# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry, 1999 # CCDC Number: 182/1322 #---------------------------------------------------------- #1 Data block identification data_global #---------------------------------------------------------- #2 Person making the deposition _publ_contact_author ; M.C. Ramirez de Arellano Deparatmento de Quimica Organica Facultad de Quimica Universidad de Valencia 46100 Valencia Spain ; _publ_contact_author_phone '610 413 143' _publ_contact_author_fax '038 963 864 939' _publ_contact_author_email mcra@uv.es #---------------------------------------------------------- #3 Publication details _publ_name 'J. Chem. Soc., Chemical Communications' _publ_author_names 'J. Vicente, M.T. Chicote, R. Guerrero and M.C. Ramirez de Arellano' _publ_section_title ; The first complex with acetonine as ligand. The first crystal structure of an acetonine derivative ; #------------------------------------------------------------ data_rgs01 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H36 Au Cl N4 O4' _chemical_formula_weight 604.92 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Au' 'Au' -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.871(2) _cell_length_b 14.707(2) _cell_length_c 11.8412(15) _cell_angle_alpha 90.00 _cell_angle_beta 123.910(6) _cell_angle_gamma 90.00 _cell_volume 2293.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 12.005 _cell_measurement_theta_max 12.442 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.752 _exptl_crystal_density_method ? _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 6.560 _exptl_absorpt_correction_type psi-scans _exptl_absorpt_correction_T_min 0.140 _exptl_absorpt_correction_T_max 0.732 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 Siemens-P4 _diffrn_measurement_method w\scans _diffrn_standards_number 3 _diffrn_standards_interval_count 247 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.20 _diffrn_reflns_number 3514 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2009 _reflns_number_observed 1514 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 4 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses of fit S are based on F^2^, conventional R- factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The perclorate anion is disordered over two sites. A large peak of 1.4 e\%A^3^ was observed at 1.10 \%A from the gold atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+4.8418P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary Patterson _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'free NH, rigid methyls, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2005 _refine_ls_number_parameters 133 _refine_ls_number_restraints 131 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_obs 0.0287 _refine_ls_wR_factor_all 0.0811 _refine_ls_wR_factor_obs 0.0709 _refine_ls_goodness_of_fit_all 1.097 _refine_ls_goodness_of_fit_obs 1.166 _refine_ls_restrained_S_all 1.146 _refine_ls_restrained_S_obs 1.163 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Au Au 0.0000 0.0000 0.0000 0.03002(13) Uani 1 d S . N1 N 0.1384(4) 0.0297(3) 0.1716(5) 0.0294(9) Uani 1 d U . N2 N 0.2694(3) 0.1472(3) 0.3134(4) 0.0302(9) Uani 1 d DU . H2 H 0.3146(37) 0.1452(40) 0.2953(60) 0.036 Uiso 1 d D . C1 C 0.1967(5) -0.0326(4) 0.2576(6) 0.0321(12) Uani 1 d U . C2 C 0.2990(5) -0.0108(4) 0.3833(6) 0.0358(12) Uani 1 d U . H2A H 0.3518(5) -0.0210(4) 0.3646(6) 0.043 Uiso 1 calc R . H2B H 0.3128(5) -0.0528(4) 0.4572(6) 0.043 Uiso 1 calc R . C3 C 0.3062(4) 0.0871(4) 0.4311(6) 0.0328(12) Uani 1 d U . C4 C 0.1690(4) 0.1285(4) 0.1886(6) 0.0303(11) Uani 1 d U . C5 C 0.1649(5) -0.1295(4) 0.2346(6) 0.0402(14) Uani 1 d U . H5A H 0.1542(28) -0.1495(8) 0.3047(23) 0.048 Uiso 1 calc R . H5B H 0.2179(13) -0.1669(5) 0.2392(37) 0.048 Uiso 1 calc R . H5C H 0.1015(15) -0.1362(6) 0.1446(17) 0.048 Uiso 1 calc R . C6 C 0.4155(5) 0.1128(5) 0.5368(6) 0.0436(15) Uani 1 d U . H6A H 0.4432(10) 0.0721(17) 0.6154(18) 0.052 Uiso 1 calc R . H6B H 0.4184(5) 0.1757(9) 0.5660(28) 0.052 Uiso 1 calc R . H6C H 0.4556(8) 0.1071(25) 0.4974(13) 0.052 Uiso 1 calc R . C7 C 0.2457(5) 0.0975(4) 0.4952(6) 0.0410(14) Uani 1 d U . H7A H 0.2802(16) 0.0648(22) 0.5821(20) 0.049 Uiso 1 calc R . H7B H 0.1775(11) 0.0723(24) 0.4338(18) 0.049 Uiso 1 calc R . H7C H 0.2406(26) 0.1621(5) 0.5109(37) 0.049 Uiso 1 calc R . C8 C 0.0877(4) 0.1842(4) 0.1862(7) 0.0426(14) Uani 1 d U . H8A H 0.1064(15) 0.2487(5) 0.1981(39) 0.051 Uiso 1 calc R . H8B H 0.0814(20) 0.1644(18) 0.2602(24) 0.051 Uiso 1 calc R . H8C H 0.0226(7) 0.1756(20) 0.0988(16) 0.051 Uiso 1 calc R . C9 C 0.1743(5) 0.1523(4) 0.0677(6) 0.0396(13) Uani 1 d U . H9A H 0.1982(29) 0.2151(10) 0.0769(21) 0.047 Uiso 1 calc R . H9B H 0.1067(7) 0.1464(26) -0.0166(7) 0.047 Uiso 1 calc R . H9C H 0.2215(23) 0.1109(17) 0.0648(23) 0.047 Uiso 1 calc R . Cl Cl 0.5000 0.1390(2) 0.2500 0.0418(5) Uani 1 d SDU . O1 O 0.4551(10) 0.1813(11) 0.1156(16) 0.0684(14) Uiso 0.61(3) d PDU 1 O2 O 0.4293(10) 0.0749(9) 0.2424(15) 0.0684(14) Uiso 0.61(3) d PDU 1 O1' O 0.4718(15) 0.2063(14) 0.1577(26) 0.0684(14) Uiso 0.39(3) d PDU 2 O2' O 0.4116(14) 0.0906(13) 0.2216(21) 0.0684(14) Uiso 0.39(3) d PDU 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 Au 0.0253(2) 0.0262(2) 0.0293(2) -0.00136(13) 0.00952(14) 0.00070(13) N1 0.025(2) 0.029(2) 0.026(2) -0.001(2) 0.009(2) 0.000(2) N2 0.022(2) 0.032(2) 0.029(2) 0.001(2) 0.009(2) -0.003(2) C1 0.031(3) 0.032(3) 0.031(3) -0.001(2) 0.016(3) 0.002(2) C2 0.035(3) 0.032(3) 0.030(3) 0.007(2) 0.012(2) 0.005(2) C3 0.027(3) 0.036(3) 0.031(3) 0.001(2) 0.013(2) -0.004(2) C4 0.024(3) 0.025(3) 0.034(3) 0.002(2) 0.011(2) 0.003(2) C5 0.041(4) 0.029(3) 0.035(3) 0.004(3) 0.012(3) 0.006(3) C6 0.035(3) 0.050(4) 0.030(3) 0.003(3) 0.008(3) -0.008(3) C7 0.048(4) 0.040(3) 0.043(3) -0.007(3) 0.030(3) -0.007(3) C8 0.029(3) 0.033(3) 0.050(4) -0.005(3) 0.012(3) 0.006(3) C9 0.036(3) 0.037(3) 0.031(3) 0.006(3) 0.009(3) -0.001(3) Cl 0.0360(12) 0.0444(12) 0.0380(10) 0.000 0.0163(9) 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. Possible H bonds: Distance X..Y 3.265 (0.014) N2 - O2 3.115 (0.019) N2 - O2' Distance H..Y 2.460 (0.037) H2 - O2 2.297 (0.038) H2 - O2' Angle XHY 157.05 ( 5.29) N2 - H2 - O2 160.07 ( 5.43) N2 - H2 - O2' ; 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 Au N1 2.040(5) . ? Au N1 2.041(5) 5 ? N1 C1 1.297(8) . ? N1 C4 1.510(7) . ? N2 C4 1.474(7) . ? N2 C3 1.469(7) . ? C1 C5 1.487(8) . ? C1 C2 1.502(8) . ? C2 C3 1.528(7) . ? C3 C6 1.515(8) . ? C3 C7 1.529(7) . ? C4 C8 1.517(7) . ? C4 C9 1.521(7) . ? Cl O1' 1.352(12) 2_655 ? Cl O1' 1.352(12) . ? Cl O2 1.430(9) . ? Cl O2 1.430(9) 2_655 ? Cl O2' 1.435(13) . ? Cl O2' 1.435(13) 2_655 ? Cl O1 1.470(10) . ? Cl O1 1.470(10) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Au N1 180.0 . 5 ? C1 N1 C4 122.6(5) . . ? C1 N1 Au 122.1(4) . . ? C4 N1 Au 115.2(3) . . ? C4 N2 C3 118.3(4) . . ? N1 C1 C5 120.8(6) . . ? N1 C1 C2 122.1(5) . . ? C5 C1 C2 117.0(5) . . ? C1 C2 C3 112.6(5) . . ? N2 C3 C6 107.4(4) . . ? N2 C3 C2 108.0(4) . . ? C6 C3 C2 110.9(5) . . ? N2 C3 C7 112.5(5) . . ? C6 C3 C7 108.1(5) . . ? C2 C3 C7 109.9(5) . . ? N2 C4 N1 113.6(4) . . ? N2 C4 C8 110.5(5) . . ? N1 C4 C8 108.0(4) . . ? N2 C4 C9 107.7(4) . . ? N1 C4 C9 106.3(4) . . ? C8 C4 C9 110.6(5) . . ? O1' Cl O1' 85.9(26) 2_655 . ? O2 Cl O2 97.4(12) . 2_655 ? O1' Cl O2' 113.1(11) 2_655 . ? O1' Cl O2' 109.5(8) . . ? O1' Cl O2' 109.5(8) 2_655 2_655 ? O1' Cl O2' 113.1(11) . 2_655 ? O2' Cl O2' 120.5(18) . 2_655 ? O2 Cl O1 108.8(6) . . ? O2 Cl O1 103.7(8) 2_655 . ? O2 Cl O1 103.7(8) . 2_655 ? O2 Cl O1 108.8(6) 2_655 2_655 ? O1 Cl O1 130.0(16) . 2_655 ? _refine_diff_density_max 1.405 _refine_diff_density_min -0.660 _refine_diff_density_rms 0.124 #======END