# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Bernhard Spingler' _publ_contact_author_email spingler@aci.uzh.ch loop_ _publ_author_name 'Alfredo Medina-Molner' 'Bernhard Spingler' data_am181203 _database_code_depnum_ccdc_archive 'CCDC 661093' #TrackingRef 'web_deposit_cif_file_0_BernhardSpingler_1312475891.1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H60 F6 N6 Ni2 O14 S2' _chemical_formula_weight 988.35 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 16.1025(10) _cell_length_b 15.5813(8) _cell_length_c 17.0644(11) _cell_angle_alpha 90.00 _cell_angle_beta 98.454(8) _cell_angle_gamma 90.00 _cell_volume 4234.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2072 _exptl_absorpt_coefficient_mu 1.080 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7695 _exptl_absorpt_correction_T_max 0.9064 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '/f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 11 _diffrn_standards_decay_% ? _diffrn_reflns_number 17183 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 30.47 _reflns_number_total 6269 _reflns_number_gt 4594 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _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^)+(0.1306P)^2^+2.3058P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0085(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6269 _refine_ls_number_parameters 305 _refine_ls_number_restraints 95 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.2106 _refine_ls_wR_factor_gt 0.1939 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.073 _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 Ni1 Ni 0.09357(2) 0.19926(2) 0.05704(2) 0.03972(17) Uani 1 1 d . A . C1A C 0.0759(4) 0.3680(4) 0.1256(4) 0.0512(12) Uani 0.55 1 d PU A 1 C1B C 0.1707(4) 0.3532(5) 0.1469(5) 0.0480(13) Uani 0.45 1 d PU A 2 C2 C 0.1267(2) 0.3392(3) 0.2126(3) 0.0629(10) Uani 1 1 d . . . C3 C 0.1343(3) 0.2435(4) 0.2277(3) 0.0793(14) Uani 1 1 d . A . H3A H 0.1911 0.2259 0.2225 0.095 Uiso 1 1 calc R . . H3B H 0.1262 0.2326 0.2821 0.095 Uiso 1 1 calc R . . C4 C -0.0090(4) 0.1887(3) 0.1975(3) 0.0753(13) Uani 1 1 d . A . H4A H -0.0238 0.2473 0.2085 0.090 Uiso 1 1 calc R . . H4B H -0.0070 0.1564 0.2463 0.090 Uiso 1 1 calc R . . C5 C -0.0774(3) 0.1517(3) 0.1371(4) 0.0777(15) Uani 1 1 d . . . H5A H -0.0605 0.0948 0.1225 0.093 Uiso 1 1 calc R . . H5B H -0.1279 0.1453 0.1615 0.093 Uiso 1 1 calc R . . C6 C -0.0981(3) 0.2046(4) 0.0632(5) 0.095(2) Uani 1 1 d . A . H6A H -0.1501 0.1834 0.0337 0.114 Uiso 1 1 calc R . . H6B H -0.1077 0.2633 0.0784 0.114 Uiso 1 1 calc R . . C7 C -0.0502(5) 0.2711(5) -0.0541(4) 0.114(3) Uani 1 1 d . A . H7A H -0.1092 0.2690 -0.0762 0.137 Uiso 1 1 calc R . . H7B H -0.0180 0.2573 -0.0962 0.137 Uiso 1 1 calc R . . C8 C -0.0282(3) 0.3622(3) -0.0246(3) 0.0724(13) Uani 1 1 d . . . C9A C 0.0595(4) 0.3688(4) -0.0188(4) 0.0520(12) Uani 0.55 1 d PU A 1 C9B C 0.0389(4) 0.3833(5) 0.0586(5) 0.0449(12) Uani 0.45 1 d PU A 2 C10A C 0.1998(4) 0.3597(4) 0.0584(4) 0.0494(11) Uani 0.55 1 d PU A 1 C10B C 0.1689(4) 0.3678(4) 0.0041(5) 0.0420(12) Uani 0.45 1 d PU A 2 C11 C 0.2500 0.3301(3) 0.0000 0.0667(16) Uani 1 2 d S . . C20 C 0.1883(2) 0.0706(2) 0.0847(2) 0.0491(7) Uani 1 1 d . A . C21 C 0.2483(3) -0.0029(3) 0.1031(3) 0.0596(9) Uani 1 1 d . . . H21A H 0.2678 -0.0045 0.1590 0.072 Uiso 1 1 calc R . . H21B H 0.2953 0.0045 0.0750 0.072 Uiso 1 1 calc R . . H21C H 0.2203 -0.0558 0.0871 0.072 Uiso 1 1 calc R . . C22 C 0.2338(3) -0.1169(3) 0.3097(4) 0.0740(13) Uani 1 1 d . . . N1 N 0.11495(18) 0.33233(19) 0.06049(18) 0.0474(6) Uani 1 1 d . . . N2 N 0.0745(3) 0.1887(2) 0.1746(2) 0.0597(8) Uani 1 1 d D . . H27 H 0.078(3) 0.1339(15) 0.188(3) 0.072 Uiso 1 1 d D . . N3 N -0.03302(19) 0.2050(2) 0.0097(2) 0.0575(8) Uani 1 1 d . . . H26 H -0.034(3) 0.161(4) -0.009(3) 0.069 Uiso 1 1 d . . . O20 O 0.21712(14) 0.14731(15) 0.09100(16) 0.0492(5) Uani 1 1 d . . . O21 O 0.11076(15) 0.05854(16) 0.06382(15) 0.0508(5) Uani 1 1 d . . . O22 O 0.16289(18) 0.02609(18) 0.2624(2) 0.0641(7) Uani 1 1 d . . . O23 O 0.0765(2) -0.0974(3) 0.2771(2) 0.0832(10) Uani 1 1 d . . . O24 O 0.1470(3) -0.0278(3) 0.3925(2) 0.1014(13) Uani 1 1 d . . . O25 O 0.11616(15) 0.18063(16) -0.06297(15) 0.0457(5) Uani 1 1 d D . . H22 H 0.084(2) 0.142(2) -0.079(3) 0.055 Uiso 1 1 d D . . H23 H 0.1644(15) 0.170(3) -0.068(3) 0.055 Uiso 1 1 d D . . O26 O -0.01182(19) 0.0706(2) -0.11779(18) 0.0652(7) Uani 1 1 d D . . H24 H -0.042(3) 0.037(3) -0.099(3) 0.078 Uiso 1 1 d D . . H25 H -0.026(3) 0.075(4) -0.1666(13) 0.078 Uiso 1 1 d D . . F22 F 0.30580(18) -0.0779(3) 0.3256(4) 0.147(2) Uani 1 1 d . . . F23 F 0.2324(2) -0.1835(2) 0.3581(2) 0.0888(10) Uani 1 1 d . . . F24 F 0.2326(3) -0.1499(2) 0.2361(3) 0.1227(17) Uani 1 1 d . . . S22 S 0.14534(5) -0.04526(6) 0.31112(5) 0.0499(2) 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 Ni1 0.0354(2) 0.0409(2) 0.0428(3) 0.00347(14) 0.00577(15) 0.00100(13) C1A 0.050(2) 0.046(2) 0.059(3) -0.004(2) 0.013(2) 0.007(2) C1B 0.043(3) 0.050(3) 0.050(3) -0.007(2) 0.005(2) -0.003(2) C2 0.0529(18) 0.079(3) 0.057(2) -0.0234(19) 0.0118(16) 0.0007(18) C3 0.081(3) 0.086(3) 0.062(3) -0.019(2) -0.019(2) 0.023(2) C4 0.089(3) 0.070(3) 0.076(3) -0.001(2) 0.044(3) -0.011(2) C5 0.067(2) 0.052(2) 0.125(4) -0.018(2) 0.050(3) -0.0156(18) C6 0.0422(19) 0.093(4) 0.150(6) -0.054(4) 0.020(3) -0.013(2) C7 0.127(5) 0.143(6) 0.064(3) -0.012(3) -0.016(3) 0.084(5) C8 0.068(2) 0.083(3) 0.069(3) 0.025(2) 0.018(2) 0.039(2) C9A 0.049(2) 0.052(3) 0.055(3) 0.005(2) 0.008(2) 0.004(2) C9B 0.036(2) 0.049(3) 0.051(3) -0.003(2) 0.008(2) 0.011(2) C10A 0.045(2) 0.046(2) 0.059(3) -0.003(2) 0.012(2) -0.002(2) C10B 0.040(2) 0.037(2) 0.050(3) 0.004(2) 0.010(2) 0.004(2) C11 0.064(3) 0.043(2) 0.104(5) 0.000 0.046(3) 0.000 C20 0.0458(15) 0.0515(17) 0.0514(18) 0.0087(14) 0.0113(13) 0.0044(13) C21 0.063(2) 0.0485(18) 0.068(2) 0.0111(16) 0.0134(17) 0.0153(15) C22 0.063(2) 0.055(2) 0.109(4) 0.024(2) 0.029(2) 0.0034(18) N1 0.0449(12) 0.0408(13) 0.0593(17) 0.0027(11) 0.0173(11) 0.0046(10) N2 0.076(2) 0.0563(18) 0.0493(17) 0.0029(13) 0.0176(15) 0.0046(15) N3 0.0411(14) 0.0640(19) 0.064(2) -0.0180(15) -0.0040(13) 0.0110(12) O20 0.0397(10) 0.0461(12) 0.0623(15) 0.0088(10) 0.0096(10) 0.0032(9) O21 0.0489(11) 0.0472(12) 0.0567(14) 0.0080(10) 0.0093(10) -0.0010(9) O22 0.0642(15) 0.0465(13) 0.084(2) 0.0063(13) 0.0186(14) 0.0015(11) O23 0.0657(18) 0.099(3) 0.080(2) 0.0202(19) -0.0046(15) -0.0276(17) O24 0.151(4) 0.097(3) 0.059(2) -0.0146(19) 0.024(2) 0.027(3) O25 0.0459(11) 0.0467(11) 0.0458(12) 0.0020(9) 0.0107(9) -0.0014(9) O26 0.0666(17) 0.0702(18) 0.0558(16) 0.0028(14) -0.0014(13) -0.0215(14) F22 0.0472(14) 0.110(3) 0.279(6) 0.083(4) 0.011(2) 0.0001(16) F23 0.0818(18) 0.0766(18) 0.113(3) 0.0415(17) 0.0309(17) 0.0172(14) F24 0.191(4) 0.074(2) 0.127(3) 0.015(2) 0.102(3) 0.039(2) S22 0.0486(4) 0.0516(4) 0.0500(5) -0.0021(3) 0.0092(3) 0.0000(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 Ni1 N2 2.080(3) . ? Ni1 N3 2.081(3) . ? Ni1 N1 2.101(3) . ? Ni1 O20 2.147(2) . ? Ni1 O25 2.152(2) . ? Ni1 O21 2.211(3) . ? C1A N1 1.464(7) . ? C1A C2 1.648(9) . ? C1B C2 1.429(9) . ? C1B N1 1.642(8) . ? C2 C3 1.515(8) . ? C3 N2 1.491(6) . ? C4 N2 1.454(6) . ? C4 C5 1.508(8) . ? C5 C6 1.503(10) . ? C6 N3 1.487(7) . ? C7 N3 1.494(8) . ? C7 C8 1.530(10) . ? C8 C9A 1.405(8) . ? C8 C9B 1.686(9) . ? C9A N1 1.611(7) . ? C9B N1 1.456(7) . ? C10A N1 1.437(6) . ? C10A C11 1.448(6) . ? C10B C11 1.442(7) . ? C10B N1 1.494(7) . ? C11 C10B 1.442(7) 2 ? C11 C10A 1.448(6) 2 ? C20 O21 1.261(4) . ? C20 O20 1.281(4) . ? C20 C21 1.503(5) . ? C22 F22 1.302(6) . ? C22 F23 1.328(5) . ? C22 F24 1.355(7) . ? C22 S22 1.813(5) . ? O22 S22 1.441(3) . ? O23 S22 1.427(3) . ? O24 S22 1.411(4) . ? 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 N2 Ni1 N3 95.92(16) . . ? N2 Ni1 N1 95.64(13) . . ? N3 Ni1 N1 96.63(13) . . ? N2 Ni1 O20 88.38(13) . . ? N3 Ni1 O20 159.51(12) . . ? N1 Ni1 O20 102.88(10) . . ? N2 Ni1 O25 167.62(12) . . ? N3 Ni1 O25 85.94(12) . . ? N1 Ni1 O25 96.31(10) . . ? O20 Ni1 O25 85.78(10) . . ? N2 Ni1 O21 84.59(12) . . ? N3 Ni1 O21 99.84(12) . . ? N1 Ni1 O21 163.42(11) . . ? O20 Ni1 O21 60.53(9) . . ? O25 Ni1 O21 83.03(9) . . ? N1 C1A C2 111.6(4) . . ? C2 C1B N1 113.9(5) . . ? C1B C2 C3 104.3(4) . . ? C1B C2 C1A 59.3(4) . . ? C3 C2 C1A 116.0(4) . . ? N2 C3 C2 115.5(4) . . ? N2 C4 C5 115.4(4) . . ? C6 C5 C4 114.4(4) . . ? N3 C6 C5 115.4(4) . . ? N3 C7 C8 113.0(4) . . ? C9A C8 C7 105.8(5) . . ? C9A C8 C9B 54.1(4) . . ? C7 C8 C9B 123.2(4) . . ? C8 C9A N1 117.4(5) . . ? N1 C9B C8 110.2(5) . . ? N1 C10A C11 123.4(5) . . ? C11 C10B N1 119.8(5) . . ? C10B C11 C10B 131.9(7) 2 . ? C10B C11 C10A 40.2(4) 2 2 ? C10B C11 C10A 120.3(4) . 2 ? C10B C11 C10A 120.3(4) 2 . ? C10B C11 C10A 40.2(4) . . ? C10A C11 C10A 142.8(6) 2 . ? O21 C20 O20 119.7(3) . . ? O21 C20 C21 121.7(3) . . ? O20 C20 C21 118.6(3) . . ? F22 C22 F23 109.4(5) . . ? F22 C22 F24 105.1(5) . . ? F23 C22 F24 106.3(4) . . ? F22 C22 S22 112.8(4) . . ? F23 C22 S22 112.8(3) . . ? F24 C22 S22 110.0(4) . . ? C10A N1 C9B 129.6(4) . . ? C10A N1 C1A 114.9(4) . . ? C9B N1 C1A 49.9(4) . . ? C10A N1 C10B 39.6(4) . . ? C9B N1 C10B 110.6(4) . . ? C1A N1 C10B 134.7(4) . . ? C10A N1 C9A 106.6(4) . . ? C9B N1 C9A 55.2(4) . . ? C1A N1 C9A 104.9(4) . . ? C10B N1 C9A 68.4(4) . . ? C10A N1 C1B 64.3(4) . . ? C9B N1 C1B 105.0(4) . . ? C1A N1 C1B 58.8(4) . . ? C10B N1 C1B 102.2(4) . . ? C9A N1 C1B 147.8(4) . . ? C10A N1 Ni1 116.4(3) . . ? C9B N1 Ni1 113.8(3) . . ? C1A N1 Ni1 108.0(3) . . ? C10B N1 Ni1 117.1(3) . . ? C9A N1 Ni1 104.8(3) . . ? C1B N1 Ni1 106.6(3) . . ? C4 N2 C3 112.1(4) . . ? C4 N2 Ni1 122.2(3) . . ? C3 N2 Ni1 111.6(3) . . ? C6 N3 C7 112.2(4) . . ? C6 N3 Ni1 120.0(3) . . ? C7 N3 Ni1 112.2(4) . . ? C20 O20 Ni1 91.07(19) . . ? C20 O21 Ni1 88.7(2) . . ? O24 S22 O23 114.3(3) . . ? O24 S22 O22 116.2(2) . . ? O23 S22 O22 114.3(2) . . ? O24 S22 C22 103.3(3) . . ? O23 S22 C22 102.0(3) . . ? O22 S22 C22 104.27(18) . . ? 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 N1 C1B C2 C3 82.1(6) . . . . ? N1 C1B C2 C1A -30.0(4) . . . . ? N1 C1A C2 C1B 33.4(5) . . . . ? N1 C1A C2 C3 -58.3(6) . . . . ? C1B C2 C3 N2 -80.4(6) . . . . ? C1A C2 C3 N2 -18.0(6) . . . . ? N2 C4 C5 C6 -68.4(6) . . . . ? C4 C5 C6 N3 70.9(5) . . . . ? N3 C7 C8 C9A 78.0(6) . . . . ? N3 C7 C8 C9B 20.9(8) . . . . ? C7 C8 C9A N1 -83.0(6) . . . . ? C9B C8 C9A N1 36.8(5) . . . . ? C9A C8 C9B N1 -38.8(5) . . . . ? C7 C8 C9B N1 47.2(7) . . . . ? N1 C10B C11 C10B -136.2(6) . . . 2 ? N1 C10B C11 C10A 175.4(5) . . . 2 ? N1 C10B C11 C10A -47.0(6) . . . . ? N1 C10A C11 C10B 172.8(6) . . . 2 ? N1 C10A C11 C10B 52.2(6) . . . . ? N1 C10A C11 C10A 126.7(6) . . . 2 ? C11 C10A N1 C9B -124.1(6) . . . . ? C11 C10A N1 C1A 178.4(5) . . . . ? C11 C10A N1 C10B -50.7(6) . . . . ? C11 C10A N1 C9A -65.9(7) . . . . ? C11 C10A N1 C1B 147.3(7) . . . . ? C11 C10A N1 Ni1 50.7(7) . . . . ? C8 C9B N1 C10A 115.5(6) . . . . ? C8 C9B N1 C1A -153.3(7) . . . . ? C8 C9B N1 C10B 74.9(6) . . . . ? C8 C9B N1 C9A 32.6(4) . . . . ? C8 C9B N1 C1B -175.6(5) . . . . ? C8 C9B N1 Ni1 -59.4(5) . . . . ? C2 C1A N1 C10A -61.7(6) . . . . ? C2 C1A N1 C9B 176.5(7) . . . . ? C2 C1A N1 C10B -104.3(6) . . . . ? C2 C1A N1 C9A -178.4(4) . . . . ? C2 C1A N1 C1B -28.8(4) . . . . ? C2 C1A N1 Ni1 70.2(5) . . . . ? C11 C10B N1 C10A 48.3(6) . . . . ? C11 C10B N1 C9B 176.2(6) . . . . ? C11 C10B N1 C1A 122.8(6) . . . . ? C11 C10B N1 C9A -147.4(7) . . . . ? C11 C10B N1 C1B 64.9(6) . . . . ? C11 C10B N1 Ni1 -51.2(7) . . . . ? C8 C9A N1 C10A -170.1(5) . . . . ? C8 C9A N1 C9B -43.1(6) . . . . ? C8 C9A N1 C1A -47.8(7) . . . . ? C8 C9A N1 C10B 179.5(7) . . . . ? C8 C9A N1 C1B -102.1(8) . . . . ? C8 C9A N1 Ni1 65.8(6) . . . . ? C2 C1B N1 C10A -178.7(7) . . . . ? C2 C1B N1 C9B 54.2(7) . . . . ? C2 C1B N1 C1A 34.4(5) . . . . ? C2 C1B N1 C10B 169.6(5) . . . . ? C2 C1B N1 C9A 100.9(8) . . . . ? C2 C1B N1 Ni1 -66.9(6) . . . . ? N2 Ni1 N1 C10A 108.2(4) . . . . ? N3 Ni1 N1 C10A -155.1(4) . . . . ? O20 Ni1 N1 C10A 18.6(4) . . . . ? O25 Ni1 N1 C10A -68.5(4) . . . . ? O21 Ni1 N1 C10A 18.3(6) . . . . ? N2 Ni1 N1 C9B -76.1(4) . . . . ? N3 Ni1 N1 C9B 20.5(4) . . . . ? O20 Ni1 N1 C9B -165.8(4) . . . . ? O25 Ni1 N1 C9B 107.1(4) . . . . ? O21 Ni1 N1 C9B -166.1(4) . . . . ? N2 Ni1 N1 C1A -22.8(4) . . . . ? N3 Ni1 N1 C1A 73.9(3) . . . . ? O20 Ni1 N1 C1A -112.4(3) . . . . ? O25 Ni1 N1 C1A 160.5(3) . . . . ? O21 Ni1 N1 C1A -112.7(4) . . . . ? N2 Ni1 N1 C10B 152.8(4) . . . . ? N3 Ni1 N1 C10B -110.6(4) . . . . ? O20 Ni1 N1 C10B 63.1(4) . . . . ? O25 Ni1 N1 C10B -24.0(4) . . . . ? O21 Ni1 N1 C10B 62.8(6) . . . . ? N2 Ni1 N1 C9A -134.2(3) . . . . ? N3 Ni1 N1 C9A -37.6(3) . . . . ? O20 Ni1 N1 C9A 136.2(3) . . . . ? O25 Ni1 N1 C9A 49.1(3) . . . . ? O21 Ni1 N1 C9A 135.8(4) . . . . ? N2 Ni1 N1 C1B 39.1(3) . . . . ? N3 Ni1 N1 C1B 135.8(3) . . . . ? O20 Ni1 N1 C1B -50.5(3) . . . . ? O25 Ni1 N1 C1B -137.6(3) . . . . ? O21 Ni1 N1 C1B -50.8(5) . . . . ? C5 C4 N2 C3 166.8(4) . . . . ? C5 C4 N2 Ni1 30.4(6) . . . . ? C2 C3 N2 C4 -78.1(5) . . . . ? C2 C3 N2 Ni1 63.0(5) . . . . ? N3 Ni1 N2 C4 -0.9(3) . . . . ? N1 Ni1 N2 C4 96.4(3) . . . . ? O20 Ni1 N2 C4 -160.8(3) . . . . ? O25 Ni1 N2 C4 -98.9(6) . . . . ? O21 Ni1 N2 C4 -100.2(3) . . . . ? N3 Ni1 N2 C3 -137.5(3) . . . . ? N1 Ni1 N2 C3 -40.2(3) . . . . ? O20 Ni1 N2 C3 62.6(3) . . . . ? O25 Ni1 N2 C3 124.5(5) . . . . ? O21 Ni1 N2 C3 123.1(3) . . . . ? C5 C6 N3 C7 -169.3(5) . . . . ? C5 C6 N3 Ni1 -34.3(5) . . . . ? C8 C7 N3 C6 76.7(6) . . . . ? C8 C7 N3 Ni1 -61.9(5) . . . . ? N2 Ni1 N3 C6 2.6(4) . . . . ? N1 Ni1 N3 C6 -93.8(3) . . . . ? O20 Ni1 N3 C6 104.0(4) . . . . ? O25 Ni1 N3 C6 170.3(3) . . . . ? O21 Ni1 N3 C6 88.1(3) . . . . ? N2 Ni1 N3 C7 137.6(3) . . . . ? N1 Ni1 N3 C7 41.3(3) . . . . ? O20 Ni1 N3 C7 -121.0(4) . . . . ? O25 Ni1 N3 C7 -54.6(3) . . . . ? O21 Ni1 N3 C7 -136.8(3) . . . . ? O21 C20 O20 Ni1 0.4(3) . . . . ? C21 C20 O20 Ni1 -179.3(3) . . . . ? N2 Ni1 O20 C20 84.5(2) . . . . ? N3 Ni1 O20 C20 -18.2(5) . . . . ? N1 Ni1 O20 C20 179.9(2) . . . . ? O25 Ni1 O20 C20 -84.6(2) . . . . ? O21 Ni1 O20 C20 -0.20(19) . . . . ? O20 C20 O21 Ni1 -0.3(3) . . . . ? C21 C20 O21 Ni1 179.3(3) . . . . ? N2 Ni1 O21 C20 -91.0(2) . . . . ? N3 Ni1 O21 C20 173.9(2) . . . . ? N1 Ni1 O21 C20 0.6(5) . . . . ? O20 Ni1 O21 C20 0.2(2) . . . . ? O25 Ni1 O21 C20 89.3(2) . . . . ? F22 C22 S22 O24 -72.4(5) . . . . ? F23 C22 S22 O24 52.1(5) . . . . ? F24 C22 S22 O24 170.6(4) . . . . ? F22 C22 S22 O23 168.7(4) . . . . ? F23 C22 S22 O23 -66.7(5) . . . . ? F24 C22 S22 O23 51.7(4) . . . . ? F22 C22 S22 O22 49.5(5) . . . . ? F23 C22 S22 O22 174.0(4) . . . . ? F24 C22 S22 O22 -67.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 30.47 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 1.001 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.105 # Attachment 'web_deposit_cif_file_2_BernhardSpingler_1312475891.2.cif' data_am110304 _database_code_depnum_ccdc_archive 'CCDC 661094' #TrackingRef 'web_deposit_cif_file_2_BernhardSpingler_1312475891.2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23.50 H49 Cl Cu2 F6 N6 O7.50 S2' _chemical_formula_weight 876.34 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 11.6587(9) _cell_length_b 11.9119(10) _cell_length_c 13.8305(11) _cell_angle_alpha 97.909(10) _cell_angle_beta 96.699(9) _cell_angle_gamma 104.467(9) _cell_volume 1819.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 7998 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 906 _exptl_absorpt_coefficient_mu 1.437 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7719 _exptl_absorpt_correction_T_max 0.9008 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '/f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 11 _diffrn_standards_decay_% ? _diffrn_reflns_number 33110 _diffrn_reflns_av_R_equivalents 0.0960 _diffrn_reflns_av_sigmaI/netI 0.0774 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 30.51 _reflns_number_total 10097 _reflns_number_gt 6276 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _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^)+(0.0814P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10097 _refine_ls_number_parameters 435 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1516 _refine_ls_wR_factor_gt 0.1312 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.974 _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 Cu1 Cu 0.59089(4) -0.17510(3) 0.28043(3) 0.03363(11) Uani 1 1 d . . . Cu2 Cu 0.80769(3) 0.05143(3) 0.27029(3) 0.03270(11) Uani 1 1 d . . . F30 F 0.3230(3) 0.1624(3) 0.2363(3) 0.0925(10) Uani 1 1 d . . . F31 F 0.2834(4) 0.2330(4) 0.1076(4) 0.1139(14) Uani 1 1 d . . . F32 F 0.4596(3) 0.2976(2) 0.1968(3) 0.0993(12) Uani 1 1 d . . . F40 F -0.0263(3) 0.5470(2) 0.3631(3) 0.0848(10) Uani 1 1 d . . . F41 F 0.0369(3) 0.5773(3) 0.2279(2) 0.0912(11) Uani 1 1 d . . . F42 F 0.1226(2) 0.69272(19) 0.36193(19) 0.0566(6) Uani 1 1 d . . . S30 S 0.41993(10) 0.08987(9) 0.08663(8) 0.0536(3) Uani 1 1 d . . . S40 S 0.17289(8) 0.48672(8) 0.34096(7) 0.0449(2) Uani 1 1 d . . . Cl1 Cl 0.72260(8) -0.02371(7) 0.41246(6) 0.03975(18) Uani 1 1 d . . . C1 C 0.5458(4) -0.4218(3) 0.1791(3) 0.0477(9) Uani 1 1 d . . . H1A H 0.4829 -0.4547 0.2176 0.057 Uiso 1 1 calc R . . H1B H 0.5749 -0.4877 0.1491 0.057 Uiso 1 1 calc R . . C2 C 0.4885(4) -0.3713(3) 0.0958(3) 0.0509(9) Uani 1 1 d . . . H2A H 0.5525 -0.3120 0.0751 0.061 Uiso 1 1 calc R . . H2B H 0.4547 -0.4357 0.0385 0.061 Uiso 1 1 calc R . . C3 C 0.3895(4) -0.3141(3) 0.1207(3) 0.0501(9) Uani 1 1 d . . . H3A H 0.3446 -0.3050 0.0582 0.060 Uiso 1 1 calc R . . H3B H 0.3329 -0.3678 0.1528 0.060 Uiso 1 1 calc R . . C4 C 0.3363(3) -0.1654(3) 0.2397(3) 0.0466(8) Uani 1 1 d . . . H4A H 0.2780 -0.2385 0.2475 0.056 Uiso 1 1 calc R . . H4B H 0.2928 -0.1219 0.1994 0.056 Uiso 1 1 calc R . . C5 C 0.3882(4) -0.0901(3) 0.3413(3) 0.0466(8) Uani 1 1 d . . . H5A H 0.3272 -0.0531 0.3651 0.056 Uiso 1 1 calc R . . H5B H 0.4582 -0.0262 0.3347 0.056 Uiso 1 1 calc R . . C6 C 0.4275(3) -0.1595(3) 0.4184(3) 0.0436(8) Uani 1 1 d . . . H6A H 0.4828 -0.1042 0.4744 0.052 Uiso 1 1 calc R . . H6B H 0.3563 -0.2018 0.4443 0.052 Uiso 1 1 calc R . . C7 C 0.5488(4) -0.2981(3) 0.4521(3) 0.0487(9) Uani 1 1 d . . . H7A H 0.4941 -0.3190 0.5003 0.058 Uiso 1 1 calc R . . H7B H 0.6221 -0.2386 0.4879 0.058 Uiso 1 1 calc R . . C8 C 0.5822(4) -0.4075(3) 0.4069(3) 0.0513(10) Uani 1 1 d . . . H8A H 0.6111 -0.4444 0.4613 0.062 Uiso 1 1 calc R . . H8B H 0.5086 -0.4644 0.3686 0.062 Uiso 1 1 calc R . . C9 C 0.6772(4) -0.3876(3) 0.3394(3) 0.0511(9) Uani 1 1 d . . . H9A H 0.7523 -0.3348 0.3790 0.061 Uiso 1 1 calc R . . H9B H 0.6932 -0.4641 0.3173 0.061 Uiso 1 1 calc R . . C10 C 0.7562(4) -0.3138(3) 0.1986(3) 0.0496(9) Uani 1 1 d . . . H10A H 0.7347 -0.2910 0.1341 0.059 Uiso 1 1 calc R . . H10B H 0.7808 -0.3875 0.1855 0.059 Uiso 1 1 calc R . . C11 C 0.8629(3) -0.2164(3) 0.2596(3) 0.0463(9) Uani 1 1 d . . . H11A H 0.9190 -0.2532 0.2943 0.056 Uiso 1 1 calc R . . H11B H 0.8331 -0.1687 0.3103 0.056 Uiso 1 1 calc R . . C12 C 0.9310(4) -0.1348(3) 0.1955(3) 0.0477(9) Uani 1 1 d . . . H12A H 1.0044 -0.1585 0.1833 0.057 Uiso 1 1 calc R . . H12B H 0.8800 -0.1452 0.1308 0.057 Uiso 1 1 calc R . . C13 C 1.0551(4) 0.0094(4) 0.3339(3) 0.0506(9) Uani 1 1 d . . . H13A H 1.1268 -0.0125 0.3145 0.061 Uiso 1 1 calc R . . H13B H 1.0196 -0.0463 0.3762 0.061 Uiso 1 1 calc R . . C14 C 1.0962(3) 0.1329(3) 0.3959(3) 0.0495(9) Uani 1 1 d . . . H14A H 1.1574 0.1330 0.4519 0.059 Uiso 1 1 calc R . . H14B H 1.1357 0.1880 0.3547 0.059 Uiso 1 1 calc R . . C15 C 0.9989(3) 0.1804(4) 0.4373(3) 0.0481(9) Uani 1 1 d . . . H15A H 0.9564 0.1247 0.4767 0.058 Uiso 1 1 calc R . . H15B H 1.0365 0.2565 0.4820 0.058 Uiso 1 1 calc R . . C16 C 0.8325(4) 0.2680(3) 0.3966(3) 0.0461(8) Uani 1 1 d . . . H16A H 0.8804 0.3507 0.4190 0.055 Uiso 1 1 calc R . . H16B H 0.8021 0.2376 0.4545 0.055 Uiso 1 1 calc R . . C17 C 0.7254(4) 0.2642(3) 0.3186(3) 0.0482(9) Uani 1 1 d . . . H17A H 0.6623 0.1900 0.3152 0.058 Uiso 1 1 calc R . . H17B H 0.6915 0.3303 0.3399 0.058 Uiso 1 1 calc R . . C18 C 0.7582(4) 0.2721(3) 0.2159(3) 0.0459(8) Uani 1 1 d . . . H18A H 0.6917 0.2881 0.1734 0.055 Uiso 1 1 calc R . . H18B H 0.8305 0.3386 0.2206 0.055 Uiso 1 1 calc R . . C19 C 0.8787(3) 0.1830(3) 0.1074(3) 0.0432(8) Uani 1 1 d . . . H19A H 0.9430 0.2532 0.1416 0.052 Uiso 1 1 calc R . . H19B H 0.8455 0.2015 0.0441 0.052 Uiso 1 1 calc R . . C20 C 0.9340(3) 0.0799(3) 0.0847(3) 0.0430(8) Uani 1 1 d . . . H20A H 0.9763 0.0912 0.0273 0.052 Uiso 1 1 calc R . . H20B H 0.8682 0.0063 0.0652 0.052 Uiso 1 1 calc R . . C21 C 1.0227(3) 0.0641(3) 0.1704(3) 0.0415(7) Uani 1 1 d . . . H21A H 1.0806 0.0260 0.1420 0.050 Uiso 1 1 calc R . . H21B H 1.0686 0.1429 0.2071 0.050 Uiso 1 1 calc R . . C30 C 0.3707(4) 0.2016(4) 0.1592(4) 0.0646(12) Uani 1 1 d . . . C40 C 0.0712(3) 0.5799(3) 0.3231(3) 0.0452(8) Uani 1 1 d . . . N1 N 0.6483(3) -0.3361(2) 0.2494(2) 0.0418(7) Uani 1 1 d . . . N2 N 0.4325(3) -0.1966(2) 0.1866(2) 0.0395(6) Uani 1 1 d . . . H2 H 0.4501 -0.1419 0.1449 0.047 Uiso 1 1 calc R . . N3 N 0.4893(3) -0.2469(2) 0.3747(2) 0.0377(6) Uani 1 1 d . . . H3 H 0.4289 -0.3089 0.3366 0.045 Uiso 1 1 calc R . . N4 N 0.9658(2) -0.0074(2) 0.2419(2) 0.0386(6) Uani 1 1 d . . . N5 N 0.9109(3) 0.1975(2) 0.3580(2) 0.0379(6) Uani 1 1 d . . . H5 H 0.9554 0.2412 0.3177 0.045 Uiso 1 1 calc R . . N6 N 0.7822(3) 0.1604(2) 0.1693(2) 0.0374(6) Uani 1 1 d . . . H6 H 0.7126 0.1193 0.1260 0.045 Uiso 1 1 calc R . . O1 O 0.6893(2) -0.08756(19) 0.19696(19) 0.0374(5) Uani 1 1 d . . . H1 H 0.653(4) -0.078(4) 0.148(3) 0.045 Uiso 1 1 d . . . O30 O 0.3130(4) -0.0060(4) 0.0550(4) 0.0981(15) Uani 1 1 d . . . O31 O 0.5073(3) 0.0643(2) 0.1560(2) 0.0529(7) Uani 1 1 d . . . O32 O 0.4664(6) 0.1462(4) 0.0099(3) 0.1095(17) Uani 1 1 d . . . O40 O 0.1922(5) 0.4927(4) 0.4458(3) 0.1038(16) Uani 1 1 d . . . O41 O 0.1032(3) 0.3742(2) 0.2857(3) 0.0671(9) Uani 1 1 d . . . O42 O 0.2749(3) 0.5419(3) 0.2991(3) 0.0690(9) Uani 1 1 d . . . O50 O 0.0712(11) 0.5155(11) 0.0020(10) 0.136(4) Uiso 0.50 1 d PD . . C52 C 0.1214(17) 0.4139(15) 0.0324(14) 0.128(6) Uiso 0.50 1 d PD . . 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 Cu1 0.0310(2) 0.03206(19) 0.0386(2) 0.00981(14) 0.00671(16) 0.00747(14) Cu2 0.0296(2) 0.03195(19) 0.0357(2) 0.00754(14) 0.00400(16) 0.00636(14) F30 0.083(2) 0.101(2) 0.102(2) 0.015(2) 0.047(2) 0.0262(18) F31 0.097(3) 0.120(3) 0.155(4) 0.042(3) 0.020(3) 0.074(2) F32 0.077(2) 0.0466(15) 0.166(4) -0.0100(18) 0.036(2) 0.0089(14) F40 0.0521(15) 0.0586(16) 0.156(3) 0.0311(17) 0.0461(19) 0.0168(12) F41 0.119(3) 0.103(2) 0.0560(15) -0.0053(15) -0.0232(17) 0.066(2) F42 0.0544(14) 0.0407(11) 0.0717(15) 0.0031(10) 0.0096(12) 0.0108(10) S30 0.0599(6) 0.0564(6) 0.0464(5) 0.0100(4) -0.0007(5) 0.0228(5) S40 0.0401(5) 0.0411(4) 0.0531(5) 0.0093(4) 0.0065(4) 0.0101(3) Cl1 0.0367(4) 0.0408(4) 0.0387(4) 0.0105(3) 0.0053(3) 0.0032(3) C1 0.048(2) 0.0327(16) 0.059(2) 0.0042(14) 0.0101(18) 0.0063(14) C2 0.052(2) 0.0440(19) 0.052(2) 0.0007(15) 0.0090(19) 0.0080(16) C3 0.046(2) 0.050(2) 0.048(2) 0.0043(16) 0.0009(18) 0.0060(16) C4 0.0390(18) 0.0457(19) 0.054(2) 0.0108(15) 0.0052(17) 0.0099(15) C5 0.0403(19) 0.0430(18) 0.058(2) 0.0069(15) 0.0112(17) 0.0136(15) C6 0.0370(18) 0.0456(18) 0.0472(19) 0.0062(14) 0.0140(16) 0.0069(14) C7 0.045(2) 0.052(2) 0.049(2) 0.0198(16) 0.0030(17) 0.0083(16) C8 0.049(2) 0.0439(19) 0.065(2) 0.0296(17) 0.0082(19) 0.0088(16) C9 0.044(2) 0.0422(19) 0.073(3) 0.0236(17) 0.0100(19) 0.0139(15) C10 0.048(2) 0.0330(16) 0.071(3) 0.0106(16) 0.019(2) 0.0128(15) C11 0.0358(17) 0.0379(17) 0.071(2) 0.0154(16) 0.0131(18) 0.0149(14) C12 0.0384(18) 0.0418(18) 0.066(2) 0.0106(16) 0.0158(18) 0.0126(14) C13 0.0368(18) 0.058(2) 0.061(2) 0.0258(18) 0.0052(18) 0.0139(16) C14 0.0328(17) 0.056(2) 0.055(2) 0.0228(17) -0.0098(16) 0.0036(15) C15 0.0396(19) 0.057(2) 0.0400(18) 0.0125(15) 0.0021(16) -0.0005(16) C16 0.050(2) 0.0355(17) 0.0472(19) -0.0005(14) 0.0139(17) 0.0022(14) C17 0.047(2) 0.0429(19) 0.058(2) 0.0087(16) 0.0161(19) 0.0164(16) C18 0.045(2) 0.0423(18) 0.055(2) 0.0140(15) 0.0124(18) 0.0149(15) C19 0.0432(19) 0.0431(18) 0.0430(18) 0.0130(14) 0.0060(16) 0.0087(14) C20 0.0397(18) 0.0445(18) 0.0441(18) 0.0086(14) 0.0118(16) 0.0075(14) C21 0.0303(16) 0.0441(18) 0.0514(19) 0.0091(14) 0.0126(16) 0.0091(13) C30 0.050(2) 0.056(2) 0.089(3) 0.018(2) 0.017(3) 0.0121(19) C40 0.0371(18) 0.0453(19) 0.052(2) 0.0073(15) 0.0054(17) 0.0095(14) N1 0.0390(15) 0.0326(14) 0.0553(17) 0.0125(12) 0.0103(14) 0.0086(11) N2 0.0356(15) 0.0399(14) 0.0426(15) 0.0112(11) 0.0043(13) 0.0084(11) N3 0.0344(14) 0.0357(13) 0.0414(14) 0.0099(11) 0.0071(12) 0.0041(11) N4 0.0292(13) 0.0404(14) 0.0481(16) 0.0137(12) 0.0074(12) 0.0089(11) N5 0.0359(14) 0.0371(14) 0.0367(13) 0.0073(10) 0.0033(12) 0.0033(11) N6 0.0340(14) 0.0373(14) 0.0411(14) 0.0108(11) 0.0047(12) 0.0082(11) O1 0.0346(12) 0.0304(10) 0.0455(13) 0.0077(9) 0.0110(10) 0.0032(9) O30 0.079(3) 0.075(2) 0.117(3) -0.011(2) -0.041(3) 0.020(2) O31 0.0465(15) 0.0540(15) 0.0568(16) 0.0114(12) -0.0003(13) 0.0138(12) O32 0.183(5) 0.111(3) 0.082(3) 0.054(2) 0.061(3) 0.088(3) O40 0.152(4) 0.132(4) 0.056(2) 0.020(2) 0.005(2) 0.093(3) O41 0.0472(16) 0.0391(14) 0.109(3) 0.0038(15) 0.0165(18) 0.0037(12) O42 0.0438(15) 0.0435(15) 0.119(3) 0.0148(16) 0.0295(18) 0.0031(12) _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 Cu1 O1 1.944(2) . ? Cu1 N3 1.999(3) . ? Cu1 N2 2.067(3) . ? Cu1 N1 2.189(3) . ? Cu1 Cl1 2.4496(9) . ? Cu2 O1 1.935(2) . ? Cu2 N5 1.995(3) . ? Cu2 N6 2.078(3) . ? Cu2 N4 2.187(3) . ? Cu2 Cl1 2.4793(10) . ? F30 C30 1.345(6) . ? F31 C30 1.334(6) . ? F32 C30 1.331(5) . ? F40 C40 1.317(5) . ? F41 C40 1.325(5) . ? F42 C40 1.333(4) . ? S30 O32 1.421(4) . ? S30 O31 1.434(3) . ? S30 O30 1.440(4) . ? S30 C30 1.805(5) . ? S40 O40 1.430(4) . ? S40 O42 1.433(3) . ? S40 O41 1.438(3) . ? S40 C40 1.834(4) . ? C1 N1 1.504(5) . ? C1 C2 1.532(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.528(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.494(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.503(5) . ? C4 C5 1.526(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.533(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N3 1.507(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N3 1.489(4) . ? C7 C8 1.526(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.524(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N1 1.502(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N1 1.496(5) . ? C10 C11 1.539(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.542(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N4 1.497(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N4 1.503(5) . ? C13 C14 1.528(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.523(6) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N5 1.483(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N5 1.484(5) . ? C16 C17 1.539(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.523(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N6 1.502(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 N6 1.486(5) . ? C19 C20 1.537(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.543(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 N4 1.499(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? N2 H2 0.9300 . ? N3 H3 0.9300 . ? N5 H5 0.9300 . ? N6 H6 0.9300 . ? O1 H1 0.80(4) . ? O50 C52 1.556(15) . ? O50 O50 1.60(2) 2_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 O1 Cu1 N3 173.29(11) . . ? O1 Cu1 N2 93.75(11) . . ? N3 Cu1 N2 86.66(12) . . ? O1 Cu1 N1 96.16(11) . . ? N3 Cu1 N1 90.08(12) . . ? N2 Cu1 N1 107.76(11) . . ? O1 Cu1 Cl1 82.71(8) . . ? N3 Cu1 Cl1 92.45(8) . . ? N2 Cu1 Cl1 137.34(9) . . ? N1 Cu1 Cl1 114.89(8) . . ? O1 Cu2 N5 171.47(12) . . ? O1 Cu2 N6 95.64(11) . . ? N5 Cu2 N6 85.84(11) . . ? O1 Cu2 N4 96.75(11) . . ? N5 Cu2 N4 90.82(12) . . ? N6 Cu2 N4 107.12(12) . . ? O1 Cu2 Cl1 82.09(8) . . ? N5 Cu2 Cl1 91.41(9) . . ? N6 Cu2 Cl1 140.47(9) . . ? N4 Cu2 Cl1 112.35(8) . . ? O32 S30 O31 115.2(3) . . ? O32 S30 O30 115.1(3) . . ? O31 S30 O30 113.4(2) . . ? O32 S30 C30 103.5(3) . . ? O31 S30 C30 103.3(2) . . ? O30 S30 C30 104.2(3) . . ? O40 S40 O42 115.8(3) . . ? O40 S40 O41 114.8(3) . . ? O42 S40 O41 114.6(2) . . ? O40 S40 C40 103.2(2) . . ? O42 S40 C40 103.38(19) . . ? O41 S40 C40 102.38(18) . . ? Cu1 Cl1 Cu2 82.06(3) . . ? N1 C1 C2 115.6(3) . . ? N1 C1 H1A 108.4 . . ? C2 C1 H1A 108.4 . . ? N1 C1 H1B 108.4 . . ? C2 C1 H1B 108.4 . . ? H1A C1 H1B 107.4 . . ? C3 C2 C1 115.9(4) . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2B 108.3 . . ? C1 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? N2 C3 C2 114.9(3) . . ? N2 C3 H3A 108.6 . . ? C2 C3 H3A 108.6 . . ? N2 C3 H3B 108.6 . . ? C2 C3 H3B 108.6 . . ? H3A C3 H3B 107.5 . . ? N2 C4 C5 111.7(3) . . ? N2 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N2 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C4 C5 C6 113.6(3) . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? N3 C6 C5 111.3(3) . . ? N3 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? N3 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N3 C7 C8 111.3(3) . . ? N3 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? N3 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C9 C8 C7 116.0(3) . . ? C9 C8 H8A 108.3 . . ? C7 C8 H8A 108.3 . . ? C9 C8 H8B 108.3 . . ? C7 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? N1 C9 C8 116.7(3) . . ? N1 C9 H9A 108.1 . . ? C8 C9 H9A 108.1 . . ? N1 C9 H9B 108.1 . . ? C8 C9 H9B 108.1 . . ? H9A C9 H9B 107.3 . . ? N1 C10 C11 112.8(3) . . ? N1 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? N1 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12 112.7(4) . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? N4 C12 C11 113.2(3) . . ? N4 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? N4 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? N4 C13 C14 116.4(3) . . ? N4 C13 H13A 108.2 . . ? C14 C13 H13A 108.2 . . ? N4 C13 H13B 108.2 . . ? C14 C13 H13B 108.2 . . ? H13A C13 H13B 107.3 . . ? C15 C14 C13 116.2(3) . . ? C15 C14 H14A 108.2 . . ? C13 C14 H14A 108.2 . . ? C15 C14 H14B 108.2 . . ? C13 C14 H14B 108.2 . . ? H14A C14 H14B 107.4 . . ? N5 C15 C14 112.0(3) . . ? N5 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? N5 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? N5 C16 C17 112.5(3) . . ? N5 C16 H16A 109.1 . . ? C17 C16 H16A 109.1 . . ? N5 C16 H16B 109.1 . . ? C17 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C16 113.4(3) . . ? C18 C17 H17A 108.9 . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17B 108.9 . . ? C16 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? N6 C18 C17 111.5(3) . . ? N6 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? N6 C18 H18B 109.3 . . ? C17 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? N6 C19 C20 114.2(3) . . ? N6 C19 H19A 108.7 . . ? C20 C19 H19A 108.7 . . ? N6 C19 H19B 108.7 . . ? C20 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C19 C20 C21 115.4(3) . . ? C19 C20 H20A 108.4 . . ? C21 C20 H20A 108.4 . . ? C19 C20 H20B 108.4 . . ? C21 C20 H20B 108.4 . . ? H20A C20 H20B 107.5 . . ? N4 C21 C20 114.8(3) . . ? N4 C21 H21A 108.6 . . ? C20 C21 H21A 108.6 . . ? N4 C21 H21B 108.6 . . ? C20 C21 H21B 108.6 . . ? H21A C21 H21B 107.5 . . ? F32 C30 F31 108.8(4) . . ? F32 C30 F30 106.4(5) . . ? F31 C30 F30 104.8(4) . . ? F32 C30 S30 112.7(3) . . ? F31 C30 S30 112.1(4) . . ? F30 C30 S30 111.5(3) . . ? F40 C40 F41 107.6(4) . . ? F40 C40 F42 106.9(3) . . ? F41 C40 F42 106.0(3) . . ? F40 C40 S40 112.4(3) . . ? F41 C40 S40 111.0(3) . . ? F42 C40 S40 112.5(2) . . ? C10 N1 C9 108.3(3) . . ? C10 N1 C1 108.4(3) . . ? C9 N1 C1 110.2(3) . . ? C10 N1 Cu1 110.4(2) . . ? C9 N1 Cu1 114.1(2) . . ? C1 N1 Cu1 105.4(2) . . ? C3 N2 C4 112.6(3) . . ? C3 N2 Cu1 113.5(2) . . ? C4 N2 Cu1 112.8(2) . . ? C3 N2 H2 105.7 . . ? C4 N2 H2 105.7 . . ? Cu1 N2 H2 105.7 . . ? C7 N3 C6 111.9(3) . . ? C7 N3 Cu1 116.7(2) . . ? C6 N3 Cu1 109.1(2) . . ? C7 N3 H3 106.1 . . ? C6 N3 H3 106.1 . . ? Cu1 N3 H3 106.1 . . ? C12 N4 C21 108.7(3) . . ? C12 N4 C13 108.3(3) . . ? C21 N4 C13 109.5(3) . . ? C12 N4 Cu2 111.0(2) . . ? C21 N4 Cu2 106.5(2) . . ? C13 N4 Cu2 112.8(2) . . ? C15 N5 C16 112.6(3) . . ? C15 N5 Cu2 116.0(2) . . ? C16 N5 Cu2 108.5(2) . . ? C15 N5 H5 106.4 . . ? C16 N5 H5 106.4 . . ? Cu2 N5 H5 106.4 . . ? C19 N6 C18 112.2(3) . . ? C19 N6 Cu2 113.4(2) . . ? C18 N6 Cu2 113.0(2) . . ? C19 N6 H6 105.8 . . ? C18 N6 H6 105.8 . . ? Cu2 N6 H6 105.8 . . ? Cu2 O1 Cu1 113.05(13) . . ? Cu2 O1 H1 115(3) . . ? Cu1 O1 H1 114(3) . . ? C52 O50 O50 111.2(14) . 2_565 ? 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 O1 Cu1 Cl1 Cu2 2.00(8) . . . . ? N3 Cu1 Cl1 Cu2 -173.35(9) . . . . ? N2 Cu1 Cl1 Cu2 -85.62(13) . . . . ? N1 Cu1 Cl1 Cu2 95.43(10) . . . . ? O1 Cu2 Cl1 Cu1 -2.01(8) . . . . ? N5 Cu2 Cl1 Cu1 172.45(9) . . . . ? N6 Cu2 Cl1 Cu1 87.27(12) . . . . ? N4 Cu2 Cl1 Cu1 -96.09(8) . . . . ? N1 C1 C2 C3 -86.3(4) . . . . ? C1 C2 C3 N2 73.8(4) . . . . ? N2 C4 C5 C6 -74.5(4) . . . . ? C4 C5 C6 N3 40.9(4) . . . . ? N3 C7 C8 C9 65.7(4) . . . . ? C7 C8 C9 N1 -60.3(5) . . . . ? N1 C10 C11 C12 -139.8(3) . . . . ? C10 C11 C12 N4 138.1(3) . . . . ? N4 C13 C14 C15 60.9(5) . . . . ? C13 C14 C15 N5 -65.2(4) . . . . ? N5 C16 C17 C18 -41.0(4) . . . . ? C16 C17 C18 N6 72.2(4) . . . . ? N6 C19 C20 C21 -76.5(4) . . . . ? C19 C20 C21 N4 85.7(4) . . . . ? O32 S30 C30 F32 -60.5(5) . . . . ? O31 S30 C30 F32 60.0(4) . . . . ? O30 S30 C30 F32 178.8(4) . . . . ? O32 S30 C30 F31 62.6(5) . . . . ? O31 S30 C30 F31 -176.9(4) . . . . ? O30 S30 C30 F31 -58.1(4) . . . . ? O32 S30 C30 F30 179.8(4) . . . . ? O31 S30 C30 F30 -59.7(4) . . . . ? O30 S30 C30 F30 59.1(4) . . . . ? O40 S40 C40 F40 -54.9(4) . . . . ? O42 S40 C40 F40 -176.0(3) . . . . ? O41 S40 C40 F40 64.6(3) . . . . ? O40 S40 C40 F41 -175.5(4) . . . . ? O42 S40 C40 F41 63.4(4) . . . . ? O41 S40 C40 F41 -56.0(4) . . . . ? O40 S40 C40 F42 65.9(4) . . . . ? O42 S40 C40 F42 -55.2(3) . . . . ? O41 S40 C40 F42 -174.6(3) . . . . ? C11 C10 N1 C9 -67.0(4) . . . . ? C11 C10 N1 C1 173.5(3) . . . . ? C11 C10 N1 Cu1 58.5(4) . . . . ? C8 C9 N1 C10 175.0(3) . . . . ? C8 C9 N1 C1 -66.6(4) . . . . ? C8 C9 N1 Cu1 51.7(4) . . . . ? C2 C1 N1 C10 -74.9(4) . . . . ? C2 C1 N1 C9 166.8(4) . . . . ? C2 C1 N1 Cu1 43.3(4) . . . . ? O1 Cu1 N1 C10 12.8(3) . . . . ? N3 Cu1 N1 C10 -164.7(3) . . . . ? N2 Cu1 N1 C10 108.7(2) . . . . ? Cl1 Cu1 N1 C10 -72.0(3) . . . . ? O1 Cu1 N1 C9 135.0(2) . . . . ? N3 Cu1 N1 C9 -42.6(2) . . . . ? N2 Cu1 N1 C9 -129.1(2) . . . . ? Cl1 Cu1 N1 C9 50.2(3) . . . . ? O1 Cu1 N1 C1 -104.0(2) . . . . ? N3 Cu1 N1 C1 78.4(2) . . . . ? N2 Cu1 N1 C1 -8.1(3) . . . . ? Cl1 Cu1 N1 C1 171.2(2) . . . . ? C2 C3 N2 C4 -158.0(3) . . . . ? C2 C3 N2 Cu1 -28.3(4) . . . . ? C5 C4 N2 C3 148.2(3) . . . . ? C5 C4 N2 Cu1 18.1(4) . . . . ? O1 Cu1 N2 C3 98.9(3) . . . . ? N3 Cu1 N2 C3 -87.8(3) . . . . ? N1 Cu1 N2 C3 1.2(3) . . . . ? Cl1 Cu1 N2 C3 -177.8(2) . . . . ? O1 Cu1 N2 C4 -131.5(2) . . . . ? N3 Cu1 N2 C4 41.8(2) . . . . ? N1 Cu1 N2 C4 130.8(2) . . . . ? Cl1 Cu1 N2 C4 -48.2(3) . . . . ? C8 C7 N3 C6 165.2(3) . . . . ? C8 C7 N3 Cu1 -68.1(3) . . . . ? C5 C6 N3 C7 168.8(3) . . . . ? C5 C6 N3 Cu1 38.1(3) . . . . ? O1 Cu1 N3 C7 -106.9(10) . . . . ? N2 Cu1 N3 C7 159.4(3) . . . . ? N1 Cu1 N3 C7 51.6(3) . . . . ? Cl1 Cu1 N3 C7 -63.3(2) . . . . ? O1 Cu1 N3 C6 21.2(11) . . . . ? N2 Cu1 N3 C6 -72.5(2) . . . . ? N1 Cu1 N3 C6 179.7(2) . . . . ? Cl1 Cu1 N3 C6 64.8(2) . . . . ? C11 C12 N4 C21 -175.7(3) . . . . ? C11 C12 N4 C13 65.4(4) . . . . ? C11 C12 N4 Cu2 -58.9(3) . . . . ? C20 C21 N4 C12 76.4(4) . . . . ? C20 C21 N4 C13 -165.5(3) . . . . ? C20 C21 N4 Cu2 -43.2(3) . . . . ? C14 C13 N4 C12 -176.3(3) . . . . ? C14 C13 N4 C21 65.3(4) . . . . ? C14 C13 N4 Cu2 -53.1(4) . . . . ? O1 Cu2 N4 C12 -10.3(3) . . . . ? N5 Cu2 N4 C12 165.8(2) . . . . ? N6 Cu2 N4 C12 -108.3(2) . . . . ? Cl1 Cu2 N4 C12 73.9(2) . . . . ? O1 Cu2 N4 C21 107.8(2) . . . . ? N5 Cu2 N4 C21 -76.1(2) . . . . ? N6 Cu2 N4 C21 9.8(2) . . . . ? Cl1 Cu2 N4 C21 -167.98(18) . . . . ? O1 Cu2 N4 C13 -132.0(2) . . . . ? N5 Cu2 N4 C13 44.1(2) . . . . ? N6 Cu2 N4 C13 130.0(2) . . . . ? Cl1 Cu2 N4 C13 -47.8(2) . . . . ? C14 C15 N5 C16 -167.0(3) . . . . ? C14 C15 N5 Cu2 67.1(3) . . . . ? C17 C16 N5 C15 -168.1(3) . . . . ? C17 C16 N5 Cu2 -38.3(3) . . . . ? O1 Cu2 N5 C15 100.7(8) . . . . ? N6 Cu2 N5 C15 -158.9(3) . . . . ? N4 Cu2 N5 C15 -51.8(3) . . . . ? Cl1 Cu2 N5 C15 60.6(3) . . . . ? O1 Cu2 N5 C16 -27.2(9) . . . . ? N6 Cu2 N5 C16 73.2(2) . . . . ? N4 Cu2 N5 C16 -179.7(2) . . . . ? Cl1 Cu2 N5 C16 -67.3(2) . . . . ? C20 C19 N6 C18 161.9(3) . . . . ? C20 C19 N6 Cu2 32.4(3) . . . . ? C17 C18 N6 C19 -144.9(3) . . . . ? C17 C18 N6 Cu2 -15.3(4) . . . . ? O1 Cu2 N6 C19 -103.7(2) . . . . ? N5 Cu2 N6 C19 84.7(2) . . . . ? N4 Cu2 N6 C19 -4.8(2) . . . . ? Cl1 Cu2 N6 C19 171.91(17) . . . . ? O1 Cu2 N6 C18 127.3(2) . . . . ? N5 Cu2 N6 C18 -44.3(2) . . . . ? N4 Cu2 N6 C18 -133.9(2) . . . . ? Cl1 Cu2 N6 C18 42.9(3) . . . . ? N5 Cu2 O1 Cu1 -37.9(8) . . . . ? N6 Cu2 O1 Cu1 -137.52(14) . . . . ? N4 Cu2 O1 Cu1 114.45(14) . . . . ? Cl1 Cu2 O1 Cu1 2.73(11) . . . . ? N3 Cu1 O1 Cu2 41.2(10) . . . . ? N2 Cu1 O1 Cu2 134.52(14) . . . . ? N1 Cu1 O1 Cu2 -117.15(14) . . . . ? Cl1 Cu1 O1 Cu2 -2.76(11) . . . . ? _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.908 _refine_diff_density_max 0.945 _refine_diff_density_min -0.565 _refine_diff_density_rms 0.103 # Attachment 'web_deposit_cif_file_4_BernhardSpingler_1312475891.3.cif' data_am130406 _database_code_depnum_ccdc_archive 'CCDC 661095' #TrackingRef 'web_deposit_cif_file_4_BernhardSpingler_1312475891.3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H33 N3 Ni O5' _chemical_formula_weight 394.15 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P21212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 15.612(2) _cell_length_b 15.6754(18) _cell_length_c 7.9380(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1942.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 7995 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 1.026 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7707 _exptl_absorpt_correction_T_max 0.8710 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '/f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 7.5 _diffrn_standards_decay_% ? _diffrn_reflns_number 42415 _diffrn_reflns_av_R_equivalents 0.0587 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 30.48 _reflns_number_total 5891 _reflns_number_gt 5493 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _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. One hydrogen atom of the water coordinated to the nickel metal could not be located. ; _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^)+(0.1133P)^2^+0.0979P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.152(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.025(15) _refine_ls_number_reflns 5891 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1513 _refine_ls_wR_factor_gt 0.1462 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 C8 C 0.8494(2) 0.1472(2) 0.2710(4) 0.0556(7) Uani 1 1 d . . . H8B H 0.8720 0.1463 0.1545 0.067 Uiso 1 1 calc R . . H8A H 0.8445 0.2077 0.3053 0.067 Uiso 1 1 calc R . . C6 C 0.91906(16) 0.20007(17) 0.6279(4) 0.0454(5) Uani 1 1 d . . . H6B H 0.8919 0.2437 0.5551 0.054 Uiso 1 1 calc R . . H6A H 0.9819 0.2068 0.6183 0.054 Uiso 1 1 calc R . . C2 C 0.63369(17) 0.22947(18) 0.6103(5) 0.0511(6) Uani 1 1 d . . . H2A H 0.6360 0.2918 0.6301 0.061 Uiso 1 1 calc R . . H2B H 0.5745 0.2154 0.5750 0.061 Uiso 1 1 calc R . . C21 C 0.9121(3) -0.0867(3) 1.0256(5) 0.0671(9) Uani 1 1 d . . . H21C H 0.9387 -0.1430 1.0127 0.081 Uiso 1 1 calc R . . H21B H 0.8599 -0.0921 1.0933 0.081 Uiso 1 1 calc R . . H21A H 0.9522 -0.0480 1.0821 0.081 Uiso 1 1 calc R . . C11 C 0.5694(3) 0.1031(3) 0.2502(6) 0.0769(12) Uani 1 1 d . . . H11A H 0.5982 0.0896 0.1438 0.092 Uiso 1 1 calc R . . H11B H 0.5613 0.1649 0.2590 0.092 Uiso 1 1 calc R . . H11C H 0.5135 0.0746 0.2536 0.092 Uiso 1 1 calc R . . O31 O 0.66943(18) -0.12880(15) 0.6056(5) 0.0731(8) Uani 1 1 d . . . C1 C 0.6947(2) 0.20810(19) 0.4625(4) 0.0508(6) Uani 1 1 d . . . H1A H 0.6722 0.2356 0.3593 0.061 Uiso 1 1 calc R . . H1B H 0.7513 0.2340 0.4865 0.061 Uiso 1 1 calc R . . O20 O 0.83914(13) 0.01091(12) 0.8506(3) 0.0461(4) Uani 1 1 d . . . C9 C 0.7592(2) 0.1084(2) 0.2691(4) 0.0569(7) Uani 1 1 d . . . H9A H 0.7266 0.1355 0.1765 0.068 Uiso 1 1 calc R . . H9B H 0.7645 0.0470 0.2416 0.068 Uiso 1 1 calc R . . N3 N 0.89462(13) 0.11350(14) 0.5657(3) 0.0408(4) Uani 1 1 d . . . H3C H 0.9343 0.0779 0.6175 0.049 Uiso 1 1 calc R . . C3 C 0.65132(17) 0.18461(18) 0.7769(4) 0.0473(5) Uani 1 1 d . . . H3A H 0.6341 0.2227 0.8705 0.057 Uiso 1 1 calc R . . H3B H 0.6156 0.1326 0.7835 0.057 Uiso 1 1 calc R . . N2 N 0.74236(13) 0.16048(13) 0.7994(3) 0.0393(4) Uani 1 1 d . . . H2C H 0.7419 0.1336 0.9038 0.047 Uiso 1 1 calc R . . C7 C 0.91461(19) 0.1042(2) 0.3853(4) 0.0507(6) Uani 1 1 d . . . H7A H 0.9173 0.0428 0.3571 0.061 Uiso 1 1 calc R . . H7B H 0.9718 0.1291 0.3632 0.061 Uiso 1 1 calc R . . Ni1 Ni 0.776709(19) 0.059925(18) 0.63503(4) 0.03769(12) Uani 1 1 d . . . N1 N 0.70760(15) 0.11627(15) 0.4271(3) 0.0454(5) Uani 1 1 d . . . C4 C 0.79762(17) 0.23575(17) 0.8309(4) 0.0458(5) Uani 1 1 d . . . H4A H 0.7876 0.2566 0.9470 0.055 Uiso 1 1 calc R . . H4B H 0.7814 0.2820 0.7521 0.055 Uiso 1 1 calc R . . O21 O 0.92320(19) -0.0852(2) 0.7285(4) 0.0722(8) Uani 1 1 d . . . C30 C 0.64458(19) -0.07768(17) 0.7179(5) 0.0509(6) Uani 1 1 d . . . C31 C 0.5754(3) -0.1069(2) 0.8384(7) 0.0768(13) Uani 1 1 d . . . H31C H 0.5694 -0.1690 0.8316 0.092 Uiso 1 1 calc R . . H31B H 0.5209 -0.0799 0.8080 0.092 Uiso 1 1 calc R . . H31A H 0.5910 -0.0906 0.9536 0.092 Uiso 1 1 calc R . . C5 C 0.89261(17) 0.21564(19) 0.8090(4) 0.0463(5) Uani 1 1 d . . . H5A H 0.9266 0.2638 0.8543 0.056 Uiso 1 1 calc R . . H5B H 0.9067 0.1644 0.8764 0.056 Uiso 1 1 calc R . . O30 O 0.67010(13) -0.00161(13) 0.7353(3) 0.0491(4) Uani 1 1 d . . . O10 O 0.80698(15) -0.05024(13) 0.4945(3) 0.0513(5) Uani 1 1 d . . . H10D H 0.760(3) -0.084(3) 0.521(6) 0.062 Uiso 1 1 d . . . C20 C 0.88986(17) -0.05164(17) 0.8550(4) 0.0468(5) Uani 1 1 d . . . C10 C 0.6247(2) 0.0717(2) 0.3983(5) 0.0555(6) Uani 1 1 d . . . H10B H 0.5902 0.0765 0.5026 0.067 Uiso 1 1 calc R . . H10A H 0.6369 0.0104 0.3807 0.067 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 C8 0.0619(16) 0.0678(18) 0.0371(13) 0.0064(12) 0.0080(11) 0.0035(13) C6 0.0445(10) 0.0462(11) 0.0455(12) 0.0048(11) 0.0027(10) -0.0028(9) C2 0.0470(11) 0.0431(12) 0.0631(18) 0.0024(12) -0.0023(12) 0.0089(9) C21 0.077(2) 0.0610(18) 0.063(2) 0.0137(16) -0.0069(18) 0.0144(16) C11 0.074(2) 0.072(2) 0.085(3) 0.004(2) -0.035(2) -0.0033(18) O31 0.0739(14) 0.0454(11) 0.100(2) -0.0157(13) 0.0126(16) -0.0144(11) C1 0.0563(14) 0.0488(13) 0.0473(14) 0.0038(11) -0.0019(11) 0.0033(11) O20 0.0529(9) 0.0428(8) 0.0426(9) 0.0056(7) 0.0015(8) 0.0087(7) C9 0.0687(18) 0.0643(17) 0.0376(13) -0.0019(11) -0.0038(12) 0.0060(14) N3 0.0416(9) 0.0419(9) 0.0387(10) 0.0038(8) 0.0051(8) 0.0023(7) C3 0.0445(11) 0.0429(11) 0.0545(15) 0.0011(11) 0.0077(11) 0.0031(9) N2 0.0433(9) 0.0367(9) 0.0381(9) -0.0013(7) 0.0025(8) 0.0012(7) C7 0.0552(13) 0.0559(14) 0.0411(13) 0.0020(11) 0.0093(11) 0.0032(11) Ni1 0.04100(17) 0.03550(16) 0.03656(17) 0.00008(11) 0.00169(11) 0.00174(10) N1 0.0487(11) 0.0452(10) 0.0422(10) 0.0016(9) -0.0059(9) 0.0020(8) C4 0.0505(12) 0.0418(11) 0.0450(13) -0.0033(9) 0.0012(9) -0.0016(9) O21 0.0710(15) 0.0852(18) 0.0603(14) -0.0064(13) 0.0000(12) 0.0370(14) C30 0.0481(12) 0.0365(11) 0.0680(18) 0.0053(11) 0.0005(12) -0.0021(9) C31 0.0652(19) 0.0487(15) 0.116(4) 0.011(2) 0.026(2) -0.0042(14) C5 0.0457(12) 0.0473(13) 0.0458(13) -0.0026(10) -0.0009(10) -0.0053(10) O30 0.0489(9) 0.0403(8) 0.0581(11) 0.0005(8) 0.0057(9) -0.0053(7) O10 0.0637(11) 0.0414(9) 0.0490(10) -0.0073(8) 0.0046(9) 0.0024(8) C20 0.0441(10) 0.0427(11) 0.0537(14) 0.0026(11) 0.0008(10) 0.0028(9) C10 0.0562(14) 0.0506(14) 0.0596(16) 0.0016(13) -0.0100(13) -0.0013(11) _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 C8 C7 1.520(4) . ? C8 C9 1.534(5) . ? C8 H8B 0.9900 . ? C8 H8A 0.9900 . ? C6 N3 1.494(4) . ? C6 C5 1.516(4) . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? C2 C3 1.523(4) . ? C2 C1 1.548(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C21 C20 1.503(5) . ? C21 H21C 0.9800 . ? C21 H21B 0.9800 . ? C21 H21A 0.9800 . ? C11 C10 1.539(5) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? O31 C30 1.260(4) . ? C1 N1 1.480(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? O20 C20 1.261(3) . ? O20 Ni1 2.1139(19) . ? C9 N1 1.496(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N3 C7 1.473(4) . ? N3 Ni1 2.097(2) . ? N3 H3C 0.9300 . ? C3 N2 1.482(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N2 C4 1.483(3) . ? N2 Ni1 2.115(2) . ? N2 H2C 0.9300 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? Ni1 O30 2.082(2) . ? Ni1 O10 2.109(2) . ? Ni1 N1 2.161(2) . ? N1 C10 1.488(4) . ? C4 C5 1.526(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? O21 C20 1.248(4) . ? C30 O30 1.265(3) . ? C30 C31 1.514(5) . ? C31 H31C 0.9800 . ? C31 H31B 0.9800 . ? C31 H31A 0.9800 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? O10 H10D 0.94(5) . ? C10 H10B 0.9900 . ? C10 H10A 0.9900 . ? 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 C7 C8 C9 116.4(3) . . ? C7 C8 H8B 108.2 . . ? C9 C8 H8B 108.2 . . ? C7 C8 H8A 108.2 . . ? C9 C8 H8A 108.2 . . ? H8B C8 H8A 107.3 . . ? N3 C6 C5 113.0(2) . . ? N3 C6 H6B 109.0 . . ? C5 C6 H6B 109.0 . . ? N3 C6 H6A 109.0 . . ? C5 C6 H6A 109.0 . . ? H6B C6 H6A 107.8 . . ? C3 C2 C1 116.6(2) . . ? C3 C2 H2A 108.2 . . ? C1 C2 H2A 108.2 . . ? C3 C2 H2B 108.2 . . ? C1 C2 H2B 108.2 . . ? H2A C2 H2B 107.3 . . ? C20 C21 H21C 109.5 . . ? C20 C21 H21B 109.5 . . ? H21C C21 H21B 109.5 . . ? C20 C21 H21A 109.5 . . ? H21C C21 H21A 109.5 . . ? H21B C21 H21A 109.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C1 C2 116.0(3) . . ? N1 C1 H1A 108.3 . . ? C2 C1 H1A 108.3 . . ? N1 C1 H1B 108.3 . . ? C2 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? C20 O20 Ni1 126.5(2) . . ? N1 C9 C8 117.0(3) . . ? N1 C9 H9A 108.1 . . ? C8 C9 H9A 108.1 . . ? N1 C9 H9B 108.1 . . ? C8 C9 H9B 108.1 . . ? H9A C9 H9B 107.3 . . ? C7 N3 C6 110.9(2) . . ? C7 N3 Ni1 113.68(18) . . ? C6 N3 Ni1 120.10(16) . . ? C7 N3 H3C 103.2 . . ? C6 N3 H3C 103.2 . . ? Ni1 N3 H3C 103.2 . . ? N2 C3 C2 113.3(2) . . ? N2 C3 H3A 108.9 . . ? C2 C3 H3A 108.9 . . ? N2 C3 H3B 108.9 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C3 N2 C4 112.0(2) . . ? C3 N2 Ni1 111.06(17) . . ? C4 N2 Ni1 123.33(16) . . ? C3 N2 H2C 102.4 . . ? C4 N2 H2C 102.4 . . ? Ni1 N2 H2C 102.4 . . ? N3 C7 C8 113.2(2) . . ? N3 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N3 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? O30 Ni1 N3 171.02(9) . . ? O30 Ni1 O10 90.11(9) . . ? N3 Ni1 O10 89.57(9) . . ? O30 Ni1 O20 83.73(8) . . ? N3 Ni1 O20 87.31(8) . . ? O10 Ni1 O20 91.55(8) . . ? O30 Ni1 N2 84.65(8) . . ? N3 Ni1 N2 94.93(9) . . ? O10 Ni1 N2 173.21(9) . . ? O20 Ni1 N2 83.60(8) . . ? O30 Ni1 N1 94.72(9) . . ? N3 Ni1 N1 94.26(9) . . ? O10 Ni1 N1 92.44(9) . . ? O20 Ni1 N1 175.72(9) . . ? N2 Ni1 N1 92.29(9) . . ? C1 N1 C10 111.5(2) . . ? C1 N1 C9 108.2(2) . . ? C10 N1 C9 107.5(3) . . ? C1 N1 Ni1 108.67(18) . . ? C10 N1 Ni1 111.08(18) . . ? C9 N1 Ni1 109.76(17) . . ? N2 C4 C5 112.5(2) . . ? N2 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? N2 C4 H4B 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? O31 C30 O30 125.5(3) . . ? O31 C30 C31 118.3(3) . . ? O30 C30 C31 116.1(3) . . ? C30 C31 H31C 109.5 . . ? C30 C31 H31B 109.5 . . ? H31C C31 H31B 109.5 . . ? C30 C31 H31A 109.5 . . ? H31C C31 H31A 109.5 . . ? H31B C31 H31A 109.5 . . ? C6 C5 C4 114.0(2) . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5B 108.8 . . ? C4 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C30 O30 Ni1 130.3(2) . . ? Ni1 O10 H10D 100(3) . . ? O21 C20 O20 124.6(3) . . ? O21 C20 C21 118.3(3) . . ? O20 C20 C21 117.0(3) . . ? N1 C10 C11 117.1(3) . . ? N1 C10 H10B 108.0 . . ? C11 C10 H10B 108.0 . . ? N1 C10 H10A 108.0 . . ? C11 C10 H10A 108.0 . . ? H10B C10 H10A 107.3 . . ? 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 C3 C2 C1 N1 51.2(4) . . . . ? C7 C8 C9 N1 67.5(4) . . . . ? C5 C6 N3 C7 174.9(2) . . . . ? C5 C6 N3 Ni1 39.0(3) . . . . ? C1 C2 C3 N2 27.1(4) . . . . ? C2 C3 N2 C4 71.9(3) . . . . ? C2 C3 N2 Ni1 -70.4(2) . . . . ? C6 N3 C7 C8 -78.2(3) . . . . ? Ni1 N3 C7 C8 60.7(3) . . . . ? C9 C8 C7 N3 -67.0(4) . . . . ? C7 N3 Ni1 O30 133.7(5) . . . . ? C6 N3 Ni1 O30 -91.5(6) . . . . ? C7 N3 Ni1 O10 45.73(19) . . . . ? C6 N3 Ni1 O10 -179.5(2) . . . . ? C7 N3 Ni1 O20 137.31(19) . . . . ? C6 N3 Ni1 O20 -87.9(2) . . . . ? C7 N3 Ni1 N2 -139.36(18) . . . . ? C6 N3 Ni1 N2 -4.6(2) . . . . ? C7 N3 Ni1 N1 -46.7(2) . . . . ? C6 N3 Ni1 N1 88.1(2) . . . . ? C20 O20 Ni1 O30 104.2(2) . . . . ? C20 O20 Ni1 N3 -75.2(2) . . . . ? C20 O20 Ni1 O10 14.3(2) . . . . ? C20 O20 Ni1 N2 -170.5(2) . . . . ? C20 O20 Ni1 N1 173.1(11) . . . . ? C3 N2 Ni1 O30 -52.22(18) . . . . ? C4 N2 Ni1 O30 170.5(2) . . . . ? C3 N2 Ni1 N3 136.78(17) . . . . ? C4 N2 Ni1 N3 -0.5(2) . . . . ? C3 N2 Ni1 O10 -91.9(8) . . . . ? C4 N2 Ni1 O10 130.9(7) . . . . ? C3 N2 Ni1 O20 -136.48(17) . . . . ? C4 N2 Ni1 O20 86.2(2) . . . . ? C3 N2 Ni1 N1 42.31(18) . . . . ? C4 N2 Ni1 N1 -95.0(2) . . . . ? C2 C1 N1 C10 55.1(3) . . . . ? C2 C1 N1 C9 173.2(2) . . . . ? C2 C1 N1 Ni1 -67.7(3) . . . . ? C8 C9 N1 C1 61.5(3) . . . . ? C8 C9 N1 C10 -177.9(3) . . . . ? C8 C9 N1 Ni1 -57.0(3) . . . . ? O30 Ni1 N1 C1 104.92(19) . . . . ? N3 Ni1 N1 C1 -75.02(19) . . . . ? O10 Ni1 N1 C1 -164.77(19) . . . . ? O20 Ni1 N1 C1 36.4(13) . . . . ? N2 Ni1 N1 C1 20.10(19) . . . . ? O30 Ni1 N1 C10 -18.1(2) . . . . ? N3 Ni1 N1 C10 161.9(2) . . . . ? O10 Ni1 N1 C10 72.2(2) . . . . ? O20 Ni1 N1 C10 -86.7(12) . . . . ? N2 Ni1 N1 C10 -103.0(2) . . . . ? O30 Ni1 N1 C9 -136.9(2) . . . . ? N3 Ni1 N1 C9 43.1(2) . . . . ? O10 Ni1 N1 C9 -46.6(2) . . . . ? O20 Ni1 N1 C9 154.5(11) . . . . ? N2 Ni1 N1 C9 138.3(2) . . . . ? C3 N2 C4 C5 -165.1(2) . . . . ? Ni1 N2 C4 C5 -28.2(3) . . . . ? N3 C6 C5 C4 -77.6(3) . . . . ? N2 C4 C5 C6 70.3(3) . . . . ? O31 C30 O30 Ni1 -16.0(5) . . . . ? C31 C30 O30 Ni1 167.0(3) . . . . ? N3 Ni1 O30 C30 -83.5(6) . . . . ? O10 Ni1 O30 C30 4.4(3) . . . . ? O20 Ni1 O30 C30 -87.1(3) . . . . ? N2 Ni1 O30 C30 -171.2(3) . . . . ? N1 Ni1 O30 C30 96.9(3) . . . . ? Ni1 O20 C20 O21 13.4(4) . . . . ? Ni1 O20 C20 C21 -167.4(2) . . . . ? C1 N1 C10 C11 60.5(4) . . . . ? C9 N1 C10 C11 -58.0(4) . . . . ? Ni1 N1 C10 C11 -178.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.261 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.129 # Attachment 'web_deposit_cif_file_6_BernhardSpingler_1312475891.4.cif' data_am200406 _database_code_depnum_ccdc_archive 'CCDC 661096' #TrackingRef 'web_deposit_cif_file_6_BernhardSpingler_1312475891.4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H33 Cl2 Cu N3 O4' _chemical_formula_weight 465.89 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 11.898(5) _cell_length_b 14.067(5) _cell_length_c 13.146(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.368(5) _cell_angle_gamma 90.000(5) _cell_volume 2200.2(15) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 980 _exptl_absorpt_coefficient_mu 1.260 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8466 _exptl_absorpt_correction_T_max 0.9045 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '/f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 13 _diffrn_standards_decay_% ? _diffrn_reflns_number 33708 _diffrn_reflns_av_R_equivalents 0.1201 _diffrn_reflns_av_sigmaI/netI 0.0667 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 29.13 _reflns_number_total 5844 _reflns_number_gt 3903 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _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^)+(0.0985P)^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 5844 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0897 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1472 _refine_ls_wR_factor_gt 0.1358 _refine_ls_goodness_of_fit_ref 0.923 _refine_ls_restrained_S_all 0.923 _refine_ls_shift/su_max 0.010 _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 Cl41 Cl 0.7159(2) 0.64523(12) 0.44216(14) 0.1187(6) Uani 1 1 d . . . O20 O 0.86479(17) 0.41333(15) 0.16457(15) 0.0395(4) Uani 1 1 d . . . N3 N 0.6265(2) 0.25360(17) 0.04423(19) 0.0375(5) Uani 1 1 d . . . H3C H 0.5620 0.2729 0.0780 0.045 Uiso 1 1 calc R . . N1 N 0.74662(19) 0.44650(17) -0.05494(18) 0.0339(5) Uani 1 1 d . . . O30 O 0.63466(19) 0.42531(16) 0.16687(18) 0.0466(5) Uani 1 1 d . . . O21 O 0.8246(2) 0.31794(17) 0.29472(18) 0.0487(5) Uani 1 1 d . . . C1 C 0.8652(2) 0.4687(2) -0.0803(2) 0.0379(6) Uani 1 1 d . . . H1A H 0.8979 0.5051 -0.0229 0.046 Uiso 1 1 calc R . . H1B H 0.8648 0.5111 -0.1404 0.046 Uiso 1 1 calc R . . Cl40 Cl 0.84438(13) 0.74007(14) 0.28321(16) 0.1105(6) Uani 1 1 d . . . N2 N 0.8567(2) 0.26573(17) 0.00902(19) 0.0353(5) Uani 1 1 d . . . H2C H 0.8233 0.2476 -0.0521 0.042 Uiso 1 1 calc R . . C2 C 0.9435(2) 0.3853(2) -0.1028(2) 0.0388(6) Uani 1 1 d . . . H2B H 0.9128 0.3501 -0.1620 0.047 Uiso 1 1 calc R . . H2A H 1.0175 0.4112 -0.1230 0.047 Uiso 1 1 calc R . . C30 C 0.5516(2) 0.3968(2) 0.2182(2) 0.0393(6) Uani 1 1 d . . . C4 C 0.8685(3) 0.1787(2) 0.0722(2) 0.0424(6) Uani 1 1 d . . . H4A H 0.8758 0.1963 0.1448 0.051 Uiso 1 1 calc R . . H4B H 0.9368 0.1433 0.0522 0.051 Uiso 1 1 calc R . . C9 C 0.6910(2) 0.3956(2) -0.1398(2) 0.0368(6) Uani 1 1 d . . . H9A H 0.7437 0.3473 -0.1663 0.044 Uiso 1 1 calc R . . H9B H 0.6761 0.4417 -0.1953 0.044 Uiso 1 1 calc R . . C7 C 0.5923(2) 0.2491(2) -0.0639(2) 0.0385(6) Uani 1 1 d . . . H7A H 0.5196 0.2152 -0.0693 0.046 Uiso 1 1 calc R . . H7B H 0.6488 0.2118 -0.1019 0.046 Uiso 1 1 calc R . . O31 O 0.4987(2) 0.32150(18) 0.20559(19) 0.0491(5) Uani 1 1 d . . . C31 C 0.5169(3) 0.4634(3) 0.3030(3) 0.0502(8) Uani 1 1 d . . . H31A H 0.5099 0.5281 0.2762 0.060 Uiso 1 1 calc R . . H31B H 0.5739 0.4622 0.3571 0.060 Uiso 1 1 calc R . . H31C H 0.4445 0.4429 0.3305 0.060 Uiso 1 1 calc R . . C11 C 0.7317(3) 0.6010(2) 0.0437(3) 0.0465(7) Uani 1 1 d . . . H11A H 0.7994 0.6330 0.0190 0.056 Uiso 1 1 calc R . . H11B H 0.7506 0.5624 0.1034 0.056 Uiso 1 1 calc R . . H11C H 0.6754 0.6487 0.0622 0.056 Uiso 1 1 calc R . . C10 C 0.6849(3) 0.5378(2) -0.0389(3) 0.0435(7) Uani 1 1 d . . . H10A H 0.6058 0.5228 -0.0225 0.052 Uiso 1 1 calc R . . H10B H 0.6848 0.5738 -0.1036 0.052 Uiso 1 1 calc R . . C3 C 0.9622(2) 0.3150(2) -0.0163(2) 0.0384(6) Uani 1 1 d . . . H3A H 1.0195 0.2677 -0.0365 0.046 Uiso 1 1 calc R . . H3B H 0.9907 0.3492 0.0444 0.046 Uiso 1 1 calc R . . C8 C 0.5804(2) 0.3462(2) -0.1130(2) 0.0400(6) Uani 1 1 d . . . H8A H 0.5379 0.3879 -0.0663 0.048 Uiso 1 1 calc R . . H8B H 0.5351 0.3393 -0.1760 0.048 Uiso 1 1 calc R . . C5 C 0.7652(3) 0.1165(2) 0.0567(3) 0.0479(7) Uani 1 1 d . . . H5B H 0.7765 0.0566 0.0949 0.057 Uiso 1 1 calc R . . H5A H 0.7597 0.0998 -0.0164 0.057 Uiso 1 1 calc R . . C20 C 0.8738(3) 0.3874(2) 0.2572(2) 0.0388(6) Uani 1 1 d . . . C40 C 0.7194(4) 0.6822(5) 0.3142(5) 0.0860(15) Uani 1 1 d . . . H40A H 0.7101 0.6260 0.2696 0.103 Uiso 1 1 calc R . . H40B H 0.6554 0.7256 0.3010 0.103 Uiso 1 1 calc R . . C21 C 0.9512(3) 0.4465(3) 0.3222(3) 0.0542(8) Uani 1 1 d . . . H21A H 0.9066 0.4885 0.3656 0.065 Uiso 1 1 calc R . . H21B H 0.9998 0.4848 0.2784 0.065 Uiso 1 1 calc R . . H21C H 0.9975 0.4047 0.3648 0.065 Uiso 1 1 calc R . . C6 C 0.6539(3) 0.1600(2) 0.0892(3) 0.0461(7) Uani 1 1 d . . . H6B H 0.5929 0.1151 0.0714 0.055 Uiso 1 1 calc R . . H6A H 0.6548 0.1667 0.1642 0.055 Uiso 1 1 calc R . . Cu1 Cu 0.74383(3) 0.35111(2) 0.08364(3) 0.03452(12) 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 Cl41 0.1777(19) 0.0941(11) 0.0842(10) -0.0180(8) -0.0029(11) -0.0032(11) O20 0.0429(10) 0.0466(11) 0.0291(10) 0.0002(8) -0.0011(8) -0.0080(8) N3 0.0396(12) 0.0410(12) 0.0319(12) -0.0043(9) 0.0041(10) -0.0090(9) N1 0.0347(11) 0.0349(11) 0.0320(11) 0.0005(9) 0.0002(9) -0.0011(9) O30 0.0458(11) 0.0469(12) 0.0473(13) -0.0066(10) 0.0126(10) -0.0012(9) O21 0.0608(13) 0.0484(12) 0.0368(11) 0.0043(9) 0.0008(10) -0.0100(10) C1 0.0366(13) 0.0401(14) 0.0371(14) 0.0025(11) 0.0036(11) -0.0024(11) Cl40 0.0769(8) 0.1319(14) 0.1229(14) -0.0327(11) 0.0091(8) -0.0085(8) N2 0.0373(11) 0.0373(11) 0.0314(11) -0.0010(9) 0.0011(9) 0.0016(9) C2 0.0340(12) 0.0475(15) 0.0350(14) 0.0002(12) 0.0051(11) -0.0021(11) C30 0.0405(14) 0.0465(16) 0.0309(13) 0.0019(12) 0.0023(11) 0.0104(12) C4 0.0513(16) 0.0401(14) 0.0356(15) 0.0020(11) -0.0009(13) 0.0053(12) C9 0.0388(13) 0.0416(14) 0.0300(13) 0.0014(11) -0.0002(11) 0.0001(11) C7 0.0376(13) 0.0439(15) 0.0339(14) -0.0052(11) 0.0019(11) -0.0069(11) O31 0.0480(12) 0.0540(13) 0.0455(13) -0.0045(10) 0.0106(10) -0.0053(10) C31 0.062(2) 0.0484(17) 0.0402(16) 0.0002(13) 0.0074(15) 0.0121(15) C11 0.0445(15) 0.0388(15) 0.0561(19) -0.0054(13) 0.0024(14) 0.0005(12) C10 0.0393(14) 0.0415(15) 0.0496(17) -0.0016(13) 0.0005(13) 0.0014(12) C3 0.0316(12) 0.0462(15) 0.0373(14) -0.0007(12) 0.0018(11) 0.0009(11) C8 0.0367(13) 0.0454(15) 0.0380(14) -0.0046(12) -0.0025(11) -0.0006(12) C5 0.0617(19) 0.0417(15) 0.0403(16) 0.0056(13) 0.0000(15) -0.0022(14) C20 0.0428(14) 0.0427(14) 0.0310(13) 0.0004(11) 0.0011(12) -0.0017(12) C40 0.075(3) 0.096(4) 0.087(4) -0.020(3) 0.000(3) 0.013(3) C21 0.060(2) 0.065(2) 0.0380(16) 0.0005(15) -0.0042(15) -0.0168(17) C6 0.0561(17) 0.0441(16) 0.0381(15) 0.0033(12) 0.0042(14) -0.0101(13) Cu1 0.03657(17) 0.03754(18) 0.02948(17) -0.00162(14) 0.00240(12) -0.00297(14) _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 Cl41 C40 1.762(7) . ? O20 C20 1.276(4) . ? O20 Cu1 1.987(2) . ? N3 C7 1.478(4) . ? N3 C6 1.479(4) . ? N3 Cu1 2.022(2) . ? N3 H3C 0.9300 . ? N1 C9 1.478(4) . ? N1 C1 1.485(3) . ? N1 C10 1.495(4) . ? N1 Cu1 2.263(2) . ? O30 C30 1.266(4) . ? O30 Cu1 1.998(2) . ? O21 C20 1.242(4) . ? C1 C2 1.528(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? Cl40 C40 1.746(6) . ? N2 C3 1.474(4) . ? N2 C4 1.486(4) . ? N2 Cu1 2.056(2) . ? N2 H2C 0.9300 . ? C2 C3 1.523(4) . ? C2 H2B 0.9900 . ? C2 H2A 0.9900 . ? C30 O31 1.242(4) . ? C30 C31 1.516(4) . ? C4 C5 1.521(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C9 C8 1.531(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C7 C8 1.517(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C11 C10 1.506(5) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C5 C6 1.523(5) . ? C5 H5B 0.9900 . ? C5 H5A 0.9900 . ? C20 C21 1.503(5) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? 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 C20 O20 Cu1 116.18(19) . . ? C7 N3 C6 113.9(2) . . ? C7 N3 Cu1 117.45(17) . . ? C6 N3 Cu1 110.6(2) . . ? C7 N3 H3C 104.4 . . ? C6 N3 H3C 104.4 . . ? Cu1 N3 H3C 104.4 . . ? C9 N1 C1 110.7(2) . . ? C9 N1 C10 107.7(2) . . ? C1 N1 C10 108.6(2) . . ? C9 N1 Cu1 108.16(17) . . ? C1 N1 Cu1 108.94(18) . . ? C10 N1 Cu1 112.72(18) . . ? C30 O30 Cu1 129.7(2) . . ? N1 C1 C2 117.6(2) . . ? N1 C1 H1A 107.9 . . ? C2 C1 H1A 107.9 . . ? N1 C1 H1B 107.9 . . ? C2 C1 H1B 107.9 . . ? H1A C1 H1B 107.2 . . ? C3 N2 C4 115.9(2) . . ? C3 N2 Cu1 113.16(18) . . ? C4 N2 Cu1 105.91(17) . . ? C3 N2 H2C 107.1 . . ? C4 N2 H2C 107.1 . . ? Cu1 N2 H2C 107.1 . . ? C3 C2 C1 116.1(2) . . ? C3 C2 H2B 108.3 . . ? C1 C2 H2B 108.3 . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2A 108.3 . . ? H2B C2 H2A 107.4 . . ? O31 C30 O30 126.6(3) . . ? O31 C30 C31 119.0(3) . . ? O30 C30 C31 114.4(3) . . ? N2 C4 C5 109.1(3) . . ? N2 C4 H4A 109.9 . . ? C5 C4 H4A 109.9 . . ? N2 C4 H4B 109.9 . . ? C5 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? N1 C9 C8 115.3(2) . . ? N1 C9 H9A 108.4 . . ? C8 C9 H9A 108.4 . . ? N1 C9 H9B 108.4 . . ? C8 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? N3 C7 C8 113.3(2) . . ? N3 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N3 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C10 C11 115.4(3) . . ? N1 C10 H10A 108.4 . . ? C11 C10 H10A 108.4 . . ? N1 C10 H10B 108.4 . . ? C11 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? N2 C3 C2 110.7(2) . . ? N2 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C7 C8 C9 115.4(2) . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8A 108.4 . . ? C7 C8 H8B 108.4 . . ? C9 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C4 C5 C6 115.7(3) . . ? C4 C5 H5B 108.4 . . ? C6 C5 H5B 108.3 . . ? C4 C5 H5A 108.4 . . ? C6 C5 H5A 108.4 . . ? H5B C5 H5A 107.4 . . ? O21 C20 O20 124.6(3) . . ? O21 C20 C21 119.9(3) . . ? O20 C20 C21 115.5(3) . . ? Cl40 C40 Cl41 112.7(3) . . ? Cl40 C40 H40A 109.1 . . ? Cl41 C40 H40A 109.1 . . ? Cl40 C40 H40B 109.1 . . ? Cl41 C40 H40B 109.1 . . ? H40A C40 H40B 107.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C6 C5 115.8(2) . . ? N3 C6 H6B 108.3 . . ? C5 C6 H6B 108.3 . . ? N3 C6 H6A 108.3 . . ? C5 C6 H6A 108.3 . . ? H6B C6 H6A 107.4 . . ? O20 Cu1 O30 87.01(10) . . ? O20 Cu1 N3 158.78(10) . . ? O30 Cu1 N3 92.56(10) . . ? O20 Cu1 N2 92.27(10) . . ? O30 Cu1 N2 174.63(10) . . ? N3 Cu1 N2 86.19(10) . . ? O20 Cu1 N1 98.94(9) . . ? O30 Cu1 N1 98.28(9) . . ? N3 Cu1 N1 102.10(10) . . ? N2 Cu1 N1 87.09(9) . . ? 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 C9 N1 C1 C2 -60.3(3) . . . . ? C10 N1 C1 C2 -178.4(3) . . . . ? Cu1 N1 C1 C2 58.5(3) . . . . ? N1 C1 C2 C3 -61.9(4) . . . . ? Cu1 O30 C30 O31 -23.0(5) . . . . ? Cu1 O30 C30 C31 156.6(2) . . . . ? C3 N2 C4 C5 -157.6(3) . . . . ? Cu1 N2 C4 C5 76.0(3) . . . . ? C1 N1 C9 C8 164.5(2) . . . . ? C10 N1 C9 C8 -76.9(3) . . . . ? Cu1 N1 C9 C8 45.2(3) . . . . ? C6 N3 C7 C8 -171.9(2) . . . . ? Cu1 N3 C7 C8 -40.3(3) . . . . ? C9 N1 C10 C11 -178.6(3) . . . . ? C1 N1 C10 C11 -58.6(3) . . . . ? Cu1 N1 C10 C11 62.2(3) . . . . ? C4 N2 C3 C2 164.6(2) . . . . ? Cu1 N2 C3 C2 -72.8(3) . . . . ? C1 C2 C3 N2 64.6(3) . . . . ? N3 C7 C8 C9 76.1(3) . . . . ? N1 C9 C8 C7 -82.4(3) . . . . ? N2 C4 C5 C6 -62.4(3) . . . . ? Cu1 O20 C20 O21 11.0(4) . . . . ? Cu1 O20 C20 C21 -169.7(2) . . . . ? C7 N3 C6 C5 73.8(3) . . . . ? Cu1 N3 C6 C5 -61.0(3) . . . . ? C4 C5 C6 N3 54.4(4) . . . . ? C20 O20 Cu1 O30 70.5(2) . . . . ? C20 O20 Cu1 N3 -18.9(4) . . . . ? C20 O20 Cu1 N2 -104.2(2) . . . . ? C20 O20 Cu1 N1 168.4(2) . . . . ? C30 O30 Cu1 O20 -126.1(3) . . . . ? C30 O30 Cu1 N3 32.6(3) . . . . ? C30 O30 Cu1 N2 -43.8(12) . . . . ? C30 O30 Cu1 N1 135.3(3) . . . . ? C7 N3 Cu1 O20 -158.2(2) . . . . ? C6 N3 Cu1 O20 -25.2(4) . . . . ? C7 N3 Cu1 O30 113.4(2) . . . . ? C6 N3 Cu1 O30 -113.49(19) . . . . ? C7 N3 Cu1 N2 -71.8(2) . . . . ? C6 N3 Cu1 N2 61.28(19) . . . . ? C7 N3 Cu1 N1 14.4(2) . . . . ? C6 N3 Cu1 N1 147.48(18) . . . . ? C3 N2 Cu1 O20 -38.7(2) . . . . ? C4 N2 Cu1 O20 89.29(19) . . . . ? C3 N2 Cu1 O30 -120.8(10) . . . . ? C4 N2 Cu1 O30 7.2(12) . . . . ? C3 N2 Cu1 N3 162.5(2) . . . . ? C4 N2 Cu1 N3 -69.5(2) . . . . ? C3 N2 Cu1 N1 60.1(2) . . . . ? C4 N2 Cu1 N1 -171.9(2) . . . . ? C9 N1 Cu1 O20 161.09(17) . . . . ? C1 N1 Cu1 O20 40.70(19) . . . . ? C10 N1 Cu1 O20 -79.92(19) . . . . ? C9 N1 Cu1 O30 -110.66(17) . . . . ? C1 N1 Cu1 O30 128.95(18) . . . . ? C10 N1 Cu1 O30 8.3(2) . . . . ? C9 N1 Cu1 N3 -16.22(18) . . . . ? C1 N1 Cu1 N3 -136.61(18) . . . . ? C10 N1 Cu1 N3 102.8(2) . . . . ? C9 N1 Cu1 N2 69.25(18) . . . . ? C1 N1 Cu1 N2 -51.14(18) . . . . ? C10 N1 Cu1 N2 -171.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.728 _refine_diff_density_min -0.684 _refine_diff_density_rms 0.087 # Attachment 'web_deposit_cif_file_10_BernhardSpingler_1312475891.L1.cif' data_am050406 _database_code_depnum_ccdc_archive 'CCDC 661097' #TrackingRef 'web_deposit_cif_file_10_BernhardSpingler_1312475891.L1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H28 F9 N3 O9 S3' _chemical_formula_weight 649.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 8.6228(2) _cell_length_b 20.3707(4) _cell_length_c 15.0841(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2649.6(1) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 26788 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.628 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 3.612 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4318 _exptl_absorpt_correction_T_max 0.6389 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 1.54186 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS 2T' _diffrn_measurement_method '/o oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 3 _diffrn_standards_decay_% ? _diffrn_reflns_number 25107 _diffrn_reflns_av_R_equivalents 0.0902 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 66.46 _reflns_number_total 4361 _reflns_number_gt 3802 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe, 2005)' _computing_cell_refinement 'X-Area (Stoe, 2005)' _computing_data_reduction 'X-RED32 (Stoe, 2005)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _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^)+(0.0639P)^2^+4.0568P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(3) _refine_ls_number_reflns 4361 _refine_ls_number_parameters 344 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1468 _refine_ls_wR_factor_gt 0.1376 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _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 C1 C 0.9088(6) 0.0632(3) 0.3135(3) 0.0344(12) Uani 1 1 d . . . H1B H 0.9008 0.0942 0.3639 0.041 Uiso 1 1 calc R . . H1A H 1.0199 0.0591 0.2980 0.041 Uiso 1 1 calc R . . C2 C 0.8499(7) -0.0033(3) 0.3433(4) 0.0376(12) Uani 1 1 d . . . H2A H 0.7370 -0.0055 0.3318 0.045 Uiso 1 1 calc R . . H2B H 0.9001 -0.0375 0.3065 0.045 Uiso 1 1 calc R . . C3 C 0.8777(6) -0.0194(3) 0.4390(4) 0.0384(13) Uani 1 1 d . . . H3B H 0.9892 -0.0128 0.4520 0.046 Uiso 1 1 calc R . . H3A H 0.8545 -0.0665 0.4484 0.046 Uiso 1 1 calc R . . C4 C 0.6115(6) 0.0154(3) 0.4937(5) 0.0477(15) Uani 1 1 d . . . H4A H 0.5761 -0.0274 0.5172 0.057 Uiso 1 1 calc R . . H4B H 0.5869 0.0165 0.4296 0.057 Uiso 1 1 calc R . . C5 C 0.5233(6) 0.0695(3) 0.5397(4) 0.0460(14) Uani 1 1 d . . . H5B H 0.4123 0.0572 0.5408 0.055 Uiso 1 1 calc R . . H5A H 0.5593 0.0716 0.6019 0.055 Uiso 1 1 calc R . . C6 C 0.5363(6) 0.1369(3) 0.5005(3) 0.0349(12) Uani 1 1 d . . . H6B H 0.6470 0.1470 0.4897 0.042 Uiso 1 1 calc R . . H6A H 0.4964 0.1694 0.5437 0.042 Uiso 1 1 calc R . . C7 C 0.5126(6) 0.1951(3) 0.3529(3) 0.0322(11) Uani 1 1 d . . . H7A H 0.5166 0.2377 0.3844 0.039 Uiso 1 1 calc R . . H7B H 0.4404 0.2001 0.3023 0.039 Uiso 1 1 calc R . . C8 C 0.6720(6) 0.1799(3) 0.3172(4) 0.0314(11) Uani 1 1 d . . . H8A H 0.7444 0.1730 0.3673 0.038 Uiso 1 1 calc R . . H8B H 0.7100 0.2177 0.2822 0.038 Uiso 1 1 calc R . . C9 C 0.6694(6) 0.1184(3) 0.2586(3) 0.0317(12) Uani 1 1 d . . . H9B H 0.6094 0.0838 0.2894 0.038 Uiso 1 1 calc R . . H9A H 0.6141 0.1290 0.2029 0.038 Uiso 1 1 calc R . . C10 C 0.8154(5) 0.0433(3) 0.1605(3) 0.0313(11) Uani 1 1 d . . . H10B H 0.9184 0.0227 0.1523 0.038 Uiso 1 1 calc R . . H10A H 0.7409 0.0082 0.1761 0.038 Uiso 1 1 calc R . . C11 C 0.7659(7) 0.0745(3) 0.0748(4) 0.0407(13) Uani 1 1 d . . . H11C H 0.7690 0.0417 0.0272 0.049 Uiso 1 1 calc R . . H11B H 0.8363 0.1107 0.0603 0.049 Uiso 1 1 calc R . . H11A H 0.6600 0.0914 0.0808 0.049 Uiso 1 1 calc R . . C20 C 0.3228(7) -0.1044(3) 0.3294(4) 0.0429(14) Uani 1 1 d . . . C30 C -0.0937(6) -0.1788(3) 0.1466(4) 0.0426(14) Uani 1 1 d . . . C40 C 1.1855(10) 0.2109(4) 0.0487(7) 0.073(3) Uani 1 1 d . . . N1 N 0.8243(5) 0.0917(2) 0.2359(3) 0.0319(10) Uani 1 1 d . . . H1D H 0.8835 0.1269 0.2159 0.038 Uiso 1 1 calc R . . N2 N 0.7840(5) 0.0203(2) 0.5051(3) 0.0357(10) Uani 1 1 d . . . H2D H 0.8091 0.0066 0.5614 0.043 Uiso 1 1 calc R . . H2E H 0.8124 0.0637 0.5003 0.043 Uiso 1 1 calc R . . N3 N 0.4483(5) 0.1441(2) 0.4150(3) 0.0338(10) Uani 1 1 d . . . H3D H 0.3471 0.1547 0.4280 0.041 Uiso 1 1 calc R . . H3E H 0.4478 0.1042 0.3864 0.041 Uiso 1 1 calc R . . O20 O 0.2148(4) -0.0258(2) 0.2135(2) 0.0399(9) Uani 1 1 d . . . O21 O 0.4870(4) -0.0206(2) 0.2464(3) 0.0527(12) Uani 1 1 d . . . O22 O 0.3038(5) 0.0206(2) 0.3519(3) 0.0483(10) Uani 1 1 d . . . O30 O -0.1257(4) -0.08208(17) 0.0403(3) 0.0437(9) Uani 1 1 d . . . O31 O 0.0871(4) -0.1552(2) 0.0150(3) 0.0445(10) Uani 1 1 d . . . O32 O -0.1711(4) -0.19168(18) -0.0161(2) 0.0375(9) Uani 1 1 d . . . O40 O 1.3403(7) 0.1645(5) 0.1751(5) 0.129(3) Uani 1 1 d . . . O41 O 1.1531(6) 0.0950(2) 0.1047(3) 0.0573(12) Uani 1 1 d . . . O42 O 1.0700(6) 0.1810(2) 0.1994(3) 0.0654(15) Uani 1 1 d . . . F20 F 0.4289(5) -0.1112(2) 0.3930(3) 0.0673(11) Uani 1 1 d . . . F21 F 0.1830(5) -0.1145(2) 0.3662(3) 0.0677(11) Uani 1 1 d . . . F22 F 0.3450(6) -0.15064(18) 0.2699(3) 0.0698(12) Uani 1 1 d . . . F30 F -0.0116(5) -0.1447(2) 0.2027(3) 0.0731(13) Uani 1 1 d . . . F31 F -0.2388(5) -0.1757(3) 0.1729(3) 0.0851(15) Uani 1 1 d . . . F32 F -0.0485(6) -0.2414(2) 0.1530(3) 0.0792(14) Uani 1 1 d . . . F40 F 1.0487(7) 0.2063(3) 0.0069(5) 0.133(3) Uani 1 1 d . . . F41 F 1.2896(6) 0.1958(2) -0.0107(3) 0.0923(16) Uani 1 1 d . . . F42 F 1.2094(10) 0.2717(2) 0.0733(6) 0.165(4) Uani 1 1 d . . . S20 S 0.33237(14) -0.02357(6) 0.27976(9) 0.0308(3) Uani 1 1 d . . . S30 S -0.07381(13) -0.14899(6) 0.03513(8) 0.0287(3) Uani 1 1 d . . . S40 S 1.19168(16) 0.15636(8) 0.14331(10) 0.0432(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 C1 0.036(3) 0.037(3) 0.030(3) 0.002(2) -0.007(2) 0.001(2) C2 0.045(3) 0.031(3) 0.037(3) 0.003(2) -0.006(2) 0.002(2) C3 0.037(3) 0.037(3) 0.042(3) 0.007(2) -0.004(2) 0.007(2) C4 0.025(3) 0.049(4) 0.069(4) 0.007(3) -0.010(3) -0.009(2) C5 0.027(3) 0.073(4) 0.038(3) 0.013(3) 0.002(2) -0.002(3) C6 0.033(3) 0.046(3) 0.026(2) -0.011(2) -0.003(2) -0.004(2) C7 0.032(2) 0.033(3) 0.032(3) -0.007(2) -0.005(2) 0.004(2) C8 0.035(3) 0.024(3) 0.036(3) -0.002(2) 0.006(2) -0.004(2) C9 0.028(2) 0.036(3) 0.032(3) -0.003(2) 0.002(2) 0.004(2) C10 0.028(2) 0.042(3) 0.023(3) -0.002(2) 0.0002(19) -0.001(2) C11 0.041(3) 0.052(4) 0.029(3) -0.004(3) 0.002(2) -0.003(3) C20 0.059(4) 0.035(3) 0.035(3) -0.012(3) -0.012(3) 0.008(3) C30 0.042(3) 0.044(4) 0.042(3) -0.011(3) 0.001(3) -0.006(2) C40 0.073(5) 0.038(4) 0.108(7) 0.005(4) 0.039(5) -0.013(3) N1 0.033(2) 0.034(3) 0.029(2) -0.0037(19) -0.0029(17) 0.0075(18) N2 0.031(2) 0.042(3) 0.035(2) 0.010(2) 0.0000(18) 0.0004(18) N3 0.030(2) 0.033(3) 0.038(3) -0.009(2) -0.0047(19) 0.0021(18) O20 0.0348(19) 0.047(2) 0.038(2) 0.0003(17) -0.0169(16) -0.0044(16) O21 0.0287(19) 0.074(3) 0.056(3) -0.013(2) 0.0078(18) -0.015(2) O22 0.063(3) 0.043(3) 0.039(2) -0.0157(18) 0.0011(19) 0.007(2) O30 0.049(2) 0.022(2) 0.061(2) -0.0040(18) 0.000(2) 0.0112(16) O31 0.0169(17) 0.062(3) 0.055(3) -0.0017(19) 0.0060(16) 0.0013(16) O32 0.0298(19) 0.042(2) 0.041(2) -0.0120(18) -0.0096(15) -0.0054(15) O40 0.054(3) 0.244(10) 0.089(5) -0.015(5) -0.033(3) -0.032(5) O41 0.091(4) 0.030(2) 0.050(3) -0.0105(19) -0.001(2) -0.001(2) O42 0.078(3) 0.040(3) 0.077(3) -0.023(2) 0.044(3) -0.020(2) F20 0.087(3) 0.060(3) 0.055(2) 0.0052(19) -0.030(2) 0.017(2) F21 0.077(3) 0.073(3) 0.053(2) 0.009(2) 0.004(2) -0.027(2) F22 0.111(3) 0.033(2) 0.066(3) -0.0125(19) -0.008(2) 0.011(2) F30 0.097(3) 0.083(3) 0.039(2) -0.009(2) -0.019(2) -0.023(3) F31 0.058(2) 0.142(4) 0.055(3) 0.001(3) 0.028(2) -0.014(3) F32 0.137(4) 0.053(3) 0.048(2) 0.0158(19) -0.003(2) 0.015(2) F40 0.086(4) 0.156(6) 0.158(6) 0.102(5) -0.010(4) 0.018(4) F41 0.105(4) 0.094(4) 0.078(3) 0.000(3) 0.038(3) -0.026(3) F42 0.238(8) 0.032(3) 0.223(8) -0.009(4) 0.144(7) -0.032(4) S20 0.0313(6) 0.0312(7) 0.0299(6) -0.0043(5) -0.0033(5) -0.0034(5) S30 0.0242(5) 0.0316(7) 0.0302(6) -0.0014(5) -0.0002(5) -0.0001(4) S40 0.0382(7) 0.0506(9) 0.0408(8) -0.0152(7) -0.0027(6) -0.0070(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 C1 N1 1.496(6) . ? C1 C2 1.515(8) . ? C1 H1B 0.9900 . ? C1 H1A 0.9900 . ? C2 C3 1.500(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.517(7) . ? C3 H3B 0.9900 . ? C3 H3A 0.9900 . ? C4 N2 1.500(7) . ? C4 C5 1.508(9) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.500(8) . ? C5 H5B 0.9900 . ? C5 H5A 0.9900 . ? C6 N3 1.502(7) . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? C7 N3 1.506(7) . ? C7 C8 1.507(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.534(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N1 1.482(6) . ? C9 H9B 0.9900 . ? C9 H9A 0.9900 . ? C10 C11 1.504(8) . ? C10 N1 1.507(7) . ? C10 H10B 0.9900 . ? C10 H10A 0.9900 . ? C11 H11C 0.9800 . ? C11 H11B 0.9800 . ? C11 H11A 0.9800 . ? C20 F22 1.316(7) . ? C20 F20 1.333(7) . ? C20 F21 1.343(7) . ? C20 S20 1.810(6) . ? C30 F30 1.303(7) . ? C30 F31 1.314(7) . ? C30 F32 1.337(7) . ? C30 S30 1.796(6) . ? C40 F41 1.305(9) . ? C40 F42 1.310(9) . ? C40 F40 1.340(10) . ? C40 S40 1.810(9) . ? N1 H1D 0.9300 . ? N2 H2D 0.9200 . ? N2 H2E 0.9200 . ? N3 H3D 0.9200 . ? N3 H3E 0.9200 . ? O20 S20 1.425(4) . ? O21 S20 1.426(4) . ? O22 S20 1.433(4) . ? O30 S30 1.437(4) . ? O31 S30 1.426(3) . ? O32 S30 1.434(4) . ? O40 S40 1.378(5) . ? O41 S40 1.419(4) . ? O42 S40 1.438(4) . ? 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 N1 C1 C2 114.6(4) . . ? N1 C1 H1B 108.6 . . ? C2 C1 H1B 108.6 . . ? N1 C1 H1A 108.6 . . ? C2 C1 H1A 108.6 . . ? H1B C1 H1A 107.6 . . ? C3 C2 C1 115.3(5) . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2B 108.5 . . ? C1 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C2 C3 N2 115.5(4) . . ? C2 C3 H3B 108.4 . . ? N2 C3 H3B 108.4 . . ? C2 C3 H3A 108.4 . . ? N2 C3 H3A 108.4 . . ? H3B C3 H3A 107.5 . . ? N2 C4 C5 113.4(5) . . ? N2 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? N2 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 116.8(5) . . ? C6 C5 H5B 108.1 . . ? C4 C5 H5B 108.1 . . ? C6 C5 H5A 108.1 . . ? C4 C5 H5A 108.1 . . ? H5B C5 H5A 107.3 . . ? C5 C6 N3 112.9(4) . . ? C5 C6 H6B 109.0 . . ? N3 C6 H6B 109.0 . . ? C5 C6 H6A 109.0 . . ? N3 C6 H6A 109.0 . . ? H6B C6 H6A 107.8 . . ? N3 C7 C8 114.6(4) . . ? N3 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? N3 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C7 C8 C9 111.1(4) . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? N1 C9 C8 114.9(4) . . ? N1 C9 H9B 108.6 . . ? C8 C9 H9B 108.6 . . ? N1 C9 H9A 108.6 . . ? C8 C9 H9A 108.6 . . ? H9B C9 H9A 107.5 . . ? C11 C10 N1 112.8(4) . . ? C11 C10 H10B 109.0 . . ? N1 C10 H10B 109.0 . . ? C11 C10 H10A 109.0 . . ? N1 C10 H10A 109.0 . . ? H10B C10 H10A 107.8 . . ? C10 C11 H11C 109.5 . . ? C10 C11 H11B 109.5 . . ? H11C C11 H11B 109.5 . . ? C10 C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? H11B C11 H11A 109.5 . . ? F22 C20 F20 108.4(5) . . ? F22 C20 F21 107.6(5) . . ? F20 C20 F21 107.6(5) . . ? F22 C20 S20 111.3(4) . . ? F20 C20 S20 111.2(4) . . ? F21 C20 S20 110.6(4) . . ? F30 C30 F31 107.3(5) . . ? F30 C30 F32 107.6(5) . . ? F31 C30 F32 107.5(5) . . ? F30 C30 S30 112.0(4) . . ? F31 C30 S30 110.9(4) . . ? F32 C30 S30 111.2(4) . . ? F41 C40 F42 108.0(6) . . ? F41 C40 F40 105.4(8) . . ? F42 C40 F40 109.8(8) . . ? F41 C40 S40 112.2(6) . . ? F42 C40 S40 110.7(8) . . ? F40 C40 S40 110.7(5) . . ? C9 N1 C1 113.6(4) . . ? C9 N1 C10 111.6(4) . . ? C1 N1 C10 111.2(4) . . ? C9 N1 H1D 106.6 . . ? C1 N1 H1D 106.6 . . ? C10 N1 H1D 106.6 . . ? C4 N2 C3 114.6(5) . . ? C4 N2 H2D 108.6 . . ? C3 N2 H2D 108.6 . . ? C4 N2 H2E 108.6 . . ? C3 N2 H2E 108.6 . . ? H2D N2 H2E 107.6 . . ? C6 N3 C7 114.5(4) . . ? C6 N3 H3D 108.6 . . ? C7 N3 H3D 108.6 . . ? C6 N3 H3E 108.6 . . ? C7 N3 H3E 108.6 . . ? H3D N3 H3E 107.6 . . ? O20 S20 O21 114.7(3) . . ? O20 S20 O22 115.5(2) . . ? O21 S20 O22 113.7(3) . . ? O20 S20 C20 103.2(2) . . ? O21 S20 C20 103.2(3) . . ? O22 S20 C20 104.4(3) . . ? O31 S30 O32 113.6(2) . . ? O31 S30 O30 113.5(2) . . ? O32 S30 O30 115.0(2) . . ? O31 S30 C30 105.2(3) . . ? O32 S30 C30 104.1(2) . . ? O30 S30 C30 103.9(3) . . ? O40 S40 O41 117.8(5) . . ? O40 S40 O42 115.6(4) . . ? O41 S40 O42 112.2(3) . . ? O40 S40 C40 103.2(5) . . ? O41 S40 C40 102.1(3) . . ? O42 S40 C40 103.2(3) . . ? 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 N1 C1 C2 C3 -153.9(5) . . . . ? C1 C2 C3 N2 69.4(7) . . . . ? N2 C4 C5 C6 70.8(7) . . . . ? C4 C5 C6 N3 72.7(6) . . . . ? N3 C7 C8 C9 64.9(6) . . . . ? C7 C8 C9 N1 -167.8(4) . . . . ? C8 C9 N1 C1 68.2(6) . . . . ? C8 C9 N1 C10 -165.1(4) . . . . ? C2 C1 N1 C9 75.5(6) . . . . ? C2 C1 N1 C10 -51.4(6) . . . . ? C11 C10 N1 C9 65.5(6) . . . . ? C11 C10 N1 C1 -166.5(4) . . . . ? C5 C4 N2 C3 -162.4(5) . . . . ? C2 C3 N2 C4 58.1(7) . . . . ? C5 C6 N3 C7 -152.5(4) . . . . ? C8 C7 N3 C6 65.2(6) . . . . ? F22 C20 S20 O20 58.0(5) . . . . ? F20 C20 S20 O20 179.0(4) . . . . ? F21 C20 S20 O20 -61.6(4) . . . . ? F22 C20 S20 O21 -61.8(5) . . . . ? F20 C20 S20 O21 59.2(5) . . . . ? F21 C20 S20 O21 178.7(4) . . . . ? F22 C20 S20 O22 179.1(4) . . . . ? F20 C20 S20 O22 -59.9(5) . . . . ? F21 C20 S20 O22 59.6(4) . . . . ? F30 C30 S30 O31 60.4(5) . . . . ? F31 C30 S30 O31 -179.7(4) . . . . ? F32 C30 S30 O31 -60.1(4) . . . . ? F30 C30 S30 O32 -179.8(4) . . . . ? F31 C30 S30 O32 -60.0(5) . . . . ? F32 C30 S30 O32 59.6(4) . . . . ? F30 C30 S30 O30 -59.1(5) . . . . ? F31 C30 S30 O30 60.7(5) . . . . ? F32 C30 S30 O30 -179.7(4) . . . . ? F41 C40 S40 O40 59.4(7) . . . . ? F42 C40 S40 O40 -61.2(7) . . . . ? F40 C40 S40 O40 176.9(7) . . . . ? F41 C40 S40 O41 -63.3(7) . . . . ? F42 C40 S40 O41 176.1(6) . . . . ? F40 C40 S40 O41 54.2(7) . . . . ? F41 C40 S40 O42 -179.9(6) . . . . ? F42 C40 S40 O42 59.5(6) . . . . ? F40 C40 S40 O42 -62.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 66.46 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.466 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.084 data_am090104 _database_code_depnum_ccdc_archive 'CCDC 661098' #TrackingRef 'web_deposit_cif_file_1_BernhardSpingler_1312475951.L.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H50 F12 N6 O12 S4' _chemical_formula_weight 982.95 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 14.5787(11) _cell_length_b 10.7388(8) _cell_length_c 15.1058(12) _cell_angle_alpha 91.857(9) _cell_angle_beta 117.268(8) _cell_angle_gamma 87.518(9) _cell_volume 2099.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020 _exptl_absorpt_coefficient_mu 0.340 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8932 _exptl_absorpt_correction_T_max 0.9539 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '/f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 13 _diffrn_standards_decay_% ? _diffrn_reflns_number 36077 _diffrn_reflns_av_R_equivalents 0.1039 _diffrn_reflns_av_sigmaI/netI 0.0656 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 28.28 _reflns_number_total 9617 _reflns_number_gt 6837 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _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^)+(0.1756P)^2^+0.2981P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.023(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9617 _refine_ls_number_parameters 604 _refine_ls_number_restraints 135 _refine_ls_R_factor_all 0.0992 _refine_ls_R_factor_gt 0.0814 _refine_ls_wR_factor_ref 0.2676 _refine_ls_wR_factor_gt 0.2480 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.117 _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 C1 C 0.8434(3) 0.1194(3) 0.6610(2) 0.0494(7) Uani 1 1 d . . . H1B H 0.8748 0.1103 0.6152 0.059 Uiso 1 1 calc R . . H1A H 0.7772 0.1670 0.6260 0.059 Uiso 1 1 calc R . . C2 C 0.8214(3) -0.0103(3) 0.6843(3) 0.0543(7) Uani 1 1 d . . . H2B H 0.8867 -0.0606 0.7119 0.065 Uiso 1 1 calc R . . H2A H 0.7733 -0.0507 0.6210 0.065 Uiso 1 1 calc R . . C3 C 0.7753(3) -0.0141(3) 0.7571(2) 0.0532(7) Uani 1 1 d . . . H3A H 0.7586 -0.1010 0.7626 0.064 Uiso 1 1 calc R . . H3B H 0.8270 0.0141 0.8239 0.064 Uiso 1 1 calc R . . C4 C 0.6400(3) 0.0878(4) 0.7987(3) 0.0575(8) Uani 1 1 d . . . H4B H 0.6986 0.0877 0.8667 0.069 Uiso 1 1 calc R . . H4A H 0.5943 0.0195 0.7936 0.069 Uiso 1 1 calc R . . C5 C 0.5804(3) 0.2121(4) 0.7800(3) 0.0607(8) Uani 1 1 d . . . H5A H 0.5455 0.2188 0.8230 0.073 Uiso 1 1 calc R . . H5B H 0.5263 0.2141 0.7099 0.073 Uiso 1 1 calc R . . C6 C 0.6490(3) 0.3251(4) 0.8007(3) 0.0589(8) Uani 1 1 d . . . H6A H 0.6063 0.4029 0.7890 0.071 Uiso 1 1 calc R . . H6B H 0.7021 0.3251 0.8712 0.071 Uiso 1 1 calc R . . C7 C 0.7768(3) 0.4186(3) 0.7600(2) 0.0518(7) Uani 1 1 d . . . H7A H 0.8299 0.4099 0.8301 0.062 Uiso 1 1 calc R . . H7B H 0.7424 0.5018 0.7528 0.062 Uiso 1 1 calc R . . C8 C 0.8283(3) 0.4080(3) 0.6917(3) 0.0562(8) Uani 1 1 d . . . H8B H 0.7771 0.3762 0.6260 0.067 Uiso 1 1 calc R . . H8A H 0.8454 0.4929 0.6817 0.067 Uiso 1 1 calc R . . C9 C 0.9250(3) 0.3261(3) 0.7261(3) 0.0550(7) Uani 1 1 d . . . H9B H 0.9805 0.3658 0.7854 0.066 Uiso 1 1 calc R . . H9A H 0.9468 0.3224 0.6729 0.066 Uiso 1 1 calc R . . C10 C 1.0178(2) 0.1288(3) 0.8114(2) 0.0505(7) Uani 1 1 d . . . H10B H 1.0073 0.0517 0.8393 0.061 Uiso 1 1 calc R . . H10A H 1.0608 0.1837 0.8680 0.061 Uiso 1 1 calc R . . C11 C 1.0768(3) 0.0947(3) 0.7522(3) 0.0556(7) Uani 1 1 d . . . H11B H 1.0401 0.0307 0.7006 0.067 Uiso 1 1 calc R . . H11A H 1.0841 0.1691 0.7192 0.067 Uiso 1 1 calc R . . C12 C 1.1808(3) 0.0448(4) 0.8266(3) 0.0592(8) Uani 1 1 d . . . H12A H 1.1705 -0.0153 0.8693 0.071 Uiso 1 1 calc R . . H12B H 1.2198 0.1147 0.8700 0.071 Uiso 1 1 calc R . . C13 C 1.2645(3) 0.0696(4) 0.7169(3) 0.0622(9) Uani 1 1 d . . . H13A H 1.2963 0.1452 0.7566 0.075 Uiso 1 1 calc R . . H13B H 1.1967 0.0955 0.6623 0.075 Uiso 1 1 calc R . . C14 C 1.3333(3) 0.0183(4) 0.6703(3) 0.0639(9) Uani 1 1 d . . . H14A H 1.3392 0.0845 0.6292 0.077 Uiso 1 1 calc R . . H14B H 1.4033 0.0006 0.7249 0.077 Uiso 1 1 calc R . . C15 C 1.2970(3) -0.0993(4) 0.6057(3) 0.0618(9) Uani 1 1 d . . . H15B H 1.2209 -0.1028 0.5770 0.074 Uiso 1 1 calc R . . H15A H 1.3147 -0.0957 0.5499 0.074 Uiso 1 1 calc R . . C16 C 1.3035(4) -0.3283(4) 0.6030(3) 0.0724(11) Uani 1 1 d . . . H16B H 1.3287 -0.3373 0.5523 0.087 Uiso 1 1 calc R . . H16A H 1.2272 -0.3210 0.5678 0.087 Uiso 1 1 calc R . . C17 C 1.3375(4) -0.4452(5) 0.6695(4) 0.0819(13) Uani 1 1 d . . . H17B H 1.3137 -0.5205 0.6266 0.098 Uiso 1 1 calc R . . H17A H 1.4138 -0.4507 0.7056 0.098 Uiso 1 1 calc R . . C18 C 1.2950(5) -0.4432(5) 0.7449(4) 0.0904(14) Uani 1 1 d . . . H18B H 1.2189 -0.4315 0.7104 0.109 Uiso 1 1 calc R . . H18A H 1.3124 -0.5232 0.7808 0.109 Uiso 1 1 calc R . . C19 C 1.2844(4) -0.2879(5) 0.8701(3) 0.0781(12) Uani 1 1 d . . . H19A H 1.2843 -0.3513 0.9161 0.094 Uiso 1 1 calc R . . H19B H 1.2119 -0.2683 0.8215 0.094 Uiso 1 1 calc R . . C20 C 1.3339(4) -0.1710(5) 0.9285(3) 0.0773(12) Uani 1 1 d . . . H20A H 1.4030 -0.1944 0.9823 0.093 Uiso 1 1 calc R . . H20B H 1.2918 -0.1372 0.9603 0.093 Uiso 1 1 calc R . . C21 C 1.3461(3) -0.0677(4) 0.8676(3) 0.0662(10) Uani 1 1 d . . . H21A H 1.3804 0.0028 0.9131 0.079 Uiso 1 1 calc R . . H21B H 1.3922 -0.0996 0.8396 0.079 Uiso 1 1 calc R . . C30 C 0.6008(3) -0.3299(4) 0.5645(3) 0.0654(9) Uani 1 1 d . . . C40 C 0.9391(4) -0.3291(5) 0.5618(4) 0.0787(12) Uani 1 1 d . . . C50 C 0.6902(7) -0.2984(7) 0.9238(4) 0.121(3) Uani 1 1 d . . . N1 N 0.9145(2) 0.1932(2) 0.75224(19) 0.0470(6) Uani 1 1 d . . . H1C H 0.8829 0.1995 0.7935 0.056 Uiso 1 1 calc R . . N2 N 0.6795(2) 0.0673(3) 0.7236(2) 0.0519(6) Uani 1 1 d . . . H2C H 0.6926 0.1436 0.7065 0.062 Uiso 1 1 calc R . . H2D H 0.6283 0.0322 0.6671 0.062 Uiso 1 1 calc R . . N3 N 0.7002(2) 0.3216(3) 0.7352(2) 0.0501(6) Uani 1 1 d D . . H3C H 0.656(3) 0.340(4) 0.6704(17) 0.063(11) Uiso 1 1 d D . . N4 N 1.2463(2) -0.0191(3) 0.7831(2) 0.0536(6) Uani 1 1 d . . . H4C H 1.2107 -0.0866 0.7443 0.064 Uiso 1 1 calc R . . N5 N 1.3452(3) -0.2141(3) 0.6639(2) 0.0631(8) Uani 1 1 d D . . H5C H 1.4147(17) -0.224(4) 0.682(3) 0.063(11) Uiso 1 1 d D . . N6 N 1.3421(3) -0.3382(4) 0.8167(3) 0.0769(10) Uani 1 1 d . . . H6C H 1.4067 -0.3644 0.8634 0.092 Uiso 1 1 calc R . . H6D H 1.3507 -0.2740 0.7826 0.092 Uiso 1 1 calc R . . O30 O 0.5799(3) -0.1078(3) 0.4995(3) 0.0797(9) Uani 1 1 d . . . O31 O 0.5400(2) -0.1435(3) 0.63582(18) 0.0617(6) Uani 1 1 d . . . O32 O 0.42526(19) -0.2164(3) 0.46895(17) 0.0607(6) Uani 1 1 d . . . O40 O 1.0311(3) -0.2310(3) 0.4718(2) 0.0761(8) Uani 1 1 d . . . O41 O 0.9294(2) -0.0950(3) 0.5276(2) 0.0744(7) Uani 1 1 d . . . O42 O 1.0938(2) -0.1866(3) 0.64774(19) 0.0645(7) Uani 1 1 d . . . O50 O 0.6963(7) -0.3190(7) 1.0893(4) 0.183(4) Uani 1 1 d . . . O51 O 0.5801(5) -0.1934(7) 0.9865(10) 0.261(6) Uani 1 1 d . . . O52 O 0.5573(4) -0.4114(5) 0.9491(5) 0.142(2) Uani 1 1 d . . . F30 F 0.5964(3) -0.3822(3) 0.4819(3) 0.1092(11) Uani 1 1 d . . . F31 F 0.5643(2) -0.4115(2) 0.6039(2) 0.0900(9) Uani 1 1 d . . . F32 F 0.70069(19) -0.3134(2) 0.6290(2) 0.0854(8) Uani 1 1 d . . . F40 F 0.9008(3) -0.3054(3) 0.6248(4) 0.1234(14) Uani 1 1 d . . . F41 F 1.0007(3) -0.4300(3) 0.5929(3) 0.1029(10) Uani 1 1 d . . . F42 F 0.8618(3) -0.3600(4) 0.4738(4) 0.1436(17) Uani 1 1 d . . . F50 F 0.7548(5) -0.2014(5) 0.9527(3) 0.1516(19) Uani 1 1 d . . . F51 F 0.6492(7) -0.3027(7) 0.8331(3) 0.209(3) Uani 1 1 d . . . F52 F 0.7474(6) -0.4059(7) 0.9339(6) 0.204(3) Uani 1 1 d . . . S30 S 0.52848(6) -0.18229(7) 0.53920(5) 0.0473(2) Uani 1 1 d . . . S40 S 1.00525(7) -0.19511(8) 0.55007(6) 0.0554(3) Uani 1 1 d . . . S50 S 0.62584(12) -0.31037(17) 0.99555(14) 0.1042(5) Uani 1 1 d . . . S60 S 1.04843(8) -0.19342(9) 0.96786(6) 0.0592(3) Uani 1 1 d D . . C60 C 0.9948(9) -0.3463(10) 0.9203(6) 0.117(4) Uani 0.70 1 d PD A 1 F60 F 0.9586(6) -0.3910(7) 0.9774(5) 0.150(2) Uani 0.70 1 d PDU A 1 F61 F 0.9181(6) -0.3402(7) 0.8324(5) 0.152(2) Uani 0.70 1 d PDU A 1 F62 F 1.0738(8) -0.4208(7) 0.9222(6) 0.136(2) Uani 0.70 1 d PDU A 1 O60 O 1.0896(7) -0.1555(6) 0.9067(5) 0.110(2) Uani 0.70 1 d P A 1 O61 O 1.1086(4) -0.2123(5) 1.0704(3) 0.0732(13) Uani 0.70 1 d P A 1 O62 O 0.9552(5) -0.1160(6) 0.9487(4) 0.0960(18) Uani 0.70 1 d P A 1 F65 F 1.0316(10) -0.3273(11) 0.8114(6) 0.115(2) Uani 0.30 1 d PDU A 2 O63 O 1.1475(6) -0.1501(9) 0.9744(6) 0.0584(18) Uani 0.30 1 d PDU A 2 O64 O 1.0604(7) -0.2397(10) 1.0605(6) 0.058(2) Uani 0.30 1 d PDU A 2 C61 C 1.0381(9) -0.3417(11) 0.9000(8) 0.061(3) Uani 0.30 1 d PD A 2 F64 F 0.9603(11) -0.4114(12) 0.8929(10) 0.118(3) Uani 0.30 1 d PDU A 2 F63 F 1.1258(10) -0.4121(12) 0.9561(9) 0.113(3) Uani 0.30 1 d PDU A 2 O65 O 0.9610(8) -0.1346(12) 0.9020(8) 0.075(3) Uani 0.30 1 d PDU A 2 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 C1 0.0491(16) 0.0481(15) 0.0484(14) -0.0039(12) 0.0205(12) -0.0008(14) C2 0.0553(18) 0.0435(15) 0.0586(17) -0.0032(12) 0.0219(14) 0.0017(14) C3 0.0484(17) 0.0465(15) 0.0573(16) 0.0042(12) 0.0176(13) -0.0016(14) C4 0.0529(18) 0.065(2) 0.0546(16) 0.0009(14) 0.0242(14) -0.0084(16) C5 0.0510(18) 0.071(2) 0.0605(18) -0.0049(16) 0.0262(15) -0.0036(17) C6 0.0544(18) 0.0620(19) 0.0593(18) -0.0078(15) 0.0258(15) 0.0001(17) C7 0.0538(17) 0.0409(14) 0.0540(16) -0.0004(12) 0.0193(13) 0.0040(14) C8 0.065(2) 0.0459(15) 0.0552(16) 0.0045(13) 0.0253(15) -0.0017(15) C9 0.063(2) 0.0457(15) 0.0628(18) -0.0001(13) 0.0338(16) -0.0047(15) C10 0.0455(15) 0.0527(16) 0.0512(15) -0.0012(12) 0.0208(12) 0.0016(14) C11 0.0503(17) 0.0588(18) 0.0577(17) -0.0020(14) 0.0255(14) 0.0032(16) C12 0.0502(17) 0.073(2) 0.0544(17) -0.0036(15) 0.0246(14) 0.0021(17) C13 0.058(2) 0.064(2) 0.071(2) -0.0063(17) 0.0353(17) -0.0063(18) C14 0.0550(19) 0.075(2) 0.071(2) -0.0057(18) 0.0367(17) -0.0087(18) C15 0.0506(17) 0.080(2) 0.0593(18) -0.0056(17) 0.0296(15) -0.0041(18) C16 0.073(2) 0.081(3) 0.073(2) -0.020(2) 0.042(2) -0.014(2) C17 0.091(3) 0.073(3) 0.091(3) -0.017(2) 0.050(3) -0.011(2) C18 0.106(4) 0.078(3) 0.102(3) -0.008(3) 0.059(3) -0.019(3) C19 0.081(3) 0.091(3) 0.076(2) 0.022(2) 0.048(2) 0.017(3) C20 0.068(2) 0.105(3) 0.0576(19) 0.011(2) 0.0289(18) 0.029(3) C21 0.0449(17) 0.088(3) 0.0561(18) -0.0106(17) 0.0158(14) 0.0068(19) C30 0.058(2) 0.0506(18) 0.083(2) 0.0040(17) 0.0284(18) 0.0047(17) C40 0.076(3) 0.069(2) 0.099(3) -0.006(2) 0.046(2) -0.017(2) C50 0.176(7) 0.113(5) 0.075(3) -0.024(3) 0.058(4) -0.032(5) N1 0.0468(13) 0.0454(12) 0.0494(12) -0.0002(10) 0.0225(10) -0.0004(11) N2 0.0478(14) 0.0499(13) 0.0524(13) -0.0002(11) 0.0182(11) -0.0005(12) N3 0.0482(14) 0.0498(13) 0.0474(12) -0.0021(10) 0.0179(11) 0.0012(12) N4 0.0415(13) 0.0649(16) 0.0520(13) -0.0077(12) 0.0199(11) -0.0018(13) N5 0.0560(17) 0.075(2) 0.0634(16) -0.0128(15) 0.0314(14) -0.0104(16) N6 0.088(3) 0.075(2) 0.080(2) -0.0007(18) 0.050(2) -0.002(2) O30 0.0785(19) 0.0678(17) 0.113(2) 0.0317(16) 0.0608(18) 0.0108(16) O31 0.0534(13) 0.0727(16) 0.0507(12) -0.0103(11) 0.0175(10) 0.0005(12) O32 0.0497(13) 0.0706(15) 0.0481(11) -0.0055(10) 0.0117(10) 0.0058(12) O40 0.084(2) 0.092(2) 0.0629(15) -0.0095(14) 0.0421(15) -0.0085(17) O41 0.0679(17) 0.0682(17) 0.0863(19) 0.0058(14) 0.0350(15) 0.0052(15) O42 0.0644(15) 0.0675(15) 0.0593(13) -0.0074(11) 0.0262(12) -0.0113(13) O50 0.266(9) 0.205(7) 0.097(3) -0.022(4) 0.092(4) -0.118(7) O51 0.099(4) 0.156(6) 0.510(16) -0.174(9) 0.133(7) -0.029(4) O52 0.105(3) 0.120(4) 0.194(5) -0.036(4) 0.061(4) -0.037(3) F30 0.121(3) 0.0879(19) 0.130(3) -0.0262(19) 0.071(2) 0.021(2) F31 0.0752(17) 0.0579(13) 0.121(2) 0.0262(13) 0.0293(15) -0.0053(13) F32 0.0494(12) 0.0628(14) 0.125(2) 0.0217(14) 0.0242(13) 0.0142(12) F40 0.148(3) 0.099(2) 0.189(4) 0.005(2) 0.132(3) -0.020(2) F41 0.128(3) 0.0572(14) 0.134(3) 0.0000(15) 0.069(2) -0.0102(17) F42 0.097(2) 0.135(3) 0.161(3) -0.032(3) 0.023(2) -0.063(3) F50 0.203(5) 0.167(4) 0.117(3) -0.021(3) 0.098(3) -0.074(4) F51 0.305(9) 0.205(6) 0.085(3) -0.025(3) 0.061(4) -0.036(6) F52 0.197(6) 0.180(5) 0.279(8) -0.108(6) 0.154(6) -0.020(5) S30 0.0433(4) 0.0473(4) 0.0498(4) 0.0032(3) 0.0204(3) 0.0029(3) S40 0.0561(5) 0.0583(5) 0.0557(4) -0.0052(3) 0.0288(4) -0.0091(4) S50 0.0819(9) 0.1137(12) 0.1258(12) -0.0370(10) 0.0559(9) -0.0203(8) S60 0.0613(5) 0.0637(5) 0.0505(4) 0.0070(3) 0.0233(4) -0.0033(4) C60 0.151(11) 0.123(8) 0.075(5) -0.004(5) 0.051(6) 0.007(8) F60 0.180(4) 0.127(3) 0.138(4) -0.003(3) 0.064(4) -0.068(3) F61 0.176(4) 0.131(4) 0.121(4) -0.040(3) 0.042(3) -0.063(3) F62 0.184(5) 0.092(3) 0.132(4) -0.044(3) 0.073(4) -0.029(4) O60 0.166(6) 0.088(3) 0.124(5) 0.019(3) 0.107(5) -0.002(4) O61 0.070(3) 0.080(3) 0.049(2) -0.0049(19) 0.012(2) 0.018(3) O62 0.077(3) 0.105(4) 0.077(3) 0.014(3) 0.014(3) 0.037(3) F65 0.169(5) 0.123(4) 0.074(4) -0.044(3) 0.072(4) -0.056(4) O63 0.046(4) 0.075(5) 0.048(3) 0.000(3) 0.016(3) -0.014(3) O64 0.051(4) 0.074(5) 0.048(4) -0.003(3) 0.021(3) -0.006(4) C61 0.065(8) 0.065(8) 0.057(7) -0.020(6) 0.033(6) -0.005(7) F64 0.159(5) 0.091(4) 0.108(5) -0.044(4) 0.061(4) -0.079(4) F63 0.154(6) 0.093(4) 0.106(5) -0.052(4) 0.071(4) -0.052(4) O65 0.060(5) 0.079(5) 0.058(5) 0.017(4) 0.005(4) 0.005(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 C1 N1 1.515(4) . ? C1 C2 1.530(5) . ? C1 H1B 0.9900 . ? C1 H1A 0.9900 . ? C2 C3 1.532(5) . ? C2 H2B 0.9900 . ? C2 H2A 0.9900 . ? C3 N2 1.499(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.496(4) . ? C4 C5 1.521(6) . ? C4 H4B 0.9900 . ? C4 H4A 0.9900 . ? C5 C6 1.538(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N3 1.486(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N3 1.470(4) . ? C7 C8 1.528(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.510(5) . ? C8 H8B 0.9900 . ? C8 H8A 0.9900 . ? C9 N1 1.526(4) . ? C9 H9B 0.9900 . ? C9 H9A 0.9900 . ? C10 N1 1.503(4) . ? C10 C11 1.526(4) . ? C10 H10B 0.9900 . ? C10 H10A 0.9900 . ? C11 C12 1.503(5) . ? C11 H11B 0.9900 . ? C11 H11A 0.9900 . ? C12 N4 1.517(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N4 1.518(5) . ? C13 C14 1.542(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.527(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N5 1.489(6) . ? C15 H15B 0.9900 . ? C15 H15A 0.9900 . ? C16 N5 1.483(5) . ? C16 C17 1.550(7) . ? C16 H16B 0.9900 . ? C16 H16A 0.9900 . ? C17 C18 1.525(7) . ? C17 H17B 0.9900 . ? C17 H17A 0.9900 . ? C18 N6 1.491(6) . ? C18 H18B 0.9900 . ? C18 H18A 0.9900 . ? C19 N6 1.485(6) . ? C19 C20 1.515(8) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.530(7) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 N4 1.515(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C30 F30 1.327(5) . ? C30 F31 1.330(5) . ? C30 F32 1.346(5) . ? C30 S30 1.816(4) . ? C40 F40 1.320(6) . ? C40 F41 1.328(6) . ? C40 F42 1.334(6) . ? C40 S40 1.823(4) . ? C50 F51 1.218(7) . ? C50 F50 1.357(8) . ? C50 F52 1.366(10) . ? C50 S50 1.739(8) . ? N1 H1C 0.9300 . ? N2 H2C 0.9200 . ? N2 H2D 0.9200 . ? N3 H3C 0.916(19) . ? N4 H4C 0.9300 . ? N5 H5C 0.92(2) . ? N6 H6C 0.9200 . ? N6 H6D 0.9200 . ? O30 S30 1.435(3) . ? O31 S30 1.440(2) . ? O32 S30 1.444(2) . ? O40 S40 1.433(3) . ? O41 S40 1.439(3) . ? O42 S40 1.452(3) . ? O50 S50 1.317(7) . ? O51 S50 1.377(8) . ? O52 S50 1.439(5) . ? S60 O65 1.350(9) . ? S60 O60 1.390(5) . ? S60 O61 1.404(4) . ? S60 O64 1.432(8) . ? S60 O62 1.476(6) . ? S60 O63 1.496(7) . ? S60 C60 1.828(11) . ? S60 C61 1.839(11) . ? C60 F61 1.287(10) . ? C60 F60 1.311(10) . ? C60 F62 1.363(10) . ? F65 C61 1.312(11) . ? C61 F64 1.347(12) . ? C61 F63 1.375(13) . ? 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 N1 C1 C2 113.8(3) . . ? N1 C1 H1B 108.8 . . ? C2 C1 H1B 108.8 . . ? N1 C1 H1A 108.8 . . ? C2 C1 H1A 108.8 . . ? H1B C1 H1A 107.7 . . ? C1 C2 C3 115.9(3) . . ? C1 C2 H2B 108.3 . . ? C3 C2 H2B 108.3 . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2A 108.3 . . ? H2B C2 H2A 107.4 . . ? N2 C3 C2 111.4(3) . . ? N2 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? N2 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? N2 C4 C5 109.6(3) . . ? N2 C4 H4B 109.7 . . ? C5 C4 H4B 109.7 . . ? N2 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? H4B C4 H4A 108.2 . . ? C4 C5 C6 113.3(3) . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? N3 C6 C5 111.0(3) . . ? N3 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? N3 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N3 C7 C8 110.8(2) . . ? N3 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C9 C8 C7 117.0(3) . . ? C9 C8 H8B 108.0 . . ? C7 C8 H8B 108.0 . . ? C9 C8 H8A 108.0 . . ? C7 C8 H8A 108.0 . . ? H8B C8 H8A 107.3 . . ? C8 C9 N1 115.2(3) . . ? C8 C9 H9B 108.5 . . ? N1 C9 H9B 108.5 . . ? C8 C9 H9A 108.5 . . ? N1 C9 H9A 108.5 . . ? H9B C9 H9A 107.5 . . ? N1 C10 C11 114.6(3) . . ? N1 C10 H10B 108.6 . . ? C11 C10 H10B 108.6 . . ? N1 C10 H10A 108.6 . . ? C11 C10 H10A 108.6 . . ? H10B C10 H10A 107.6 . . ? C12 C11 C10 105.9(3) . . ? C12 C11 H11B 110.6 . . ? C10 C11 H11B 110.6 . . ? C12 C11 H11A 110.6 . . ? C10 C11 H11A 110.6 . . ? H11B C11 H11A 108.7 . . ? C11 C12 N4 115.7(3) . . ? C11 C12 H12A 108.4 . . ? N4 C12 H12A 108.4 . . ? C11 C12 H12B 108.4 . . ? N4 C12 H12B 108.4 . . ? H12A C12 H12B 107.4 . . ? N4 C13 C14 116.1(3) . . ? N4 C13 H13A 108.3 . . ? C14 C13 H13A 108.3 . . ? N4 C13 H13B 108.3 . . ? C14 C13 H13B 108.3 . . ? H13A C13 H13B 107.4 . . ? C15 C14 C13 116.2(3) . . ? C15 C14 H14A 108.2 . . ? C13 C14 H14A 108.2 . . ? C15 C14 H14B 108.2 . . ? C13 C14 H14B 108.2 . . ? H14A C14 H14B 107.4 . . ? N5 C15 C14 111.7(3) . . ? N5 C15 H15B 109.3 . . ? C14 C15 H15B 109.3 . . ? N5 C15 H15A 109.3 . . ? C14 C15 H15A 109.3 . . ? H15B C15 H15A 107.9 . . ? N5 C16 C17 110.6(4) . . ? N5 C16 H16B 109.5 . . ? C17 C16 H16B 109.5 . . ? N5 C16 H16A 109.5 . . ? C17 C16 H16A 109.5 . . ? H16B C16 H16A 108.1 . . ? C18 C17 C16 112.9(4) . . ? C18 C17 H17B 109.0 . . ? C16 C17 H17B 109.0 . . ? C18 C17 H17A 109.0 . . ? C16 C17 H17A 109.0 . . ? H17B C17 H17A 107.8 . . ? N6 C18 C17 108.2(4) . . ? N6 C18 H18B 110.1 . . ? C17 C18 H18B 110.0 . . ? N6 C18 H18A 110.1 . . ? C17 C18 H18A 110.1 . . ? H18B C18 H18A 108.4 . . ? N6 C19 C20 110.3(4) . . ? N6 C19 H19A 109.6 . . ? C20 C19 H19A 109.6 . . ? N6 C19 H19B 109.6 . . ? C20 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? C19 C20 C21 115.3(3) . . ? C19 C20 H20A 108.4 . . ? C21 C20 H20A 108.4 . . ? C19 C20 H20B 108.4 . . ? C21 C20 H20B 108.4 . . ? H20A C20 H20B 107.5 . . ? N4 C21 C20 115.0(3) . . ? N4 C21 H21A 108.5 . . ? C20 C21 H21A 108.5 . . ? N4 C21 H21B 108.5 . . ? C20 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? F30 C30 F31 106.9(4) . . ? F30 C30 F32 108.2(4) . . ? F31 C30 F32 107.8(4) . . ? F30 C30 S30 111.4(3) . . ? F31 C30 S30 111.8(3) . . ? F32 C30 S30 110.5(3) . . ? F40 C40 F41 107.8(4) . . ? F40 C40 F42 108.2(5) . . ? F41 C40 F42 106.0(4) . . ? F40 C40 S40 111.3(3) . . ? F41 C40 S40 112.5(3) . . ? F42 C40 S40 110.7(4) . . ? F51 C50 F50 106.9(7) . . ? F51 C50 F52 93.9(6) . . ? F50 C50 F52 108.3(8) . . ? F51 C50 S50 124.8(8) . . ? F50 C50 S50 112.6(4) . . ? F52 C50 S50 108.0(6) . . ? C10 N1 C1 113.2(2) . . ? C10 N1 C9 112.1(3) . . ? C1 N1 C9 111.6(2) . . ? C10 N1 H1C 106.5 . . ? C1 N1 H1C 106.5 . . ? C9 N1 H1C 106.5 . . ? C4 N2 C3 115.1(3) . . ? C4 N2 H2C 108.5 . . ? C3 N2 H2C 108.5 . . ? C4 N2 H2D 108.5 . . ? C3 N2 H2D 108.5 . . ? H2C N2 H2D 107.5 . . ? C7 N3 C6 113.4(2) . . ? C7 N3 H3C 101(3) . . ? C6 N3 H3C 113(3) . . ? C21 N4 C12 108.8(3) . . ? C21 N4 C13 112.4(3) . . ? C12 N4 C13 110.5(3) . . ? C21 N4 H4C 108.4 . . ? C12 N4 H4C 108.4 . . ? C13 N4 H4C 108.4 . . ? C16 N5 C15 111.5(3) . . ? C16 N5 H5C 102(3) . . ? C15 N5 H5C 113(3) . . ? C19 N6 C18 116.8(4) . . ? C19 N6 H6C 108.1 . . ? C18 N6 H6C 108.1 . . ? C19 N6 H6D 108.1 . . ? C18 N6 H6D 108.1 . . ? H6C N6 H6D 107.3 . . ? O30 S30 O31 115.2(2) . . ? O30 S30 O32 115.09(19) . . ? O31 S30 O32 114.60(16) . . ? O30 S30 C30 103.42(19) . . ? O31 S30 C30 102.86(19) . . ? O32 S30 C30 103.19(18) . . ? O40 S40 O41 115.8(2) . . ? O40 S40 O42 114.00(19) . . ? O41 S40 O42 114.81(18) . . ? O40 S40 C40 104.0(2) . . ? O41 S40 C40 103.2(2) . . ? O42 S40 C40 102.7(2) . . ? O50 S50 O51 105.9(6) . . ? O50 S50 O52 119.6(4) . . ? O51 S50 O52 116.3(4) . . ? O50 S50 C50 107.5(4) . . ? O51 S50 C50 102.0(6) . . ? O52 S50 C50 103.8(3) . . ? O65 S60 O60 84.8(6) . . ? O65 S60 O61 141.6(6) . . ? O60 S60 O61 122.9(5) . . ? O65 S60 O64 122.7(6) . . ? O60 S60 O64 151.2(5) . . ? O61 S60 O64 29.5(3) . . ? O65 S60 O62 31.1(5) . . ? O60 S60 O62 109.3(4) . . ? O61 S60 O62 110.5(3) . . ? O64 S60 O62 94.5(5) . . ? O65 S60 O63 116.6(6) . . ? O60 S60 O63 39.7(4) . . ? O61 S60 O63 83.4(4) . . ? O64 S60 O63 112.6(5) . . ? O62 S60 O63 126.9(5) . . ? O65 S60 C60 91.7(6) . . ? O60 S60 C60 106.0(4) . . ? O61 S60 C60 103.5(4) . . ? O64 S60 C60 83.4(5) . . ? O62 S60 C60 102.3(5) . . ? O63 S60 C60 124.7(5) . . ? O65 S60 C61 99.4(7) . . ? O60 S60 C61 82.2(4) . . ? O61 S60 C61 109.6(4) . . ? O64 S60 C61 99.7(6) . . ? O62 S60 C61 120.5(5) . . ? O63 S60 C61 99.6(5) . . ? C60 S60 C61 25.9(4) . . ? F61 C60 F60 105.9(10) . . ? F61 C60 F62 111.9(9) . . ? F60 C60 F62 110.7(9) . . ? F61 C60 S60 112.1(8) . . ? F60 C60 S60 109.6(6) . . ? F62 C60 S60 106.6(7) . . ? F65 C61 F64 109.9(9) . . ? F65 C61 F63 108.6(10) . . ? F64 C61 F63 104.3(10) . . ? F65 C61 S60 113.1(9) . . ? F64 C61 S60 113.5(9) . . ? F63 C61 S60 106.9(8) . . ? 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 N1 C1 C2 C3 56.7(4) . . . . ? C1 C2 C3 N2 54.3(4) . . . . ? N2 C4 C5 C6 -67.4(4) . . . . ? C4 C5 C6 N3 60.7(4) . . . . ? N3 C7 C8 C9 -90.1(3) . . . . ? C7 C8 C9 N1 53.8(4) . . . . ? N1 C10 C11 C12 174.1(3) . . . . ? C10 C11 C12 N4 168.4(3) . . . . ? N4 C13 C14 C15 58.0(5) . . . . ? C13 C14 C15 N5 -93.9(4) . . . . ? N5 C16 C17 C18 63.4(5) . . . . ? C16 C17 C18 N6 -65.6(6) . . . . ? N6 C19 C20 C21 55.3(5) . . . . ? C19 C20 C21 N4 59.6(5) . . . . ? C11 C10 N1 C1 56.1(3) . . . . ? C11 C10 N1 C9 -71.2(3) . . . . ? C2 C1 N1 C10 58.3(4) . . . . ? C2 C1 N1 C9 -174.1(3) . . . . ? C8 C9 N1 C10 -164.3(3) . . . . ? C8 C9 N1 C1 67.5(3) . . . . ? C5 C4 N2 C3 153.0(3) . . . . ? C2 C3 N2 C4 -169.4(3) . . . . ? C8 C7 N3 C6 178.7(3) . . . . ? C5 C6 N3 C7 -172.8(3) . . . . ? C20 C21 N4 C12 65.4(4) . . . . ? C20 C21 N4 C13 -171.9(3) . . . . ? C11 C12 N4 C21 -177.9(3) . . . . ? C11 C12 N4 C13 58.2(4) . . . . ? C14 C13 N4 C21 56.3(4) . . . . ? C14 C13 N4 C12 178.0(3) . . . . ? C17 C16 N5 C15 -168.5(3) . . . . ? C14 C15 N5 C16 175.4(3) . . . . ? C20 C19 N6 C18 -172.0(4) . . . . ? C17 C18 N6 C19 156.8(5) . . . . ? F30 C30 S30 O30 -61.4(4) . . . . ? F31 C30 S30 O30 179.0(3) . . . . ? F32 C30 S30 O30 58.9(4) . . . . ? F30 C30 S30 O31 178.3(3) . . . . ? F31 C30 S30 O31 58.7(3) . . . . ? F32 C30 S30 O31 -61.3(3) . . . . ? F30 C30 S30 O32 58.9(3) . . . . ? F31 C30 S30 O32 -60.7(3) . . . . ? F32 C30 S30 O32 179.2(3) . . . . ? F40 C40 S40 O40 -173.6(4) . . . . ? F41 C40 S40 O40 65.2(4) . . . . ? F42 C40 S40 O40 -53.2(4) . . . . ? F40 C40 S40 O41 -52.3(4) . . . . ? F41 C40 S40 O41 -173.5(3) . . . . ? F42 C40 S40 O41 68.1(4) . . . . ? F40 C40 S40 O42 67.3(4) . . . . ? F41 C40 S40 O42 -53.8(4) . . . . ? F42 C40 S40 O42 -172.3(4) . . . . ? F51 C50 S50 O50 171.5(8) . . . . ? F50 C50 S50 O50 -56.2(8) . . . . ? F52 C50 S50 O50 63.3(6) . . . . ? F51 C50 S50 O51 -77.4(8) . . . . ? F50 C50 S50 O51 55.0(8) . . . . ? F52 C50 S50 O51 174.4(6) . . . . ? F51 C50 S50 O52 43.8(9) . . . . ? F50 C50 S50 O52 176.1(6) . . . . ? F52 C50 S50 O52 -64.4(6) . . . . ? O65 S60 C60 F61 19.5(10) . . . . ? O60 S60 C60 F61 -65.5(9) . . . . ? O61 S60 C60 F61 164.0(8) . . . . ? O64 S60 C60 F61 142.2(9) . . . . ? O62 S60 C60 F61 49.0(9) . . . . ? O63 S60 C60 F61 -104.8(9) . . . . ? C61 S60 C60 F61 -88.9(13) . . . . ? O65 S60 C60 F60 -97.9(9) . . . . ? O60 S60 C60 F60 177.1(7) . . . . ? O61 S60 C60 F60 46.6(8) . . . . ? O64 S60 C60 F60 24.9(8) . . . . ? O62 S60 C60 F60 -68.4(8) . . . . ? O63 S60 C60 F60 137.8(7) . . . . ? C61 S60 C60 F60 153.7(16) . . . . ? O65 S60 C60 F62 142.3(8) . . . . ? O60 S60 C60 F62 57.3(7) . . . . ? O61 S60 C60 F62 -73.2(7) . . . . ? O64 S60 C60 F62 -94.9(7) . . . . ? O62 S60 C60 F62 171.8(6) . . . . ? O63 S60 C60 F62 18.0(8) . . . . ? C61 S60 C60 F62 33.9(11) . . . . ? O65 S60 C61 F65 57.7(10) . . . . ? O60 S60 C61 F65 -25.6(9) . . . . ? O61 S60 C61 F65 -147.8(9) . . . . ? O64 S60 C61 F65 -176.6(9) . . . . ? O62 S60 C61 F65 82.2(10) . . . . ? O63 S60 C61 F65 -61.5(10) . . . . ? C60 S60 C61 F65 131.7(17) . . . . ? O65 S60 C61 F64 -68.4(11) . . . . ? O60 S60 C61 F64 -151.7(10) . . . . ? O61 S60 C61 F64 86.1(10) . . . . ? O64 S60 C61 F64 57.3(10) . . . . ? O62 S60 C61 F64 -43.9(11) . . . . ? O63 S60 C61 F64 172.4(10) . . . . ? C60 S60 C61 F64 5.6(10) . . . . ? O65 S60 C61 F63 177.2(9) . . . . ? O60 S60 C61 F63 93.9(9) . . . . ? O61 S60 C61 F63 -28.3(9) . . . . ? O64 S60 C61 F63 -57.1(9) . . . . ? O62 S60 C61 F63 -158.3(8) . . . . ? O63 S60 C61 F63 58.0(9) . . . . ? C60 S60 C61 F63 -108.8(14) . . . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.922 _refine_diff_density_max 1.220 _refine_diff_density_min -0.916 _refine_diff_density_rms 0.082 # Attachment 'web_deposit_cif_file_8_BernhardSpingler_1312475891.5.cif' data_am250306 _database_code_depnum_ccdc_archive 'CCDC 661099' #TrackingRef 'web_deposit_cif_file_8_BernhardSpingler_1312475891.5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H24 I N3' _chemical_formula_weight 337.24 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 16.6238(5) _cell_length_b 9.1011(5) _cell_length_c 9.5117(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1439.07(18) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 2.207 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6091 _exptl_absorpt_correction_T_max 0.7451 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '/f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 13 _diffrn_standards_decay_% ? _diffrn_reflns_number 26656 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 30.51 _reflns_number_total 2295 _reflns_number_gt 2048 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _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^)+(0.0721P)^2^+1.1926P] 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 SHELXL _refine_ls_extinction_coef 0.040(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2295 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1340 _refine_ls_wR_factor_gt 0.1262 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.159 _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 I1 I 0.152346(17) 0.2500 0.20776(3) 0.04639(19) Uani 1 2 d S . . N2 N 0.18187(16) 0.1216(3) 0.7513(3) 0.0436(5) Uani 1 1 d . . . N1 N 0.0163(2) 0.2500 0.7370(4) 0.0411(7) Uani 1 2 d S . . C8 C 0.1681(3) 0.2500 0.8084(5) 0.0439(9) Uani 1 2 d S . . H8A H 0.1463 0.2500 0.8985 0.053 Uiso 1 2 calc SR . . C5 C 0.1401(2) -0.0059(5) 0.8116(4) 0.0523(8) Uani 1 1 d . . . H5A H 0.1430 -0.0005 0.9133 0.063 Uiso 1 1 calc R . . H5B H 0.1675 -0.0949 0.7823 0.063 Uiso 1 1 calc R . . C2 C -0.0181(3) 0.2500 0.5947(5) 0.0483(9) Uani 1 2 d S . . H2A H 0.0021 0.1642 0.5456 0.058 Uiso 0.50 1 calc PR . . H2B H 0.0021 0.3358 0.5456 0.058 Uiso 0.50 1 calc PR . . C3 C -0.0002(2) 0.1138(4) 0.8166(4) 0.0474(7) Uani 1 1 d . . . H3B H -0.0564 0.0878 0.8058 0.057 Uiso 1 1 calc R . . H3A H 0.0097 0.1314 0.9157 0.057 Uiso 1 1 calc R . . C7 C 0.2579(3) 0.2500 0.5695(5) 0.0490(10) Uani 1 2 d S . . H7A H 0.3079 0.2500 0.6219 0.059 Uiso 1 2 calc SR . . H7B H 0.2709 0.2500 0.4700 0.059 Uiso 1 2 calc SR . . C4 C 0.0521(2) -0.0150(4) 0.7674(4) 0.0506(7) Uani 1 1 d . . . H4A H 0.0295 -0.1054 0.8042 0.061 Uiso 1 1 calc R . . H4B H 0.0496 -0.0203 0.6657 0.061 Uiso 1 1 calc R . . C6 C 0.2101(2) 0.1132(4) 0.6050(3) 0.0472(6) Uani 1 1 d . . . H6A H 0.1644 0.1047 0.5421 0.057 Uiso 1 1 calc R . . H6B H 0.2436 0.0268 0.5930 0.057 Uiso 1 1 calc R . . C1 C -0.1102(3) 0.2500 0.5832(6) 0.0643(14) Uani 1 2 d S . . H1C H -0.1311 0.3384 0.6243 0.077 Uiso 0.50 1 calc PR . . H1B H -0.1315 0.1663 0.6321 0.077 Uiso 0.50 1 calc PR . . H1A H -0.1255 0.2453 0.4860 0.077 Uiso 0.50 1 calc PR . . 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 I1 0.0446(2) 0.0515(3) 0.0430(2) 0.000 -0.00229(9) 0.000 N2 0.0422(12) 0.0475(13) 0.0412(12) 0.0061(11) 0.0021(10) 0.0029(11) N1 0.0416(17) 0.0401(16) 0.0417(16) 0.000 0.0014(14) 0.000 C8 0.0398(19) 0.052(3) 0.039(2) 0.000 -0.0035(16) 0.000 C5 0.0567(18) 0.0452(17) 0.0550(18) 0.0107(15) 0.0077(14) 0.0077(15) C2 0.046(2) 0.055(2) 0.044(2) 0.000 -0.0045(17) 0.000 C3 0.0435(15) 0.0474(15) 0.0513(15) 0.0037(13) 0.0047(12) -0.0013(13) C7 0.044(2) 0.061(3) 0.042(2) 0.000 0.0049(16) 0.000 C4 0.0552(18) 0.0407(14) 0.0560(17) 0.0015(13) 0.0048(14) -0.0031(13) C6 0.0496(15) 0.0487(15) 0.0434(14) 0.0005(12) 0.0060(12) 0.0074(13) C1 0.049(2) 0.085(4) 0.059(3) 0.000 -0.008(2) 0.000 _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 N2 C8 1.309(4) . ? N2 C5 1.469(5) . ? N2 C6 1.470(4) . ? N1 C2 1.469(6) . ? N1 C3 1.478(4) 8_565 ? N1 C3 1.478(4) . ? C8 N2 1.309(4) 8_565 ? C8 H8A 0.9300 . ? C5 C4 1.524(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C2 C1 1.535(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.532(5) . ? C3 H3B 0.9700 . ? C3 H3A 0.9700 . ? C7 C6 1.516(4) 8_565 ? C7 C6 1.516(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C1 H1C 0.9600 . ? C1 H1B 0.9600 . ? C1 H1A 0.9600 . ? 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 C8 N2 C5 117.4(3) . . ? C8 N2 C6 119.7(3) . . ? C5 N2 C6 118.6(3) . . ? C2 N1 C3 113.6(2) . 8_565 ? C2 N1 C3 113.6(2) . . ? C3 N1 C3 114.0(4) 8_565 . ? N2 C8 N2 126.4(4) . 8_565 ? N2 C8 H8A 116.8 . . ? N2 C8 H8A 116.8 8_565 . ? N2 C5 C4 112.9(3) . . ? N2 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? N2 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? N1 C2 C1 117.0(4) . . ? N1 C2 H2A 108.1 . . ? C1 C2 H2A 108.1 . . ? N1 C2 H2B 108.1 . . ? C1 C2 H2B 108.1 . . ? H2A C2 H2B 107.3 . . ? N1 C3 C4 112.4(3) . . ? N1 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? N1 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? H3B C3 H3A 107.9 . . ? C6 C7 C6 110.5(4) 8_565 . ? C6 C7 H7A 109.5 8_565 . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 8_565 . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C5 C4 C3 114.7(3) . . ? C5 C4 H4A 108.6 . . ? C3 C4 H4A 108.6 . . ? C5 C4 H4B 108.6 . . ? C3 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? N2 C6 C7 109.6(3) . . ? N2 C6 H6A 109.7 . . ? C7 C6 H6A 109.7 . . ? N2 C6 H6B 109.7 . . ? C7 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? C2 C1 H1C 109.5 . . ? C2 C1 H1B 109.5 . . ? H1C C1 H1B 109.5 . . ? C2 C1 H1A 109.5 . . ? H1C C1 H1A 109.5 . . ? H1B C1 H1A 109.5 . . ? 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 C5 N2 C8 N2 -161.4(4) . . . 8_565 ? C6 N2 C8 N2 -4.9(7) . . . 8_565 ? C8 N2 C5 C4 77.0(4) . . . . ? C6 N2 C5 C4 -79.8(4) . . . . ? C3 N1 C2 C1 -66.2(3) 8_565 . . . ? C3 N1 C2 C1 66.2(3) . . . . ? C2 N1 C3 C4 75.4(4) . . . . ? C3 N1 C3 C4 -152.3(3) 8_565 . . . ? N2 C5 C4 C3 -63.0(4) . . . . ? N1 C3 C4 C5 73.3(4) . . . . ? C8 N2 C6 C7 29.0(5) . . . . ? C5 N2 C6 C7 -174.8(3) . . . . ? C6 C7 C6 N2 -52.3(5) 8_565 . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.355 _refine_diff_density_min -0.868 _refine_diff_density_rms 0.116