# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Michel Verdaguer' _publ_contact_author_email MICHEL.VERDAGUER@UPMC.FR _publ_section_title ; Synthesis, crystal structure and magnetic properties of two oxalato-bridged dimetallic trinuclear complexes combined with a polar cation. ; loop_ _publ_author_name 'Michel Verdaguer' 'Kamal Boubekeur' 'Rodrigue Lescouezec' 'F Lloret' 'Emilio Pardo Marin' ; E.Ruiz ; 'Cyrille Train' # Attachment 'emil16F2.cif' data_emil16 _database_code_depnum_ccdc_archive 'CCDC 762572' #TrackingRef 'emil16F2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H4 Cr2 Mn O26, 4(C5 H7 N2), 2.99(H2 O)' _chemical_formula_sum 'C32 H37.98 Cr2 Mn N8 O29' _chemical_formula_weight 1157.46 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' Cr Cr 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.5113(15) _cell_length_b 20.250(3) _cell_length_c 21.810(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.447(10) _cell_angle_gamma 90.00 _cell_volume 4999.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 195 _cell_measurement_theta_min 4.17 _cell_measurement_theta_max 23.06 _exptl_crystal_description 'hexagonal plate' _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2363.9 _exptl_absorpt_coefficient_mu 0.774 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7770 _exptl_absorpt_correction_T_max 0.8976 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _diffrn_ambient_temperature 250(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 29683 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 30.00 _reflns_number_total 7281 _reflns_number_gt 5577 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV, 1997-2000)' _computing_cell_refinement 'DIRAX/LSQ (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _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^)+(0.0887P)^2^+2.9307P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7281 _refine_ls_number_parameters 335 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1366 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 Mn1 Mn -0.2500 0.2500 0.0000 0.02580(13) Uani 1 2 d S . . Cr1 Cr 0.18439(3) 0.210457(19) 0.149438(17) 0.02320(11) Uani 1 1 d . . . O1 O -0.10561(14) 0.17492(9) 0.02133(8) 0.0286(3) Uani 1 1 d . . . O2 O -0.11887(15) 0.29874(9) 0.07297(8) 0.0301(4) Uani 1 1 d . . . O3 O 0.05885(15) 0.28005(9) 0.13280(8) 0.0289(4) Uani 1 1 d . . . O4 O 0.06922(14) 0.16022(8) 0.08560(8) 0.0260(3) Uani 1 1 d . . . O5 O 0.30652(15) 0.14046(9) 0.15405(9) 0.0326(4) Uani 1 1 d . . . O6 O 0.26913(15) 0.24714(9) 0.08559(8) 0.0286(4) Uani 1 1 d . . . O7 O 0.43267(18) 0.23185(12) 0.04493(10) 0.0424(5) Uani 1 1 d . . . O8 O 0.4712(2) 0.11538(12) 0.11759(12) 0.0545(6) Uani 1 1 d . . . O9 O 0.12379(15) 0.17070(9) 0.22045(8) 0.0299(4) Uani 1 1 d . . . O10 O 0.28184(16) 0.26321(10) 0.21582(9) 0.0331(4) Uani 1 1 d . . . O11 O 0.3257(3) 0.26951(14) 0.32029(11) 0.0617(7) Uani 1 1 d . . . O12 O 0.1575(2) 0.17241(11) 0.32540(9) 0.0437(5) Uani 1 1 d . . . O13 O -0.33475(16) 0.19677(11) 0.06494(9) 0.0360(4) Uani 1 1 d . . . H13A H -0.399(2) 0.20109(18) 0.06363(9) 0.043 Uiso 1 1 d R . . H13B H -0.3069(9) 0.2022(2) 0.0986(11) 0.043 Uiso 1 1 d R . . C1 C -0.02394(19) 0.19357(11) 0.06325(10) 0.0230(4) Uani 1 1 d . . . C2 C -0.03025(19) 0.26353(11) 0.09194(11) 0.0236(4) Uani 1 1 d . . . C3 C 0.3852(2) 0.15094(14) 0.11955(12) 0.0321(5) Uani 1 1 d . . . C4 C 0.3639(2) 0.21503(13) 0.07910(11) 0.0284(5) Uani 1 1 d . . . C5 C 0.1752(2) 0.19188(13) 0.27442(12) 0.0298(5) Uani 1 1 d . . . C6 C 0.2698(2) 0.24674(14) 0.27184(13) 0.0349(5) Uani 1 1 d . . . N1 N 0.1292(3) 0.54401(18) 0.05610(18) 0.0669(9) Uani 1 1 d . . . H1 H 0.0965 0.5804 0.0656 0.096(18) Uiso 1 1 calc R . . N2 N 0.2922(3) 0.37260(14) 0.01779(13) 0.0479(6) Uani 1 1 d . . . H2A H 0.2708 0.3352 0.0319 0.057 Uiso 1 1 calc R . . H2B H 0.3497 0.3738 -0.0032 0.057 Uiso 1 1 calc R . . C7 C 0.2165(5) 0.5463(2) 0.0226(2) 0.0749(12) Uani 1 1 d . . . H7 H 0.2394 0.5874 0.0087 0.090 Uiso 1 1 calc R . . C8 C 0.2728(4) 0.49038(18) 0.0084(2) 0.0588(9) Uani 1 1 d . . . H8 H 0.3345 0.4933 -0.0144 0.071 Uiso 1 1 calc R . . C9 C 0.2374(3) 0.42764(15) 0.02821(14) 0.0391(6) Uani 1 1 d . . . C10 C 0.1431(3) 0.42795(18) 0.06221(16) 0.0482(7) Uani 1 1 d . . . H10 H 0.1157 0.3878 0.0760 0.058 Uiso 1 1 calc R . . C11 C 0.0922(3) 0.4855(2) 0.07501(19) 0.0585(9) Uani 1 1 d . . . H11 H 0.0299 0.4846 0.0975 0.070 Uiso 1 1 calc R . . N3 N 0.4663(4) 0.5472(2) 0.17047(19) 0.0747(10) Uani 1 1 d . . . H3 H 0.4668 0.5901 0.1710 0.090 Uiso 1 1 calc R . . N4 N 0.4665(3) 0.34792(19) 0.17359(18) 0.0686(9) Uani 1 1 d . . . H4A H 0.4082 0.3268 0.1851 0.082 Uiso 1 1 calc R . . H4B H 0.5260 0.3261 0.1642 0.082 Uiso 1 1 calc R . . C12 C 0.5589(5) 0.5140(2) 0.1546(2) 0.0724(12) Uani 1 1 d . . . H12 H 0.6231 0.5378 0.1446 0.087 Uiso 1 1 calc R . . C13 C 0.5600(4) 0.4484(3) 0.1531(2) 0.0710(12) Uani 1 1 d . . . H13 H 0.6236 0.4264 0.1405 0.100(18) Uiso 1 1 calc R . . C14 C 0.4649(3) 0.4102(2) 0.17056(17) 0.0542(8) Uani 1 1 d . . . C15 C 0.3689(3) 0.4470(3) 0.18562(18) 0.0652(11) Uani 1 1 d . . . H15 H 0.3030 0.4249 0.1957 0.078 Uiso 1 1 calc R . . C16 C 0.3722(4) 0.5139(2) 0.18553(19) 0.0656(10) Uani 1 1 d . . . H16 H 0.3086 0.5378 0.1960 0.038(8) Uiso 1 1 calc R . . O14 O 0.3703(6) 0.0652(3) 0.2701(2) 0.148(2) Uani 1 1 d D . . H14A H 0.3639(6) 0.1002(6) 0.2446(4) 0.178 Uiso 1 1 d RD . . H14B H 0.4116(8) 0.0709(3) 0.3085(6) 0.178 Uiso 1 1 d RD . . O15 O 0.0000 0.394(2) 0.2500 0.247(18) Uiso 0.33 2 d SPD . . H15A H 0.0650(13) 0.372(2) 0.24435(11) 0.296 Uiso 0.33 1 d PRD . . O16 O 0.3537(14) -0.0822(8) 0.1420(7) 0.123(5) Uiso 0.33 1 d PD . . H16A H 0.3538(14) -0.0385(10) 0.1326(7) 0.147 Uiso 0.33 1 d PRD . . H16B H 0.2896(17) -0.0989(8) 0.1160(8) 0.147 Uiso 0.33 1 d PRD . . 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 Mn1 0.0186(2) 0.0319(3) 0.0267(2) 0.00225(19) 0.00366(17) 0.00101(18) Cr1 0.01779(17) 0.0271(2) 0.02478(19) 0.00217(13) 0.00403(13) 0.00035(13) O1 0.0220(7) 0.0301(9) 0.0327(8) -0.0047(7) 0.0022(6) -0.0003(6) O2 0.0249(8) 0.0301(9) 0.0338(9) -0.0036(7) 0.0009(7) 0.0062(7) O3 0.0230(7) 0.0292(9) 0.0326(9) -0.0051(7) 0.0004(6) 0.0012(6) O4 0.0217(7) 0.0256(8) 0.0303(8) -0.0009(6) 0.0037(6) 0.0034(6) O5 0.0256(8) 0.0357(10) 0.0383(9) 0.0108(7) 0.0107(7) 0.0062(7) O6 0.0246(8) 0.0317(9) 0.0304(8) 0.0079(7) 0.0078(6) 0.0034(7) O7 0.0311(9) 0.0556(13) 0.0447(11) 0.0159(9) 0.0177(8) 0.0052(9) O8 0.0467(12) 0.0529(14) 0.0710(16) 0.0190(12) 0.0300(12) 0.0248(11) O9 0.0260(8) 0.0365(10) 0.0283(8) -0.0012(7) 0.0081(6) -0.0077(7) O10 0.0299(9) 0.0374(10) 0.0310(9) 0.0036(7) 0.0025(7) -0.0104(7) O11 0.0757(17) 0.0716(17) 0.0336(11) -0.0024(11) -0.0018(11) -0.0416(14) O12 0.0539(12) 0.0488(12) 0.0301(9) 0.0021(8) 0.0123(8) -0.0156(10) O13 0.0255(8) 0.0565(13) 0.0270(8) 0.0034(8) 0.0076(7) -0.0014(8) C1 0.0211(9) 0.0240(11) 0.0253(10) 0.0005(8) 0.0077(8) -0.0011(8) C2 0.0211(9) 0.0244(11) 0.0265(10) -0.0016(8) 0.0074(8) 0.0000(8) C3 0.0270(11) 0.0349(13) 0.0352(12) 0.0043(10) 0.0079(9) 0.0051(9) C4 0.0235(10) 0.0347(13) 0.0273(11) 0.0032(9) 0.0050(8) 0.0013(9) C5 0.0287(11) 0.0322(13) 0.0295(11) -0.0003(9) 0.0081(9) -0.0037(9) C6 0.0357(13) 0.0364(14) 0.0313(12) 0.0017(10) 0.0024(10) -0.0098(11) N1 0.070(2) 0.0524(19) 0.078(2) -0.0124(16) 0.0130(18) 0.0214(16) N2 0.0605(17) 0.0381(14) 0.0481(15) 0.0023(11) 0.0178(13) 0.0095(12) C7 0.093(3) 0.040(2) 0.094(3) 0.004(2) 0.021(3) -0.005(2) C8 0.072(2) 0.0384(18) 0.073(2) 0.0041(16) 0.033(2) -0.0030(16) C9 0.0443(15) 0.0339(14) 0.0389(14) -0.0012(11) 0.0065(11) 0.0010(11) C10 0.0427(16) 0.0541(19) 0.0485(17) -0.0031(14) 0.0103(13) -0.0037(14) C11 0.0494(19) 0.063(2) 0.065(2) -0.0065(18) 0.0164(17) 0.0053(16) N3 0.075(2) 0.073(2) 0.076(2) 0.0207(19) 0.0148(19) 0.0022(19) N4 0.0543(18) 0.068(2) 0.084(2) -0.0013(18) 0.0145(17) -0.0043(16) C12 0.076(3) 0.063(3) 0.081(3) 0.018(2) 0.023(2) -0.006(2) C13 0.0446(19) 0.108(4) 0.062(2) 0.008(2) 0.0138(17) 0.002(2) C14 0.0534(19) 0.058(2) 0.0481(18) 0.0094(15) 0.0004(14) 0.0014(16) C15 0.0369(16) 0.106(4) 0.051(2) 0.014(2) 0.0024(14) 0.0000(19) C16 0.060(2) 0.078(3) 0.057(2) 0.016(2) 0.0068(18) 0.014(2) O14 0.177(5) 0.149(5) 0.103(3) 0.035(3) -0.020(3) -0.030(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O13 2.1496(19) 7_455 ? Mn1 O13 2.1496(19) . ? Mn1 O2 2.2168(18) 7_455 ? Mn1 O2 2.2168(18) . ? Mn1 O1 2.2383(17) 7_455 ? Mn1 O1 2.2383(17) . ? Cr1 O10 1.9765(19) . ? Cr1 O9 1.9813(17) . ? Cr1 O6 1.9837(17) . ? Cr1 O5 1.9861(18) . ? Cr1 O3 2.0039(17) . ? Cr1 O4 2.0154(17) . ? O1 C1 1.245(3) . ? O2 C2 1.252(3) . ? O3 C2 1.275(3) . ? O4 C1 1.286(3) . ? O5 C3 1.296(3) . ? O6 C4 1.300(3) . ? O7 C4 1.229(3) . ? O8 C3 1.232(3) . ? O9 C5 1.291(3) . ? O10 C6 1.298(3) . ? O11 C6 1.223(3) . ? O12 C5 1.231(3) . ? O13 H13A 0.7363 . ? O13 H13B 0.7549 . ? C1 C2 1.556(3) . ? C3 C4 1.564(4) . ? C5 C6 1.564(4) . ? N1 C7 1.346(6) . ? N1 C11 1.349(6) . ? N1 H1 0.8700 . ? N2 C9 1.321(4) . ? N2 H2A 0.8700 . ? N2 H2B 0.8700 . ? C7 C8 1.369(6) . ? C7 H7 0.9400 . ? C8 C9 1.425(5) . ? C8 H8 0.9400 . ? C9 C10 1.421(4) . ? C10 C11 1.356(5) . ? C10 H10 0.9400 . ? C11 H11 0.9400 . ? N3 C16 1.365(6) . ? N3 C12 1.357(6) . ? N3 H3 0.8700 . ? N4 C14 1.263(5) . ? N4 H4A 0.8700 . ? N4 H4B 0.8700 . ? C12 C13 1.330(7) . ? C12 H12 0.9400 . ? C13 C14 1.447(6) . ? C13 H13 0.9400 . ? C14 C15 1.419(6) . ? C15 C16 1.357(7) . ? C15 H15 0.9400 . ? C16 H16 0.9400 . ? O14 H14A 0.8939 . ? O14 H14B 0.8936 . ? O15 H15A 0.8943 . ? O16 H16A 0.9089 . ? O16 H16B 0.9103 . ? 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 O13 Mn1 O13 180.00(12) 7_455 . ? O13 Mn1 O2 94.68(7) 7_455 7_455 ? O13 Mn1 O2 85.32(7) . 7_455 ? O13 Mn1 O2 85.32(7) 7_455 . ? O13 Mn1 O2 94.68(7) . . ? O2 Mn1 O2 180.00(11) 7_455 . ? O13 Mn1 O1 86.05(7) 7_455 7_455 ? O13 Mn1 O1 93.95(7) . 7_455 ? O2 Mn1 O1 76.70(6) 7_455 7_455 ? O2 Mn1 O1 103.30(6) . 7_455 ? O13 Mn1 O1 93.95(7) 7_455 . ? O13 Mn1 O1 86.05(7) . . ? O2 Mn1 O1 103.30(6) 7_455 . ? O2 Mn1 O1 76.70(6) . . ? O1 Mn1 O1 180.00(12) 7_455 . ? O13 Mn1 Cr1 89.48(5) 7_455 . ? O13 Mn1 Cr1 90.52(5) . . ? O2 Mn1 Cr1 141.88(4) 7_455 . ? O2 Mn1 Cr1 38.12(4) . . ? O1 Mn1 Cr1 141.42(4) 7_455 . ? O1 Mn1 Cr1 38.58(4) . . ? O10 Cr1 O9 83.14(7) . . ? O10 Cr1 O6 91.48(8) . . ? O9 Cr1 O6 171.33(7) . . ? O10 Cr1 O5 92.64(8) . . ? O9 Cr1 O5 90.96(8) . . ? O6 Cr1 O5 82.48(7) . . ? O10 Cr1 O3 92.72(8) . . ? O9 Cr1 O3 94.75(8) . . ? O6 Cr1 O3 92.28(7) . . ? O5 Cr1 O3 172.60(8) . . ? O10 Cr1 O4 173.59(7) . . ? O9 Cr1 O4 93.11(7) . . ? O6 Cr1 O4 92.84(7) . . ? O5 Cr1 O4 92.62(7) . . ? O3 Cr1 O4 82.38(7) . . ? O10 Cr1 Mn1 133.51(6) . . ? O9 Cr1 Mn1 96.38(5) . . ? O6 Cr1 Mn1 92.26(5) . . ? O5 Cr1 Mn1 133.78(6) . . ? O3 Cr1 Mn1 40.83(5) . . ? O4 Cr1 Mn1 41.57(5) . . ? C1 O1 Mn1 112.34(15) . . ? C2 O2 Mn1 113.05(15) . . ? C2 O3 Cr1 113.85(15) . . ? C1 O4 Cr1 113.31(14) . . ? C3 O5 Cr1 114.62(16) . . ? C4 O6 Cr1 114.74(15) . . ? C5 O9 Cr1 114.19(15) . . ? C6 O10 Cr1 114.04(16) . . ? Mn1 O13 H13A 119.0 . . ? Mn1 O13 H13B 113.9 . . ? H13A O13 H13B 105.4 . . ? O1 C1 O4 125.9(2) . . ? O1 C1 C2 119.2(2) . . ? O4 C1 C2 114.98(19) . . ? O2 C2 O3 125.8(2) . . ? O2 C2 C1 118.7(2) . . ? O3 C2 C1 115.44(19) . . ? O8 C3 O5 125.1(3) . . ? O8 C3 C4 120.7(2) . . ? O5 C3 C4 114.2(2) . . ? O7 C4 O6 124.9(2) . . ? O7 C4 C3 121.3(2) . . ? O6 C4 C3 113.7(2) . . ? O12 C5 O9 126.4(2) . . ? O12 C5 C6 119.3(2) . . ? O9 C5 C6 114.2(2) . . ? O11 C6 O10 125.9(3) . . ? O11 C6 C5 119.8(2) . . ? O10 C6 C5 114.2(2) . . ? C7 N1 C11 120.3(3) . . ? C7 N1 H1 119.8 . . ? C11 N1 H1 119.8 . . ? C9 N2 H2A 120.0 . . ? C9 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? N1 C7 C8 121.6(4) . . ? N1 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C7 C8 C9 119.7(3) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? N2 C9 C10 121.8(3) . . ? N2 C9 C8 121.9(3) . . ? C10 C9 C8 116.2(3) . . ? C11 C10 C9 120.7(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? N1 C11 C10 121.3(3) . . ? N1 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C16 N3 C12 120.8(4) . . ? C16 N3 H3 119.6 . . ? C12 N3 H3 119.6 . . ? C14 N4 H4A 120.0 . . ? C14 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C13 C12 N3 120.8(4) . . ? C13 C12 H12 119.6 . . ? N3 C12 H12 119.6 . . ? C12 C13 C14 121.1(4) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? N4 C14 C15 121.1(4) . . ? N4 C14 C13 122.9(4) . . ? C15 C14 C13 116.0(4) . . ? C16 C15 C14 120.1(4) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 N3 121.1(4) . . ? C15 C16 H16 119.4 . . ? N3 C16 H16 119.4 . . ? H14A O14 H14B 116.7 . . ? H16A O16 H16B 104.8 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.798 _refine_diff_density_min -0.760 _refine_diff_density_rms 0.091 # Attachment 'emil19F2.cif' data_emil19 _database_code_depnum_ccdc_archive 'CCDC 762573' #TrackingRef 'emil19F2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C12 H4 Co Cr2 O26), 4(C5 H7 N2), 3.25(O)' _chemical_formula_sum 'C32 H32 Co Cr2 N8 O29.25' _chemical_formula_weight 1159.58 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cr Cr 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.4334(16) _cell_length_b 20.243(2) _cell_length_c 21.805(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.113(9) _cell_angle_gamma 90.00 _cell_volume 4951.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 230 _cell_measurement_theta_min 4.16 _cell_measurement_theta_max 22.22 _exptl_crystal_description 'hexagonal plate' _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2356 _exptl_absorpt_coefficient_mu 0.861 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7561 _exptl_absorpt_correction_T_max 0.8914 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _diffrn_ambient_temperature 250(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12147 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0681 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 30.02 _reflns_number_total 7010 _reflns_number_gt 4327 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV, 1997-2000)' _computing_cell_refinement 'DIRAX/LSQ (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _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^)+(0.0305P)^2^+1.0401P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7010 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0866 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1395 _refine_ls_wR_factor_gt 0.1101 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 Co1 Co -0.2500 0.2500 0.5000 0.0225(2) Uani 1 2 d S . . Cr1 Cr 0.18367(5) 0.21314(3) 0.64890(3) 0.02145(18) Uani 1 1 d . . . O1 O -0.1113(2) 0.17625(13) 0.52059(12) 0.0264(6) Uani 1 1 d . . . O2 O -0.1246(2) 0.29994(13) 0.57013(13) 0.0273(6) Uani 1 1 d . . . O3 O 0.0555(2) 0.28240(13) 0.63116(13) 0.0268(6) Uani 1 1 d . . . O4 O 0.0665(2) 0.16206(12) 0.58486(12) 0.0238(5) Uani 1 1 d . . . O5 O 0.3092(2) 0.14382(13) 0.65410(13) 0.0305(6) Uani 1 1 d . . . O6 O 0.2680(2) 0.24993(13) 0.58501(13) 0.0274(6) Uani 1 1 d . . . O7 O 0.4334(3) 0.23560(17) 0.54490(15) 0.0414(8) Uani 1 1 d . . . O8 O 0.4751(3) 0.11967(17) 0.61764(19) 0.0543(10) Uani 1 1 d . . . O9 O 0.1241(2) 0.17359(14) 0.72019(12) 0.0287(6) Uani 1 1 d . . . O10 O 0.2821(3) 0.26674(14) 0.71488(13) 0.0322(6) Uani 1 1 d . . . O11 O 0.3267(4) 0.2743(2) 0.81957(17) 0.0699(13) Uani 1 1 d . . . O12 O 0.1602(3) 0.17556(16) 0.82536(14) 0.0438(8) Uani 1 1 d . . . O13 O -0.3309(3) 0.20343(15) 0.56398(13) 0.0361(7) Uani 1 1 d . . . H13A H -0.3005 0.1997 0.5957 0.043 Uiso 1 1 d R . . H13B H -0.4005 0.2084 0.5624 0.043 Uiso 1 1 d R . . C1 C -0.0279(3) 0.19493(17) 0.56213(16) 0.0211(7) Uani 1 1 d . . . C2 C -0.0346(3) 0.26538(17) 0.59012(17) 0.0223(7) Uani 1 1 d . . . C3 C 0.3880(3) 0.1547(2) 0.6200(2) 0.0309(8) Uani 1 1 d . . . C4 C 0.3650(3) 0.2185(2) 0.57900(18) 0.0280(8) Uani 1 1 d . . . C5 C 0.1766(4) 0.1952(2) 0.77412(19) 0.0299(8) Uani 1 1 d . . . C6 C 0.2710(4) 0.2505(2) 0.7713(2) 0.0362(10) Uani 1 1 d . . . N1 N 0.1298(6) 0.5465(3) 0.5529(3) 0.089(2) Uani 1 1 d . . . H1 H 0.0979 0.5831 0.5624 0.106 Uiso 1 1 calc R . . N2 N 0.2902(4) 0.3749(2) 0.5165(2) 0.0540(11) Uani 1 1 d . . . H2A H 0.2691 0.3378 0.5314 0.065 Uiso 1 1 calc R . . H2B H 0.3471 0.3754 0.4952 0.065 Uiso 1 1 calc R . . C7 C 0.2115(7) 0.5482(4) 0.5201(4) 0.085(2) Uani 1 1 d . . . H7 H 0.2307 0.5892 0.5044 0.102 Uiso 1 1 calc R . . C8 C 0.2732(7) 0.4925(3) 0.5067(3) 0.0688(18) Uani 1 1 d . . . H8 H 0.3372 0.4960 0.4855 0.083 Uiso 1 1 calc R . . C9 C 0.2360(5) 0.4299(3) 0.5261(3) 0.0517(13) Uani 1 1 d . . . C10 C 0.1428(5) 0.4318(3) 0.5604(3) 0.0557(14) Uani 1 1 d . . . H10 H 0.1161 0.3918 0.5748 0.067 Uiso 1 1 calc R . . C11 C 0.0920(6) 0.4872(3) 0.5731(3) 0.0684(17) Uani 1 1 d . . . H11 H 0.0301 0.4863 0.5958 0.082 Uiso 1 1 calc R . . N3 N 0.4655(6) 0.5486(3) 0.6707(3) 0.089(2) Uani 1 1 d . . . H3 H 0.4670 0.5916 0.6720 0.107 Uiso 1 1 calc R . . N4 N 0.4657(5) 0.3520(3) 0.6739(3) 0.0831(18) Uani 1 1 d . . . H4A H 0.4075 0.3309 0.6857 0.100 Uiso 1 1 calc R . . H4B H 0.5254 0.3301 0.6646 0.100 Uiso 1 1 calc R . . C12 C 0.5596(7) 0.5157(4) 0.6535(4) 0.081(2) Uani 1 1 d . . . H12 H 0.6230 0.5392 0.6420 0.097 Uiso 1 1 calc R . . C13 C 0.5590(6) 0.4514(4) 0.6536(3) 0.078(2) Uani 1 1 d . . . H13 H 0.6234 0.4289 0.6421 0.093 Uiso 1 1 calc R . . C14 C 0.4637(6) 0.4132(3) 0.6704(3) 0.0666(17) Uani 1 1 d . . . C15 C 0.3660(5) 0.4489(4) 0.6857(3) 0.076(2) Uani 1 1 d . . . H15 H 0.3002 0.4264 0.6957 0.091 Uiso 1 1 calc R . . C16 C 0.3693(6) 0.5161(4) 0.6857(3) 0.0755(19) Uani 1 1 d . . . H16 H 0.3057 0.5404 0.6960 0.091 Uiso 1 1 calc R . . O14 O 0.3746(9) 0.0672(4) 0.7695(4) 0.151(3) Uani 1 1 d . . . O15 O 0.5000 -0.110(4) 0.7500 0.22(3) Uiso 0.25 2 d SP . . O16 O 0.364(2) -0.0833(11) 0.6472(11) 0.194(8) Uiso 0.50 1 d P . . 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 Co1 0.0179(4) 0.0300(4) 0.0204(3) 0.0005(3) 0.0055(3) 0.0014(3) Cr1 0.0181(3) 0.0252(3) 0.0220(3) 0.0019(2) 0.0062(2) 0.0005(2) O1 0.0221(13) 0.0280(13) 0.0295(13) -0.0042(11) 0.0060(10) 0.0013(10) O2 0.0229(13) 0.0284(13) 0.0305(14) -0.0032(11) 0.0048(11) 0.0063(10) O3 0.0229(13) 0.0273(13) 0.0297(14) -0.0055(11) 0.0036(11) 0.0014(10) O4 0.0213(13) 0.0240(13) 0.0264(13) -0.0014(10) 0.0050(10) 0.0023(10) O5 0.0259(14) 0.0331(14) 0.0353(15) 0.0116(12) 0.0129(12) 0.0068(11) O6 0.0245(14) 0.0306(14) 0.0293(14) 0.0086(11) 0.0108(11) 0.0038(10) O7 0.0307(16) 0.059(2) 0.0397(17) 0.0156(15) 0.0199(14) 0.0032(14) O8 0.048(2) 0.051(2) 0.071(3) 0.0205(18) 0.0304(19) 0.0273(17) O9 0.0267(14) 0.0354(15) 0.0265(13) -0.0015(11) 0.0112(10) -0.0082(11) O10 0.0311(15) 0.0368(15) 0.0284(14) 0.0035(12) 0.0048(12) -0.0100(12) O11 0.093(3) 0.078(3) 0.0330(19) 0.0006(18) -0.001(2) -0.053(2) O12 0.055(2) 0.0509(19) 0.0286(15) 0.0011(14) 0.0159(14) -0.0171(16) O13 0.0250(14) 0.063(2) 0.0224(13) 0.0094(13) 0.0104(11) 0.0011(13) C1 0.0231(17) 0.0212(16) 0.0212(16) -0.0006(13) 0.0095(13) -0.0009(13) C2 0.0227(18) 0.0235(17) 0.0226(16) -0.0018(13) 0.0090(13) 0.0028(13) C3 0.0246(19) 0.036(2) 0.034(2) 0.0045(16) 0.0099(16) 0.0054(16) C4 0.0239(19) 0.034(2) 0.0271(18) 0.0040(15) 0.0075(15) -0.0014(15) C5 0.033(2) 0.0300(19) 0.0295(19) -0.0017(15) 0.0115(16) -0.0026(16) C6 0.041(2) 0.039(2) 0.028(2) 0.0007(17) 0.0053(18) -0.0109(18) N1 0.072(4) 0.084(4) 0.106(5) -0.028(4) 0.009(4) 0.033(3) N2 0.075(3) 0.038(2) 0.055(3) 0.0029(19) 0.026(2) 0.014(2) C7 0.084(5) 0.062(4) 0.109(6) -0.006(4) 0.020(5) -0.003(4) C8 0.094(5) 0.037(3) 0.087(5) 0.009(3) 0.045(4) 0.006(3) C9 0.057(3) 0.046(3) 0.051(3) 0.001(2) 0.009(2) 0.002(2) C10 0.042(3) 0.074(4) 0.053(3) -0.013(3) 0.015(2) -0.004(3) C11 0.065(4) 0.065(4) 0.077(4) -0.009(3) 0.018(3) 0.004(3) N3 0.080(4) 0.090(4) 0.100(5) 0.041(4) 0.022(4) 0.003(4) N4 0.072(4) 0.081(4) 0.101(5) -0.004(4) 0.028(4) -0.007(3) C12 0.082(5) 0.077(5) 0.089(5) 0.037(4) 0.030(4) -0.003(4) C13 0.047(3) 0.120(6) 0.067(4) 0.018(4) 0.017(3) 0.008(4) C14 0.078(4) 0.066(4) 0.049(3) 0.019(3) -0.004(3) -0.006(3) C15 0.038(3) 0.131(7) 0.055(4) 0.031(4) 0.000(3) 0.002(4) C16 0.066(4) 0.095(5) 0.062(4) 0.031(4) 0.003(3) 0.011(4) O14 0.202(8) 0.132(6) 0.110(6) 0.022(5) 0.007(6) -0.007(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O13 2.046(3) . ? Co1 O13 2.046(3) 7_456 ? Co1 O2 2.138(3) 7_456 ? Co1 O2 2.138(3) . ? Co1 O1 2.161(3) 7_456 ? Co1 O1 2.161(3) . ? Cr1 O10 1.972(3) . ? Cr1 O9 1.982(3) . ? Cr1 O6 1.986(3) . ? Cr1 O5 1.995(3) . ? Cr1 O3 2.011(3) . ? Cr1 O4 2.023(3) . ? O1 C1 1.241(4) . ? O2 C2 1.251(4) . ? O3 C2 1.275(4) . ? O4 C1 1.284(4) . ? O5 C3 1.292(5) . ? O6 C4 1.307(5) . ? O7 C4 1.228(5) . ? O8 C3 1.232(5) . ? O9 C5 1.289(5) . ? O10 C6 1.302(5) . ? O11 C6 1.220(5) . ? O12 C5 1.234(5) . ? O13 H13A 0.7164 . ? O13 H13B 0.7959 . ? C1 C2 1.559(5) . ? C3 C4 1.564(6) . ? C5 C6 1.564(6) . ? N1 C7 1.281(10) . ? N1 C11 1.375(9) . ? N1 H1 0.8700 . ? N2 C9 1.310(7) . ? N2 H2A 0.8700 . ? N2 H2B 0.8700 . ? C7 C8 1.391(10) . ? C7 H7 0.9400 . ? C8 C9 1.428(8) . ? C8 H8 0.9400 . ? C9 C10 1.416(8) . ? C10 C11 1.317(8) . ? C10 H10 0.9400 . ? C11 H11 0.9400 . ? N3 C16 1.374(9) . ? N3 C12 1.377(10) . ? N3 H3 0.8700 . ? N4 C14 1.243(8) . ? N4 H4A 0.8700 . ? N4 H4B 0.8700 . ? C12 C13 1.303(11) . ? C12 H12 0.9400 . ? C13 C14 1.439(10) . ? C13 H13 0.9400 . ? C14 C15 1.423(10) . ? C15 C16 1.361(11) . ? C15 H15 0.9400 . ? C16 H16 0.9400 . ? 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 O13 Co1 O13 180.000(1) . 7_456 ? O13 Co1 O2 86.61(11) . 7_456 ? O13 Co1 O2 93.39(11) 7_456 7_456 ? O13 Co1 O2 93.39(11) . . ? O13 Co1 O2 86.61(11) 7_456 . ? O2 Co1 O2 180.000(1) 7_456 . ? O13 Co1 O1 92.86(11) . 7_456 ? O13 Co1 O1 87.14(11) 7_456 7_456 ? O2 Co1 O1 79.28(10) 7_456 7_456 ? O2 Co1 O1 100.72(10) . 7_456 ? O13 Co1 O1 87.14(11) . . ? O13 Co1 O1 92.86(11) 7_456 . ? O2 Co1 O1 100.72(10) 7_456 . ? O2 Co1 O1 79.28(10) . . ? O1 Co1 O1 180.00(14) 7_456 . ? O10 Cr1 O9 83.34(11) . . ? O10 Cr1 O6 91.12(12) . . ? O9 Cr1 O6 171.26(11) . . ? O10 Cr1 O5 92.44(12) . . ? O9 Cr1 O5 91.36(12) . . ? O6 Cr1 O5 82.09(11) . . ? O10 Cr1 O3 92.80(12) . . ? O9 Cr1 O3 94.84(12) . . ? O6 Cr1 O3 92.18(11) . . ? O5 Cr1 O3 172.31(12) . . ? O10 Cr1 O4 173.50(12) . . ? O9 Cr1 O4 93.04(11) . . ? O6 Cr1 O4 93.08(11) . . ? O5 Cr1 O4 93.04(11) . . ? O3 Cr1 O4 82.10(10) . . ? C1 O1 Co1 111.8(2) . . ? C2 O2 Co1 112.2(2) . . ? C2 O3 Cr1 114.0(2) . . ? C1 O4 Cr1 113.4(2) . . ? C3 O5 Cr1 114.9(2) . . ? C4 O6 Cr1 115.1(2) . . ? C5 O9 Cr1 114.1(2) . . ? C6 O10 Cr1 113.8(3) . . ? Co1 O13 H13A 120.6 . . ? Co1 O13 H13B 119.5 . . ? H13A O13 H13B 110.5 . . ? O1 C1 O4 126.5(3) . . ? O1 C1 C2 118.4(3) . . ? O4 C1 C2 115.1(3) . . ? O2 C2 O3 126.3(3) . . ? O2 C2 C1 118.3(3) . . ? O3 C2 C1 115.3(3) . . ? O8 C3 O5 125.8(4) . . ? O8 C3 C4 120.0(4) . . ? O5 C3 C4 114.3(3) . . ? O7 C4 O6 125.1(4) . . ? O7 C4 C3 121.5(4) . . ? O6 C4 C3 113.4(3) . . ? O12 C5 O9 126.3(4) . . ? O12 C5 C6 119.5(4) . . ? O9 C5 C6 114.2(3) . . ? O11 C6 O10 125.9(4) . . ? O11 C6 C5 119.8(4) . . ? O10 C6 C5 114.3(3) . . ? C7 N1 C11 120.7(6) . . ? C7 N1 H1 119.7 . . ? C11 N1 H1 119.7 . . ? C9 N2 H2A 120.0 . . ? C9 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? N1 C7 C8 123.3(7) . . ? N1 C7 H7 118.3 . . ? C8 C7 H7 118.4 . . ? C7 C8 C9 117.7(6) . . ? C7 C8 H8 121.1 . . ? C9 C8 H8 121.1 . . ? N2 C9 C10 122.3(5) . . ? N2 C9 C8 122.0(6) . . ? C10 C9 C8 115.5(5) . . ? C11 C10 C9 122.7(6) . . ? C11 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? C10 C11 N1 119.9(6) . . ? C10 C11 H11 120.1 . . ? N1 C11 H11 120.1 . . ? C16 N3 C12 122.5(7) . . ? C16 N3 H3 118.8 . . ? C12 N3 H3 118.8 . . ? C14 N4 H4A 120.0 . . ? C14 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C13 C12 N3 118.6(7) . . ? C13 C12 H12 120.7 . . ? N3 C12 H12 120.7 . . ? C12 C13 C14 122.8(7) . . ? C12 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? N4 C14 C15 119.9(7) . . ? N4 C14 C13 123.0(7) . . ? C15 C14 C13 117.0(6) . . ? C16 C15 C14 119.0(7) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 N3 120.1(7) . . ? C15 C16 H16 119.9 . . ? N3 C16 H16 119.9 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.911 _refine_diff_density_min -0.962 _refine_diff_density_rms 0.139