 0.9861(6) 0.2366(6) 0.8933(2) 0.0165(11) Uani 1 1 d . . . C5 C 0.7040(6) 0.2390(6) 0.9468(2) 0.0149(11) Uani 1 1 d . . . C6 C 0.7003(6) 0.4144(7) 0.9442(2) 0.0183(11) Uani 1 1 d . . . H6A H 0.6045 0.4750 0.9603 0.022 Uiso 1 1 calc R . . C7 C 0.5000 1.0876(10) 0.7500 0.0177(15) Uani 1 2 d S . . C8 C 0.5000 1.2812(9) 0.7500 0.0132(15) Uani 1 2 d S . . C9 C 0.3800(6) 1.3684(6) 0.7848(2) 0.0168(11) Uani 1 1 d . . . H9A H 0.2983 1.3072 0.8067 0.020 Uiso 1 1 calc R . . C10 C 0.3831(6) 1.5463(6) 0.7866(2) 0.0173(11) 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 O7 0.025(2) 0.023(2) 0.025(2) 0.0000(11) 0.0075(12) 0.0000(10) O7' 0.025(2) 0.023(2) 0.025(2) 0.0000(11) 0.0075(12) 0.0000(10) La1 0.01597(12) 0.00818(12) 0.01888(13) -0.00025(19) 0.01054(10) 0.00001(18) O1 0.0229(19) 0.014(2) 0.042(2) -0.0008(18) 0.0154(18) 0.0048(16) O2 0.0205(18) 0.0093(19) 0.035(2) 0.0012(17) 0.0142(17) -0.0046(15) O3 0.0166(15) 0.018(2) 0.0206(16) 0.0034(16) 0.0128(14) -0.0053(14) O4 0.0296(17) 0.012(2) 0.049(2) -0.0001(18) 0.0258(17) 0.0080(15) O5 0.049(2) 0.0130(19) 0.0327(19) 0.0033(18) 0.0297(17) -0.0027(17) O6 0.0376(19) 0.018(2) 0.040(2) -0.0115(18) 0.0281(18) -0.0048(16) N1 0.024(2) 0.007(2) 0.023(2) -0.0004(17) 0.0106(19) -0.0009(18) N2 0.024(3) 0.012(4) 0.024(3) 0.000 0.010(3) 0.000 C1 0.011(3) 0.013(3) 0.015(3) -0.001(2) -0.003(3) 0.000(2) C2 0.015(2) 0.010(3) 0.014(3) 0.003(2) 0.005(2) 0.000(2) C3 0.022(2) 0.015(3) 0.030(3) -0.009(3) 0.018(2) -0.004(3) C4 0.019(3) 0.013(3) 0.021(3) -0.001(2) 0.010(2) -0.002(2) C5 0.010(2) 0.020(3) 0.014(3) -0.002(2) 0.003(2) 0.002(2) C6 0.017(2) 0.018(3) 0.027(3) -0.006(3) 0.016(2) 0.001(3) C7 0.018(3) 0.016(4) 0.016(3) 0.000 0.003(3) 0.000 C8 0.013(3) 0.014(4) 0.012(3) 0.000 0.003(3) 0.000 C9 0.021(2) 0.013(3) 0.020(2) -0.003(2) 0.011(2) -0.002(2) C10 0.019(2) 0.019(3) 0.018(3) -0.002(2) 0.010(2) 0.000(2) _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 O7 O7 1.12(10) 2_556 ? O7 La1 2.4600(11) . ? O7 H1W 0.8501 . ? O7 H2W 0.8500 . ? O7 H3W 0.7079 . ? O7 H4W 0.8576 . ? O7' O7' 0.42(4) 2_556 ? O7' La1 2.739(19) 2_556 ? O7' H1W 1.2613 . ? O7' H2W 1.1990 . ? O7' H3W 0.8499 . ? O7' H4W 0.8499 . ? La1 O4 2.360(3) 1_465 ? La1 O6 2.414(3) 1_545 ? La1 O5 2.453(3) . ? La1 O1 2.463(3) . ? La1 O2 2.492(3) 1_455 ? La1 O3 2.516(3) 3_667 ? La1 O3 2.653(3) 1_565 ? La1 O7' 2.739(19) 2_556 ? La1 H2W 2.6804 . ? O1 C1 1.250(5) . ? O2 C1 1.247(5) . ? O2 La1 2.492(3) 1_655 ? O3 C5 1.308(5) . ? O3 La1 2.516(3) 3_667 ? O3 La1 2.653(3) 1_545 ? O4 C4 1.271(5) . ? O4 La1 2.360(3) 1_645 ? O5 C7 1.248(4) . ? O6 C10 1.282(5) . ? O6 La1 2.414(3) 1_565 ? N1 C5 1.365(5) . ? N1 C4 1.377(5) . ? N1 H1A 0.8600 . ? N2 C10 1.381(5) . ? N2 C10 1.381(5) 2_656 ? N2 H2A 0.8600 . ? C1 C2 1.531(5) . ? C2 C3 1.375(6) . ? C2 C6 1.408(6) . ? C3 C4 1.400(7) . ? C3 H3A 0.9300 . ? C5 C6 1.361(7) . ? C6 H6A 0.9300 . ? C7 O5 1.248(4) 2_656 ? C7 C8 1.501(9) . ? C8 C9 1.391(5) . ? C8 C9 1.391(5) 2_656 ? C9 C10 1.380(6) . ? C9 H9A 0.9300 . ? 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 O7 O7 La1 148(10) 2_556 . ? O7 O7 H1W 110.3 2_556 . ? La1 O7 H1W 98.2 . . ? O7 O7 H2W 97.7 2_556 . ? La1 O7 H2W 95.6 . . ? H1W O7 H2W 93.2 . . ? O7 O7 H3W 77.4 2_556 . ? La1 O7 H3W 126.5 . . ? H2W O7 H3W 105.9 . . ? O7 O7 H4W 62.7 2_556 . ? La1 O7 H4W 119.1 . . ? H1W O7 H4W 114.4 . . ? H3W O7 H4W 106.3 . . ? O7' O7' La1 178(4) 2_556 2_556 ? O7' O7' H1W 56.3 2_556 . ? La1 O7' H1W 121.9 2_556 . ? O7' O7' H2W 55.6 2_556 . ? La1 O7' H2W 122.4 2_556 . ? H1W O7' H2W 60.2 . . ? O7' O7' H3W 65.6 2_556 . ? La1 O7' H3W 113.0 2_556 . ? H2W O7' H3W 72.7 . . ? O7' O7' H4W 70.1 2_556 . ? La1 O7' H4W 108.5 2_556 . ? H1W O7' H4W 83.2 . . ? H3W O7' H4W 95.3 . . ? O4 La1 O6 128.05(10) 1_465 1_545 ? O4 La1 O5 85.09(9) 1_465 . ? O6 La1 O5 80.74(10) 1_545 . ? O4 La1 O7 64(3) 1_465 . ? O6 La1 O7 64(3) 1_545 . ? O5 La1 O7 71(2) . . ? O4 La1 O1 147.39(11) 1_465 . ? O6 La1 O1 76.83(10) 1_545 . ? O5 La1 O1 78.26(10) . . ? O7 La1 O1 133(2) . . ? O4 La1 O2 78.74(10) 1_465 1_455 ? O6 La1 O2 79.05(10) 1_545 1_455 ? O5 La1 O2 137.52(10) . 1_455 ? O7 La1 O2 66(2) . 1_455 ? O1 La1 O2 131.47(10) . 1_455 ? O4 La1 O3 99.84(9) 1_465 3_667 ? O6 La1 O3 118.98(9) 1_545 3_667 ? O5 La1 O3 146.25(9) . 3_667 ? O7 La1 O3 141(2) . 3_667 ? O1 La1 O3 80.21(9) . 3_667 ? O2 La1 O3 75.73(9) 1_455 3_667 ? O4 La1 O3 76.65(9) 1_465 1_565 ? O6 La1 O3 148.30(8) 1_545 1_565 ? O5 La1 O3 82.47(9) . 1_565 ? O7 La1 O3 134(3) . 1_565 ? O1 La1 O3 73.53(9) . 1_565 ? O2 La1 O3 129.95(8) 1_455 1_565 ? O3 La1 O3 66.60(10) 3_667 1_565 ? O4 La1 O7' 66.3(3) 1_465 2_556 ? O6 La1 O7' 62.3(3) 1_545 2_556 ? O5 La1 O7' 66.1(3) . 2_556 ? O7 La1 O7' 6(2) . 2_556 ? O1 La1 O7' 128.5(3) . 2_556 ? O2 La1 O7' 71.5(3) 1_455 2_556 ? O3 La1 O7' 146.2(3) 3_667 2_556 ? O3 La1 O7' 132.3(3) 1_565 2_556 ? O4 La1 H2W 76.4 1_465 . ? O6 La1 H2W 52.9 1_545 . ? O5 La1 H2W 85.3 . . ? O7 La1 H2W 18.4 . . ? O1 La1 H2W 129.0 . . ? O2 La1 H2W 52.9 1_455 . ? O3 La1 H2W 128.4 3_667 . ? O3 La1 H2W 151.2 1_565 . ? O7' La1 H2W 21.7 2_556 . ? C1 O1 La1 153.7(3) . . ? C1 O2 La1 172.9(3) . 1_655 ? C5 O3 La1 121.1(2) . 3_667 ? C5 O3 La1 123.4(2) . 1_545 ? La1 O3 La1 113.40(10) 3_667 1_545 ? C4 O4 La1 147.8(3) . 1_645 ? C7 O5 La1 172.5(4) . . ? C10 O6 La1 143.2(3) . 1_565 ? C5 N1 C4 126.2(4) . . ? C5 N1 H1A 116.9 . . ? C4 N1 H1A 116.9 . . ? C10 N2 C10 125.1(6) . 2_656 ? C10 N2 H2A 117.4 . . ? C10 N2 H2A 117.4 2_656 . ? O2 C1 O1 125.1(5) . . ? O2 C1 C2 117.3(4) . . ? O1 C1 C2 117.6(5) . . ? C3 C2 C6 120.7(5) . . ? C3 C2 C1 118.2(5) . . ? C6 C2 C1 121.1(5) . . ? C2 C3 C4 120.1(4) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 120.0 . . ? O4 C4 N1 118.4(4) . . ? O4 C4 C3 125.8(4) . . ? N1 C4 C3 115.7(4) . . ? O3 C5 C6 127.1(4) . . ? O3 C5 N1 116.0(4) . . ? C6 C5 N1 116.9(4) . . ? C5 C6 C2 120.3(4) . . ? C5 C6 H6A 119.9 . . ? C2 C6 H6A 119.9 . . ? O5 C7 O5 123.7(7) . 2_656 ? O5 C7 C8 118.1(4) . . ? O5 C7 C8 118.1(4) 2_656 . ? C9 C8 C9 121.8(6) . 2_656 ? C9 C8 C7 119.1(3) . . ? C9 C8 C7 119.1(3) 2_656 . ? C10 C9 C8 119.5(5) . . ? C10 C9 H9A 120.3 . . ? C8 C9 H9A 120.3 . . ? O6 C10 C9 125.5(4) . . ? O6 C10 N2 117.6(4) . . ? C9 C10 N2 117.0(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O7 O7 La1 O4 117(6) 2_556 . . 1_465 ? O7 O7 La1 O6 -65(4) 2_556 . . 1_545 ? O7 O7 La1 O5 23(4) 2_556 . . . ? O7 O7 La1 O1 -29(7) 2_556 . . . ? O7 O7 La1 O2 -155(6) 2_556 . . 1_455 ? O7 O7 La1 O3 -170.3(14) 2_556 . . 3_667 ? O7 O7 La1 O3 82(5) 2_556 . . 1_565 ? O7 O7 La1 O7' 5(27) 2_556 . . 2_556 ? O4 La1 O1 C1 -112.0(7) 1_465 . . . ? O6 La1 O1 C1 32.0(7) 1_545 . . . ? O5 La1 O1 C1 -51.1(7) . . . . ? O7 La1 O1 C1 -1(4) . . . . ? O2 La1 O1 C1 94.2(7) 1_455 . . . ? O3 La1 O1 C1 155.1(7) 3_667 . . . ? O3 La1 O1 C1 -136.6(7) 1_565 . . . ? O7' La1 O1 C1 -5.1(8) 2_556 . . . ? La1 O1 C1 O2 100.2(8) . . . . ? La1 O1 C1 C2 -80.1(8) . . . . ? O2 C1 C2 C3 -11.7(7) . . . . ? O1 C1 C2 C3 168.6(4) . . . . ? O2 C1 C2 C6 167.4(4) . . . . ? O1 C1 C2 C6 -12.3(7) . . . . ? C6 C2 C3 C4 -0.9(7) . . . . ? C1 C2 C3 C4 178.2(4) . . . . ? La1 O4 C4 N1 -38.8(8) 1_645 . . . ? La1 O4 C4 C3 139.3(4) 1_645 . . . ? C5 N1 C4 O4 179.0(4) . . . . ? C5 N1 C4 C3 0.7(6) . . . . ? C2 C3 C4 O4 -178.3(4) . . . . ? C2 C3 C4 N1 -0.1(7) . . . . ? La1 O3 C5 C6 -75.5(5) 3_667 . . . ? La1 O3 C5 C6 122.3(4) 1_545 . . . ? La1 O3 C5 N1 103.4(3) 3_667 . . . ? La1 O3 C5 N1 -58.8(4) 1_545 . . . ? C4 N1 C5 O3 -179.1(4) . . . . ? C4 N1 C5 C6 -0.1(6) . . . . ? O3 C5 C6 C2 177.9(4) . . . . ? N1 C5 C6 C2 -1.0(7) . . . . ? C3 C2 C6 C5 1.5(7) . . . . ? C1 C2 C6 C5 -177.6(5) . . . . ? O5 C7 C8 C9 -22.6(3) . . . . ? O5 C7 C8 C9 157.4(3) 2_656 . . . ? O5 C7 C8 C9 157.4(3) . . . 2_656 ? O5 C7 C8 C9 -22.6(3) 2_656 . . 2_656 ? C9 C8 C9 C10 -1.6(3) 2_656 . . . ? C7 C8 C9 C10 178.4(3) . . . . ? La1 O6 C10 C9 138.7(4) 1_565 . . . ? La1 O6 C10 N2 -40.4(6) 1_565 . . . ? C8 C9 C10 O6 -176.1(3) . . . . ? C8 C9 C10 N2 3.0(6) . . . . ? C10 N2 C10 O6 177.6(4) 2_656 . . . ? C10 N2 C10 C9 -1.5(3) 2_656 . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.597 _refine_diff_density_min -0.586 _refine_diff_density_rms 0.116 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 821513' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H11 N3 O13 Sm2' _chemical_formula_weight 778.00 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' Sm Sm -0.1638 3.4418 '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 Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 6.5605(7) _cell_length_b 7.6743(8) _cell_length_c 19.351(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.709(9) _cell_angle_gamma 90.00 _cell_volume 922.79(17) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 1515 _cell_measurement_theta_min 3.0994 _cell_measurement_theta_max 26.3145 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 2.800 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 6.393 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.2676 _exptl_absorpt_correction_T_max 0.3764 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 3127 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0812 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1619 _reflns_number_gt 1147 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL and PLATON (Spek, 2009)' _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. The water molecule is disordered over two sites (O7 and O7') and therefore the "EADP" restraint was applied to their thermal parameters. Standard geometry constraint was used for the water molecule (O7) in order to improve the refinement stability, which was also refined using the pseudo-isotropic "ISOR" restraint. Moreover, the pseudo-isotropic "ISOR" restraint was applied for the organic ligands. These restraints result in the poor data / parameter ratio of 9.35. ; _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^)+(0.0211P)^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 1618 _refine_ls_number_parameters 173 _refine_ls_number_restraints 66 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0527 _refine_ls_wR_factor_gt 0.0498 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 O7 O 0.00(2) 0.903(14) 0.782(7) 0.023(4) Uani 0.08(6) 1 d PU . 1 H1W H -0.0859 0.9553 0.7972 0.034 Uiso 0.08(6) 1 d PR . 1 H2W H -0.0430 0.8040 0.7879 0.034 Uiso 0.08(6) 1 d PR . 1 O7' O -0.042(4) 0.914(3) 0.7319(17) 0.023(4) Uani 0.42(6) 1 d P . 2 H3W H -0.0806 0.9665 0.7633 0.034 Uiso 0.42(6) 1 d PR . 2 H4W H -0.0363 0.8148 0.7509 0.034 Uiso 0.42(6) 1 d PR . 2 Sm1 Sm 0.34003(6) 0.90079(5) 0.89587(2) 0.01200(11) Uani 1 1 d . . . O1 O 0.6943(8) 0.7852(7) 0.9271(3) 0.0192(13) Uani 1 1 d . . . O2 O 1.0091(8) 0.7784(6) 0.9057(3) 0.0178(13) Uani 1 1 d . . . O3 O 0.5882(7) 0.1389(6) 0.9744(3) 0.0146(12) Uani 1 1 d U . . O4 O 1.1260(8) 0.1424(6) 0.8756(3) 0.0289(15) Uani 1 1 d . . . O5 O 0.4584(9) 1.0169(6) 0.8009(3) 0.0252(14) Uani 1 1 d . . . O6 O 0.2901(8) 1.6547(6) 0.8229(3) 0.0229(14) Uani 1 1 d U . . N1 N 0.8540(9) 0.1584(8) 0.9221(3) 0.0130(15) Uani 1 1 d U . . H1A H 0.8563 0.0464 0.9236 0.016 Uiso 1 1 calc R . . N2 N 0.5000 1.6384(11) 0.7500 0.016(2) Uani 1 2 d SU . . H2A H 0.5000 1.7505 0.7500 0.020 Uiso 1 2 calc SR . . C1 C 0.8475(13) 0.7050(10) 0.9164(4) 0.0113(18) Uani 1 1 d U . . C2 C 0.8437(13) 0.5068(10) 0.9172(4) 0.0134(19) Uani 1 1 d . . . C3 C 0.9885(11) 0.4183(11) 0.8930(4) 0.0160(18) Uani 1 1 d U . . H3A H 1.0833 0.4795 0.8751 0.019 Uiso 1 1 calc R . . C4 C 0.9950(12) 0.2354(10) 0.8950(4) 0.0171(18) Uani 1 1 d . . . C5 C 0.7074(11) 0.2384(9) 0.9476(4) 0.0109(17) Uani 1 1 d U . . C6 C 0.7032(11) 0.4186(11) 0.9446(4) 0.0123(17) Uani 1 1 d U . . H6A H 0.6057 0.4802 0.9610 0.015 Uiso 1 1 calc R . . C7 C 0.5000 1.0913(17) 0.7500 0.016(2) Uani 1 2 d S . . C8 C 0.5000 1.2915(13) 0.7500 0.011(2) Uani 1 2 d S . . C9 C 0.3788(11) 1.3778(9) 0.7862(4) 0.0132(17) Uani 1 1 d U . . H9A H 0.2948 1.3165 0.8086 0.016 Uiso 1 1 calc R . . C10 C 0.3864(12) 1.5594(9) 0.7881(4) 0.0150(18) Uani 1 1 d U . . 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 O7 0.023(4) 0.023(4) 0.023(4) -0.0001(11) 0.0072(16) 0.0000(11) O7' 0.023(4) 0.023(4) 0.023(4) -0.0001(11) 0.0072(16) 0.0000(11) Sm1 0.01386(19) 0.00698(16) 0.0183(2) -0.0001(3) 0.00952(15) 0.0009(3) O1 0.019(3) 0.011(3) 0.032(4) 0.002(3) 0.014(3) 0.009(3) O2 0.018(3) 0.010(3) 0.028(3) 0.003(3) 0.012(3) 0.001(3) O3 0.015(2) 0.013(2) 0.018(2) 0.0048(18) 0.0077(19) -0.0038(19) O4 0.028(3) 0.012(3) 0.058(4) 0.007(3) 0.029(3) 0.011(3) O5 0.046(4) 0.012(3) 0.025(3) -0.001(3) 0.022(3) -0.008(3) O6 0.028(2) 0.019(2) 0.029(2) -0.0101(19) 0.019(2) -0.005(2) N1 0.014(2) 0.009(3) 0.017(3) 0.001(2) 0.006(2) -0.001(2) N2 0.018(3) 0.014(4) 0.018(3) 0.000 0.006(3) 0.000 C1 0.012(3) 0.008(3) 0.012(3) 0.001(2) 0.002(2) -0.002(3) C2 0.012(4) 0.009(4) 0.013(5) 0.002(3) -0.005(4) 0.001(4) C3 0.014(3) 0.015(3) 0.022(3) 0.004(3) 0.010(2) -0.001(3) C4 0.017(4) 0.012(4) 0.023(5) 0.004(4) 0.007(4) 0.007(4) C5 0.009(3) 0.012(3) 0.011(3) 0.000(2) 0.003(2) 0.001(2) C6 0.010(3) 0.015(3) 0.014(3) -0.002(2) 0.007(2) 0.001(3) C7 0.019(6) 0.014(5) 0.017(6) 0.000 0.008(5) 0.000 C8 0.013(6) 0.004(5) 0.012(6) 0.000 0.001(5) 0.000 C9 0.014(3) 0.013(3) 0.015(3) -0.002(2) 0.008(2) -0.003(2) C10 0.018(3) 0.015(3) 0.016(3) 0.000(2) 0.011(2) -0.001(2) _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 O7 O7 1.2(3) 2_556 ? O7 Sm1 2.57(8) . ? O7 H2W 0.8399 . ? O7 H4W 0.8901 . ? O7' O7' 0.74(4) 2_556 ? O7' Sm1 2.616(19) 2_556 ? O7' H3W 0.8345 . ? O7' H4W 0.8407 . ? Sm1 O4 2.283(5) 1_465 ? Sm1 O6 2.318(5) 1_545 ? Sm1 O1 2.377(5) . ? Sm1 O5 2.386(5) . ? Sm1 O3 2.420(5) 3_667 ? Sm1 O2 2.429(5) 1_455 ? Sm1 O3 2.591(5) 1_565 ? Sm1 O7' 2.616(19) 2_556 ? O1 C1 1.251(9) . ? O2 C1 1.274(8) . ? O2 Sm1 2.429(5) 1_655 ? O3 C5 1.312(8) . ? O3 Sm1 2.420(5) 3_667 ? O3 Sm1 2.591(5) 1_545 ? O4 C4 1.263(8) . ? O4 Sm1 2.283(5) 1_645 ? O5 C7 1.241(7) . ? O6 C10 1.288(8) . ? O6 Sm1 2.318(5) 1_565 ? N1 C4 1.339(8) . ? N1 C5 1.360(8) . ? N1 H1A 0.8600 . ? N2 C10 1.349(7) . ? N2 C10 1.349(7) 2_656 ? N2 H2A 0.8600 . ? C1 C2 1.521(9) . ? C2 C3 1.367(10) . ? C2 C6 1.380(10) . ? C3 C4 1.405(10) . ? C3 H3A 0.9300 . ? C5 C6 1.384(10) . ? C6 H6A 0.9300 . ? C7 O5 1.241(7) 2_656 ? C7 C8 1.536(14) . ? C8 C9 1.386(8) . ? C8 C9 1.386(8) 2_656 ? C9 C10 1.395(9) . ? C9 H9A 0.9300 . ? 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 O7 O7 Sm1 127(10) 2_556 . ? Sm1 O7 H1W 102.2 . . ? O7 O7 H2W 103.7 2_556 . ? Sm1 O7 H2W 97.4 . . ? Sm1 O7 H3W 136.8 . . ? H1W O7 H3W 50.3 . . ? O7 O7 H4W 53.5 2_556 . ? H2W O7 H4W 50.3 . . ? H3W O7 H4W 99.1 . . ? O7' O7' Sm1 177.7(17) 2_556 2_556 ? O7' O7' H1W 57.0 2_556 . ? Sm1 O7' H1W 123.1 2_556 . ? O7' O7' H2W 56.1 2_556 . ? Sm1 O7' H2W 122.0 2_556 . ? H1W O7' H2W 51.8 . . ? O7' O7' H3W 67.3 2_556 . ? Sm1 O7' H3W 113.4 2_556 . ? H2W O7' H3W 69.0 . . ? O7' O7' H4W 70.7 2_556 . ? Sm1 O7' H4W 107.1 2_556 . ? H1W O7' H4W 78.7 . . ? H3W O7' H4W 95.7 . . ? O4 Sm1 O6 126.7(2) 1_465 1_545 ? O4 Sm1 O1 147.57(18) 1_465 . ? O6 Sm1 O1 77.67(18) 1_545 . ? O4 Sm1 O5 84.17(17) 1_465 . ? O6 Sm1 O5 81.49(16) 1_545 . ? O1 Sm1 O5 78.57(18) . . ? O4 Sm1 O3 100.66(17) 1_465 3_667 ? O6 Sm1 O3 118.15(16) 1_545 3_667 ? O1 Sm1 O3 80.82(16) . 3_667 ? O5 Sm1 O3 147.47(18) . 3_667 ? O4 Sm1 O2 79.13(17) 1_465 1_455 ? O6 Sm1 O2 77.15(17) 1_545 1_455 ? O1 Sm1 O2 131.41(16) . 1_455 ? O5 Sm1 O2 136.47(19) . 1_455 ? O3 Sm1 O2 75.59(16) 3_667 1_455 ? O4 Sm1 O7 62(3) 1_465 . ? O6 Sm1 O7 64(3) 1_545 . ? O1 Sm1 O7 136(4) . . ? O5 Sm1 O7 75(4) . . ? O3 Sm1 O7 136(5) 3_667 . ? O2 Sm1 O7 62(4) 1_455 . ? O4 Sm1 O3 76.35(18) 1_465 1_565 ? O6 Sm1 O3 150.64(16) 1_545 1_565 ? O1 Sm1 O3 74.62(16) . 1_565 ? O5 Sm1 O3 83.67(16) . 1_565 ? O3 Sm1 O3 66.67(17) 3_667 1_565 ? O2 Sm1 O3 129.51(15) 1_455 1_565 ? O7 Sm1 O3 135(2) . 1_565 ? O4 Sm1 O7' 64.8(5) 1_465 2_556 ? O6 Sm1 O7' 62.5(4) 1_545 2_556 ? O1 Sm1 O7' 128.9(8) . 2_556 ? O5 Sm1 O7' 65.6(9) . 2_556 ? O3 Sm1 O7' 145.3(10) 3_667 2_556 ? O2 Sm1 O7' 70.9(9) 1_455 2_556 ? O7 Sm1 O7' 10(4) . 2_556 ? O3 Sm1 O7' 131.7(5) 1_565 2_556 ? C1 O1 Sm1 156.0(5) . . ? C1 O2 Sm1 174.1(5) . 1_655 ? C5 O3 Sm1 122.7(4) . 3_667 ? C5 O3 Sm1 121.4(4) . 1_545 ? Sm1 O3 Sm1 113.33(16) 3_667 1_545 ? C4 O4 Sm1 147.9(5) . 1_645 ? C7 O5 Sm1 172.4(5) . . ? C10 O6 Sm1 141.6(4) . 1_565 ? C4 N1 C5 126.9(6) . . ? C4 N1 H1A 116.5 . . ? C5 N1 H1A 116.5 . . ? C10 N2 C10 126.6(8) . 2_656 ? C10 N2 H2A 116.7 . . ? C10 N2 H2A 116.7 2_656 . ? O1 C1 O2 124.3(7) . . ? O1 C1 C2 118.3(7) . . ? O2 C1 C2 117.4(7) . . ? C3 C2 C6 120.7(7) . . ? C3 C2 C1 118.6(8) . . ? C6 C2 C1 120.6(8) . . ? C2 C3 C4 120.3(7) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? O4 C4 N1 119.3(6) . . ? O4 C4 C3 125.0(7) . . ? N1 C4 C3 115.7(7) . . ? O3 C5 N1 117.4(6) . . ? O3 C5 C6 126.3(6) . . ? N1 C5 C6 116.2(6) . . ? C2 C6 C5 120.1(7) . . ? C2 C6 H6A 120.0 . . ? C5 C6 H6A 120.0 . . ? O5 C7 O5 125.3(12) . 2_656 ? O5 C7 C8 117.4(6) . . ? O5 C7 C8 117.4(6) 2_656 . ? C9 C8 C9 122.9(9) . 2_656 ? C9 C8 C7 118.6(4) . . ? C9 C8 C7 118.6(4) 2_656 . ? C8 C9 C10 118.0(7) . . ? C8 C9 H9A 121.0 . . ? C10 C9 H9A 121.0 . . ? O6 C10 N2 118.7(6) . . ? O6 C10 C9 124.1(6) . . ? N2 C10 C9 117.1(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O7 O7 Sm1 O4 114(4) 2_556 . . 1_465 ? O7 O7 Sm1 O6 -65(2) 2_556 . . 1_545 ? O7 O7 Sm1 O1 -32(5) 2_556 . . . ? O7 O7 Sm1 O5 22.9(16) 2_556 . . . ? O7 O7 Sm1 O3 -169.7(11) 2_556 . . 3_667 ? O7 O7 Sm1 O2 -153(3) 2_556 . . 1_455 ? O7 O7 Sm1 O3 88(4) 2_556 . . 1_565 ? O7 O7 Sm1 O7' 11(14) 2_556 . . 2_556 ? O4 Sm1 O1 C1 -112.3(12) 1_465 . . . ? O6 Sm1 O1 C1 30.6(12) 1_545 . . . ? O5 Sm1 O1 C1 -53.1(12) . . . . ? O3 Sm1 O1 C1 152.2(12) 3_667 . . . ? O2 Sm1 O1 C1 90.8(12) 1_455 . . . ? O7 Sm1 O1 C1 1(5) . . . . ? O3 Sm1 O1 C1 -139.6(12) 1_565 . . . ? O7' Sm1 O1 C1 -7.9(15) 2_556 . . . ? Sm1 O1 C1 O2 103.0(12) . . . . ? Sm1 O1 C1 C2 -77.9(14) . . . . ? O1 C1 C2 C3 168.5(6) . . . . ? O2 C1 C2 C3 -12.3(11) . . . . ? O1 C1 C2 C6 -14.2(12) . . . . ? O2 C1 C2 C6 165.0(6) . . . . ? C6 C2 C3 C4 0.6(11) . . . . ? C1 C2 C3 C4 177.9(7) . . . . ? Sm1 O4 C4 N1 -35.8(14) 1_645 . . . ? Sm1 O4 C4 C3 141.9(7) 1_645 . . . ? C5 N1 C4 O4 177.8(7) . . . . ? C5 N1 C4 C3 -0.1(11) . . . . ? C2 C3 C4 O4 -178.2(7) . . . . ? C2 C3 C4 N1 -0.5(11) . . . . ? Sm1 O3 C5 N1 101.2(6) 3_667 . . . ? Sm1 O3 C5 N1 -59.3(7) 1_545 . . . ? Sm1 O3 C5 C6 -76.8(8) 3_667 . . . ? Sm1 O3 C5 C6 122.7(7) 1_545 . . . ? C4 N1 C5 O3 -177.7(7) . . . . ? C4 N1 C5 C6 0.5(10) . . . . ? C3 C2 C6 C5 -0.2(11) . . . . ? C1 C2 C6 C5 -177.4(7) . . . . ? O3 C5 C6 C2 177.7(7) . . . . ? N1 C5 C6 C2 -0.4(10) . . . . ? O5 C7 C8 C9 -24.7(4) . . . . ? O5 C7 C8 C9 155.3(4) 2_656 . . . ? O5 C7 C8 C9 155.3(4) . . . 2_656 ? O5 C7 C8 C9 -24.7(4) 2_656 . . 2_656 ? C9 C8 C9 C10 -2.3(5) 2_656 . . . ? C7 C8 C9 C10 177.7(5) . . . . ? Sm1 O6 C10 N2 -42.1(10) 1_565 . . . ? Sm1 O6 C10 C9 138.9(6) 1_565 . . . ? C10 N2 C10 O6 178.6(7) 2_656 . . . ? C10 N2 C10 C9 -2.3(5) 2_656 . . . ? C8 C9 C10 O6 -176.4(6) . . . . ? C8 C9 C10 N2 4.5(9) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.936 _refine_diff_density_min -0.799 _refine_diff_density_rms 0.176 #===END data_1' _database_code_depnum_ccdc_archive 'CCDC 832151' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H9 La2 N3 O12' _chemical_formula_weight 737.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' La La -0.2871 2.4523 '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 Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 6.6571(6) _cell_length_b 7.6931(7) _cell_length_c 19.610(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.808(8) _cell_angle_gamma 90.00 _cell_volume 950.68(16) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2374 _cell_measurement_theta_min 3.0543 _cell_measurement_theta_max 26.3147 _exptl_crystal_description block _exptl_crystal_colour 'dark yellow' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 4.515 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5320 _exptl_absorpt_correction_T_max 0.6365 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 5693 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_sigmaI/netI 0.0533 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1666 _reflns_number_gt 1345 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL and PLATON (Spek, 2009)' _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. Though the value of highest residual peak is as large as 3.91, it is very near to the central La1 ion with a distance of only 0.89 A, which cannot be properly ascribed to any actual component and may be caused by heating treatment of the crystal. ; _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^)+(0.1711P)^2^+2.3803P] 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 1666 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_ref 0.2238 _refine_ls_wR_factor_gt 0.2079 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group La1 La 0.83566(12) 0.40008(9) 0.89554(4) 0.0344(4) Uani 1 1 d . . . O1 O 0.9190(15) 0.3602(12) 1.0288(5) 0.038(2) Uani 1 1 d . . . O2 O 0.8033(16) -0.2822(12) 1.0727(6) 0.047(2) Uani 1 1 d . . . O3 O 0.4954(16) -0.2761(12) 1.0932(5) 0.046(2) Uani 1 1 d . . . O4 O 0.3970(16) 0.3591(12) 1.1330(6) 0.045(2) Uani 1 1 d . . . O5 O 0.9446(15) 0.5173(12) 0.7973(5) 0.040(2) Uani 1 1 d . . . O6 O 0.7837(17) 1.1534(13) 0.8187(6) 0.045(2) Uani 1 1 d . . . N1 N 0.6577(18) 0.3433(13) 1.0816(6) 0.036(2) Uani 1 1 d . . . H1A H 0.6574 0.4551 1.0809 0.043 Uiso 1 1 d R . . N2 N 1.0000 1.141(2) 0.7500 0.046(4) Uani 1 2 d S . . H2B H 1.0000 1.2529 0.7500 0.055 Uiso 1 2 d SR . . C1 C 0.796(2) 0.2601(16) 1.0538(7) 0.037(3) Uani 1 1 d . . . C2 C 0.797(2) 0.0830(17) 1.0564(8) 0.040(3) Uani 1 1 d . . . H2A H 0.8914 0.0204 1.0398 0.048 Uiso 1 1 calc R . . C3 C 0.657(2) -0.0040(17) 1.0836(7) 0.036(3) Uani 1 1 d . . . C4 C 0.648(2) -0.2003(17) 1.0831(8) 0.035(3) Uani 1 1 d . . . C5 C 0.515(3) 0.0821(17) 1.1101(8) 0.039(3) Uani 1 1 d . . . H5A H 0.4205 0.0210 1.1271 0.046 Uiso 1 1 calc R . . C6 C 0.519(2) 0.2635(16) 1.1106(7) 0.036(3) Uani 1 1 d . . . C7 C 1.0000 0.597(2) 0.7500 0.040(5) Uani 1 2 d S . . C8 C 1.0000 0.791(3) 0.7500 0.036(4) Uani 1 2 d S . . C9 C 0.876(2) 0.8794(17) 0.7835(8) 0.038(3) Uani 1 1 d . . . H9A H 0.7896 0.8181 0.8042 0.046 Uiso 1 1 calc R . . C10 C 0.881(3) 1.056(2) 0.7857(8) 0.045(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 La1 0.0409(6) 0.0238(6) 0.0431(6) -0.0004(3) 0.0197(4) -0.0005(3) O1 0.042(5) 0.030(4) 0.047(5) 0.005(4) 0.021(4) 0.005(4) O2 0.045(6) 0.029(5) 0.073(7) -0.003(5) 0.027(5) 0.001(4) O3 0.051(6) 0.027(5) 0.063(6) 0.002(4) 0.023(5) -0.003(4) O4 0.044(6) 0.027(4) 0.082(7) -0.001(5) 0.044(6) 0.003(4) O5 0.053(6) 0.023(4) 0.054(5) -0.001(4) 0.031(4) -0.005(4) O6 0.056(6) 0.031(5) 0.059(6) -0.010(4) 0.036(5) -0.002(4) N1 0.042(6) 0.019(5) 0.051(6) 0.005(5) 0.020(5) 0.002(4) N2 0.071(13) 0.030(8) 0.044(9) 0.000 0.029(9) 0.000 C1 0.036(7) 0.031(6) 0.046(7) 0.007(5) 0.015(6) 0.006(5) C2 0.048(8) 0.031(7) 0.042(7) 0.001(6) 0.015(6) 0.000(6) C3 0.043(7) 0.017(6) 0.045(7) 0.001(6) 0.013(5) -0.004(6) C4 0.035(7) 0.024(6) 0.049(7) -0.001(6) 0.016(5) -0.007(6) C5 0.047(8) 0.031(7) 0.043(7) 0.001(6) 0.021(6) -0.001(6) C6 0.034(7) 0.028(7) 0.051(7) 0.003(5) 0.021(6) -0.003(5) C7 0.047(12) 0.026(10) 0.046(11) 0.000 0.013(9) 0.000 C8 0.044(10) 0.031(9) 0.039(9) 0.000 0.021(8) 0.000 C9 0.045(8) 0.023(6) 0.050(8) -0.001(5) 0.020(6) -0.013(5) C10 0.057(9) 0.044(8) 0.036(7) 0.000(6) 0.018(7) -0.004(7) _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 La1 O4 2.363(10) 3_667 ? La1 O6 2.378(10) 1_545 ? La1 O5 2.439(9) . ? La1 O2 2.454(10) 3_757 ? La1 O3 2.476(10) 3_657 ? La1 O1 2.508(9) . ? La1 O1 2.590(10) 3_767 ? O1 C1 1.328(16) . ? O1 La1 2.590(10) 3_767 ? O2 C4 1.279(16) . ? O2 La1 2.454(10) 3_757 ? O3 C4 1.244(16) . ? O3 La1 2.476(10) 3_657 ? O4 C6 1.274(16) . ? O4 La1 2.363(10) 3_667 ? O5 C7 1.261(12) . ? O6 C10 1.289(19) . ? O6 La1 2.378(10) 1_565 ? N1 C1 1.372(17) . ? N1 C6 1.375(17) . ? N1 H1A 0.8600 . ? N2 C10 1.380(18) . ? N2 C10 1.380(18) 2_756 ? N2 H2B 0.8599 . ? C1 C2 1.363(17) . ? C2 C3 1.39(2) . ? C2 H2A 0.9300 . ? C3 C5 1.39(2) . ? C3 C4 1.511(19) . ? C5 C6 1.396(17) . ? C5 H5A 0.9300 . ? C7 O5 1.261(12) 2_756 ? C7 C8 1.50(2) . ? C8 C9 1.388(17) 2_756 ? C8 C9 1.388(17) . ? C9 C10 1.363(19) . ? C9 H9A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 La1 O6 121.7(4) 3_667 1_545 ? O4 La1 O5 82.1(3) 3_667 . ? O6 La1 O5 79.3(3) 1_545 . ? O4 La1 O2 149.7(3) 3_667 3_757 ? O6 La1 O2 78.2(4) 1_545 3_757 ? O5 La1 O2 79.7(3) . 3_757 ? O4 La1 O3 77.8(3) 3_667 3_657 ? O6 La1 O3 78.3(3) 1_545 3_657 ? O5 La1 O3 135.5(3) . 3_657 ? O2 La1 O3 131.5(3) 3_757 3_657 ? O4 La1 O1 104.5(3) 3_667 . ? O6 La1 O1 120.0(3) 1_545 . ? O5 La1 O1 147.7(3) . . ? O2 La1 O1 79.7(3) 3_757 . ? O3 La1 O1 76.4(3) 3_657 . ? O4 La1 O1 79.7(3) 3_667 3_767 ? O6 La1 O1 150.2(3) 1_545 3_767 ? O5 La1 O1 84.1(3) . 3_767 ? O2 La1 O1 74.5(3) 3_757 3_767 ? O3 La1 O1 129.6(3) 3_657 3_767 ? O1 La1 O1 66.6(4) . 3_767 ? C1 O1 La1 120.0(8) . . ? C1 O1 La1 123.4(8) . 3_767 ? La1 O1 La1 113.4(3) . 3_767 ? C4 O2 La1 156.3(10) . 3_757 ? C4 O3 La1 173.3(9) . 3_657 ? C6 O4 La1 144.4(9) . 3_667 ? C7 O5 La1 172.7(9) . . ? C10 O6 La1 141.8(10) . 1_565 ? C1 N1 C6 125.6(11) . . ? C1 N1 H1A 117.2 . . ? C6 N1 H1A 117.1 . . ? C10 N2 C10 123.7(19) . 2_756 ? C10 N2 H2B 118.1 . . ? C10 N2 H2B 118.1 2_756 . ? O1 C1 C2 126.8(13) . . ? O1 C1 N1 116.7(11) . . ? C2 C1 N1 116.5(13) . . ? C1 C2 C3 120.2(14) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C5 C3 C2 122.5(12) . . ? C5 C3 C4 116.8(12) . . ? C2 C3 C4 120.6(12) . . ? O3 C4 O2 122.5(12) . . ? O3 C4 C3 119.9(11) . . ? O2 C4 C3 117.5(11) . . ? C3 C5 C6 117.9(13) . . ? C3 C5 H5A 121.1 . . ? C6 C5 H5A 121.1 . . ? O4 C6 N1 118.1(11) . . ? O4 C6 C5 124.6(13) . . ? N1 C6 C5 117.2(12) . . ? O5 C7 O5 122.1(16) . 2_756 ? O5 C7 C8 118.9(8) . . ? O5 C7 C8 118.9(8) 2_756 . ? C9 C8 C9 121.6(18) 2_756 . ? C9 C8 C7 119.2(9) 2_756 . ? C9 C8 C7 119.2(9) . . ? C10 C9 C8 119.4(14) . . ? C10 C9 H9A 120.3 . . ? C8 C9 H9A 120.3 . . ? O6 C10 C9 125.7(15) . . ? O6 C10 N2 116.4(14) . . ? C9 C10 N2 117.8(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 La1 O1 C1 88.8(9) 3_667 . . . ? O6 La1 O1 C1 -52.1(9) 1_545 . . . ? O5 La1 O1 C1 -173.0(8) . . . . ? O2 La1 O1 C1 -122.0(9) 3_757 . . . ? O3 La1 O1 C1 15.5(8) 3_657 . . . ? O1 La1 O1 C1 160.6(11) 3_767 . . . ? O4 La1 O1 La1 -71.8(4) 3_667 . . 3_767 ? O6 La1 O1 La1 147.3(4) 1_545 . . 3_767 ? O5 La1 O1 La1 26.4(7) . . . 3_767 ? O2 La1 O1 La1 77.4(4) 3_757 . . 3_767 ? O3 La1 O1 La1 -145.1(4) 3_657 . . 3_767 ? O1 La1 O1 La1 0.0 3_767 . . 3_767 ? La1 O1 C1 C2 78.2(16) . . . . ? La1 O1 C1 C2 -123.3(13) 3_767 . . . ? La1 O1 C1 N1 -103.5(12) . . . . ? La1 O1 C1 N1 55.0(14) 3_767 . . . ? C6 N1 C1 O1 -179.5(12) . . . . ? O1 C1 C2 C3 -179.4(13) . . . . ? N1 C1 C2 C3 2(2) . . . . ? C1 C2 C3 C4 176.7(12) . . . . ? C5 C3 C4 O3 13.0(17) . . . . ? C2 C3 C4 O3 -164.9(14) . . . . ? C5 C3 C4 O2 -166.3(14) . . . . ? C2 C3 C4 O2 15.8(17) . . . . ? C4 C3 C5 C6 -179.5(12) . . . . ? La1 O4 C6 C5 -130.5(14) 3_667 . . . ? C1 N1 C6 O4 -178.6(13) . . . . ? C1 N1 C6 C5 -2(2) . . . . ? C3 C5 C6 O4 179.6(14) . . . . ? C3 C5 C6 N1 3(2) . . . . ? O5 C7 C8 C9 158.1(8) . . . 2_756 ? O5 C7 C8 C9 -21.9(8) 2_756 . . 2_756 ? O5 C7 C8 C9 -21.9(8) . . . . ? O5 C7 C8 C9 158.1(8) 2_756 . . . ? C9 C8 C9 C10 -2.2(10) 2_756 . . . ? C7 C8 C9 C10 177.8(10) . . . . ? La1 O6 C10 C9 135.2(15) 1_565 . . . ? La1 O6 C10 N2 -45(2) 1_565 . . . ? C8 C9 C10 O6 -175.5(12) . . . . ? C8 C9 C10 N2 4(2) . . . . ? C10 N2 C10 O6 177.6(15) 2_756 . . . ? C10 N2 C10 C9 -2.2(10) 2_756 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.912 _refine_diff_density_min -0.912 _refine_diff_density_rms 0.329 #===END data_4' _database_code_depnum_ccdc_archive 'CCDC 832152' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H9 N3 O12 Sm2' _chemical_formula_weight 760.00 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' Sm Sm -0.1638 3.4418 '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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 6.5238(2) _cell_length_b 7.6246(2) _cell_length_c 19.2614(7) _cell_angle_alpha 90.00 _cell_angle_beta 108.791(3) _cell_angle_gamma 90.00 _cell_volume 907.02(5) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 1850 _cell_measurement_theta_min 3.1168 _cell_measurement_theta_max 26.3120 _exptl_crystal_description BLOCK _exptl_crystal_colour 'dark yellow' _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 2.783 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 6.496 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95487 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 3195 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1591 _reflns_number_gt 1421 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL and PLATON (Spek, 2009)' _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. The N2 atom of the ligand was refined using the pseudo-isotropic "ISOR" restraint as well as similar U~ij~ (SIMU) restraint, as the free refinement gave unrealistic anisotropic displacement parameters. Rigid bond (DELU) restraint was also used to treat this atom. These restraints result in the slightly lower data / parameter ratio of 9.94. ; _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^)+(0.0368P)^2^+0.5270P] 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 1591 _refine_ls_number_parameters 160 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0313 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.0628 _refine_ls_wR_factor_gt 0.0604 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 Sm1 Sm 0.34220(4) -0.40329(3) -0.103309(13) 0.01384(12) Uani 1 1 d . . . C1 C 0.2950(8) -0.2588(7) 0.0532(3) 0.0166(11) Uani 1 1 d . . . C2 C 0.0105(8) -0.2649(7) 0.1086(3) 0.0170(11) Uani 1 1 d . . . C3 C 0.0115(9) -0.0808(7) 0.1104(3) 0.0184(11) Uani 1 1 d . . . H3A H -0.0820 -0.0198 0.1293 0.022 Uiso 1 1 calc R . . C4 C 0.2982(8) -0.0798(7) 0.0556(3) 0.0180(11) Uani 1 1 d . . . H4A H 0.3954 -0.0172 0.0389 0.022 Uiso 1 1 calc R . . C5 C 0.1545(7) 0.0077(7) 0.0833(3) 0.0154(10) Uani 1 1 d . . . C6 C 0.1488(8) 0.2061(7) 0.0844(3) 0.0167(11) Uani 1 1 d . . . C7 C 0.3792(9) -0.0681(7) -0.2132(3) 0.0196(12) Uani 1 1 d . . . C8 C 0.3751(9) 0.1145(7) -0.2153(3) 0.0196(12) Uani 1 1 d . . . H8A H 0.2894 0.1768 -0.1936 0.024 Uiso 1 1 calc R . . C9 C 0.5000 0.2018(10) -0.2500 0.0163(15) Uani 1 2 d S . . C10 C 0.5000 -0.5980(10) -0.2500 0.0191(16) Uani 1 2 d S . . N1 N 0.1505(7) -0.3438(6) 0.0796(2) 0.0170(9) Uani 1 1 d . . . H1A H 0.1485 -0.4565 0.0777 0.020 Uiso 1 1 d R . . N2 N 0.5000 -0.1496(8) -0.2500 0.0190(14) Uani 1 2 d SU . . H2A H 0.5000 -0.2624 -0.2500 0.023 Uiso 1 2 d SR . . O1 O 0.4162(5) -0.3610(5) 0.02668(19) 0.0183(8) Uani 1 1 d . . . O2 O -0.1160(6) -0.3613(5) 0.1308(2) 0.0242(9) Uani 1 1 d . . . O3 O -0.0112(6) 0.2813(5) 0.09383(19) 0.0228(8) Uani 1 1 d . . . O4 O 0.3037(6) 0.2868(5) 0.0736(2) 0.0244(8) Uani 1 1 d . . . O5 O 0.2831(6) -0.1642(5) -0.1786(2) 0.0249(9) Uani 1 1 d . . . O6 O 0.4453(6) -0.5215(5) -0.20141(18) 0.0230(8) 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 Sm1 0.01913(17) 0.00612(17) 0.01990(16) 0.00030(11) 0.01134(11) -0.00044(11) C1 0.017(2) 0.015(3) 0.019(2) -0.001(2) 0.007(2) 0.002(2) C2 0.019(3) 0.011(3) 0.022(2) -0.002(2) 0.008(2) -0.006(2) C3 0.021(3) 0.010(3) 0.028(3) -0.002(2) 0.013(2) 0.001(2) C4 0.022(3) 0.013(3) 0.024(3) -0.002(2) 0.014(2) -0.005(2) C5 0.017(2) 0.007(3) 0.020(2) -0.001(2) 0.0039(19) -0.004(2) C6 0.021(3) 0.012(3) 0.018(2) -0.003(2) 0.008(2) 0.000(2) C7 0.025(3) 0.017(3) 0.019(2) 0.002(2) 0.011(2) 0.001(2) C8 0.030(3) 0.013(3) 0.022(3) 0.002(2) 0.016(2) 0.002(2) C9 0.025(4) 0.006(4) 0.018(3) 0.000 0.005(3) 0.000 C10 0.026(4) 0.008(4) 0.023(4) 0.000 0.008(3) 0.000 N1 0.025(2) 0.004(2) 0.025(2) -0.0015(18) 0.0121(18) 0.0004(17) N2 0.032(3) 0.003(3) 0.027(3) 0.000 0.017(3) 0.000 O1 0.0237(19) 0.0106(19) 0.0248(18) -0.0013(15) 0.0135(15) 0.0036(15) O2 0.032(2) 0.011(2) 0.041(2) -0.0023(16) 0.0270(18) -0.0049(16) O3 0.0254(19) 0.011(2) 0.037(2) 0.0007(17) 0.0158(16) 0.0021(17) O4 0.0228(19) 0.014(2) 0.040(2) 0.0018(18) 0.0165(16) -0.0025(17) O5 0.036(2) 0.012(2) 0.034(2) 0.0080(17) 0.0233(18) 0.0033(17) O6 0.038(2) 0.0098(19) 0.0280(19) -0.0048(17) 0.0207(16) 0.0014(17) _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 Sm1 O2 2.275(4) 3_545 ? Sm1 O5 2.284(4) . ? Sm1 O4 2.367(3) 3_655 ? Sm1 O6 2.378(3) . ? Sm1 O3 2.411(3) 3 ? Sm1 O1 2.414(3) . ? Sm1 O1 2.528(3) 3_645 ? C1 O1 1.324(6) . ? C1 C4 1.366(7) . ? C1 N1 1.371(6) . ? C2 O2 1.278(6) . ? C2 N1 1.354(7) . ? C2 C3 1.404(7) . ? C3 C5 1.382(7) . ? C3 H3A 0.9300 . ? C4 C5 1.390(7) . ? C4 H4A 0.9300 . ? C5 C6 1.513(8) . ? C6 O3 1.255(6) . ? C6 O4 1.256(6) . ? C7 O5 1.281(6) . ? C7 N2 1.367(6) . ? C7 C8 1.393(7) . ? C8 C9 1.380(6) . ? C8 H8A 0.9300 . ? C9 C8 1.380(6) 2_654 ? C9 C10 1.526(10) 1_565 ? C10 O6 1.248(5) . ? C10 O6 1.248(5) 2_654 ? C10 C9 1.526(10) 1_545 ? N1 H1A 0.8599 . ? N2 C7 1.367(6) 2_654 ? N2 H2A 0.8600 . ? O1 Sm1 2.528(3) 3_645 ? O2 Sm1 2.275(4) 3_545 ? O3 Sm1 2.411(3) 3 ? O4 Sm1 2.367(3) 3_655 ? 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 O2 Sm1 O5 121.17(14) 3_545 . ? O2 Sm1 O4 149.52(13) 3_545 3_655 ? O5 Sm1 O4 78.80(13) . 3_655 ? O2 Sm1 O6 81.04(13) 3_545 . ? O5 Sm1 O6 80.26(13) . . ? O4 Sm1 O6 80.23(13) 3_655 . ? O2 Sm1 O3 78.02(13) 3_545 3 ? O5 Sm1 O3 76.60(13) . 3 ? O4 Sm1 O3 131.68(13) 3_655 3 ? O6 Sm1 O3 134.09(12) . 3 ? O2 Sm1 O1 104.19(12) 3_545 . ? O5 Sm1 O1 119.25(13) . . ? O4 Sm1 O1 81.11(12) 3_655 . ? O6 Sm1 O1 149.49(12) . . ? O3 Sm1 O1 75.81(12) 3 . ? O2 Sm1 O1 79.10(13) 3_545 3_645 ? O5 Sm1 O1 152.13(12) . 3_645 ? O4 Sm1 O1 75.49(12) 3_655 3_645 ? O6 Sm1 O1 84.94(12) . 3_645 ? O3 Sm1 O1 129.41(12) 3 3_645 ? O1 Sm1 O1 67.08(13) . 3_645 ? O1 C1 C4 126.7(5) . . ? O1 C1 N1 115.6(4) . . ? C4 C1 N1 117.7(4) . . ? O2 C2 N1 118.5(5) . . ? O2 C2 C3 124.4(5) . . ? N1 C2 C3 117.1(5) . . ? C5 C3 C2 118.5(5) . . ? C5 C3 H3A 120.7 . . ? C2 C3 H3A 120.7 . . ? C1 C4 C5 119.2(5) . . ? C1 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C3 C5 C4 122.1(5) . . ? C3 C5 C6 117.4(4) . . ? C4 C5 C6 120.5(4) . . ? O3 C6 O4 123.5(5) . . ? O3 C6 C5 118.9(4) . . ? O4 C6 C5 117.6(4) . . ? O5 C7 N2 118.0(5) . . ? O5 C7 C8 125.3(5) . . ? N2 C7 C8 116.6(5) . . ? C9 C8 C7 119.2(5) . . ? C9 C8 H8A 120.4 . . ? C7 C8 H8A 120.4 . . ? C8 C9 C8 122.3(7) 2_654 . ? C8 C9 C10 118.8(4) 2_654 1_565 ? C8 C9 C10 118.8(4) . 1_565 ? O6 C10 O6 124.3(7) . 2_654 ? O6 C10 C9 117.9(3) . 1_545 ? O6 C10 C9 117.9(3) 2_654 1_545 ? C2 N1 C1 125.4(4) . . ? C2 N1 H1A 117.3 . . ? C1 N1 H1A 117.3 . . ? C7 N2 C7 126.0(7) . 2_654 ? C7 N2 H2A 117.0 . . ? C7 N2 H2A 117.0 2_654 . ? C1 O1 Sm1 122.2(3) . . ? C1 O1 Sm1 122.1(3) . 3_645 ? Sm1 O1 Sm1 112.92(13) . 3_645 ? C2 O2 Sm1 144.7(3) . 3_545 ? C6 O3 Sm1 174.0(3) . 3 ? C6 O4 Sm1 156.7(3) . 3_655 ? C7 O5 Sm1 140.9(3) . . ? C10 O6 Sm1 174.3(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C2 C3 C5 -178.9(5) . . . . ? N1 C2 C3 C5 -0.5(7) . . . . ? O1 C1 C4 C5 178.0(5) . . . . ? N1 C1 C4 C5 -1.0(7) . . . . ? C2 C3 C5 C4 -0.9(8) . . . . ? C2 C3 C5 C6 178.7(4) . . . . ? C1 C4 C5 C3 1.7(8) . . . . ? C1 C4 C5 C6 -177.9(4) . . . . ? C3 C5 C6 O3 -15.5(6) . . . . ? C4 C5 C6 O3 164.1(5) . . . . ? C3 C5 C6 O4 166.5(5) . . . . ? C4 C5 C6 O4 -14.0(6) . . . . ? O5 C7 C8 C9 174.9(4) . . . . ? N2 C7 C8 C9 -3.6(7) . . . . ? C7 C8 C9 C8 1.9(4) . . . 2_654 ? C7 C8 C9 C10 -178.1(4) . . . 1_565 ? O2 C2 N1 C1 179.7(5) . . . . ? C3 C2 N1 C1 1.2(7) . . . . ? O1 C1 N1 C2 -179.5(4) . . . . ? C4 C1 N1 C2 -0.4(7) . . . . ? O5 C7 N2 C7 -176.8(5) . . . 2_654 ? C8 C7 N2 C7 1.8(3) . . . 2_654 ? C4 C1 O1 Sm1 -76.9(6) . . . . ? N1 C1 O1 Sm1 102.1(4) . . . . ? C4 C1 O1 Sm1 123.3(5) . . . 3_645 ? N1 C1 O1 Sm1 -57.7(5) . . . 3_645 ? O2 Sm1 O1 C1 -90.0(4) 3_545 . . . ? O5 Sm1 O1 C1 48.9(4) . . . . ? O4 Sm1 O1 C1 120.6(4) 3_655 . . . ? O6 Sm1 O1 C1 173.5(3) . . . . ? O3 Sm1 O1 C1 -16.6(3) 3 . . . ? O1 Sm1 O1 C1 -161.5(4) 3_645 . . . ? O2 Sm1 O1 Sm1 71.42(16) 3_545 . . 3_645 ? O5 Sm1 O1 Sm1 -149.68(14) . . . 3_645 ? O4 Sm1 O1 Sm1 -77.92(15) 3_655 . . 3_645 ? O6 Sm1 O1 Sm1 -25.0(3) . . . 3_645 ? O3 Sm1 O1 Sm1 144.88(17) 3 . . 3_645 ? O1 Sm1 O1 Sm1 0.0 3_645 . . 3_645 ? N1 C2 O2 Sm1 -44.5(8) . . . 3_545 ? C3 C2 O2 Sm1 133.9(5) . . . 3_545 ? O3 C6 O4 Sm1 104.0(9) . . . 3_655 ? C5 C6 O4 Sm1 -78.0(10) . . . 3_655 ? N2 C7 O5 Sm1 43.3(8) . . . . ? C8 C7 O5 Sm1 -135.2(5) . . . . ? O2 Sm1 O5 C7 -126.0(5) 3_545 . . . ? O4 Sm1 O5 C7 29.1(6) 3_655 . . . ? O6 Sm1 O5 C7 -52.8(6) . . . . ? O3 Sm1 O5 C7 167.2(6) 3 . . . ? O1 Sm1 O5 C7 102.2(6) . . . . ? O1 Sm1 O5 C7 6.2(7) 3_645 . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.630 _refine_diff_density_min -0.699 _refine_diff_density_rms 0.151 #===END