# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Dietrich Gudat' _publ_contact_author_address ; Institut fur Anorganische Chemie Universitat Stuttgart Pfaffenwaldring 55 Stuttgart 70550 GERMANY ; _publ_contact_author_email GUDAT@IAC.UNI-STUTTGART.DE _publ_section_title ; Synthesis and Unprecedented Oxidation of a Cationic Sb-Analogue of an Arduengo's Carbene ; loop_ _publ_author_name 'Dietrich Gudat' 'Timo Gans-Eichler' 'Martin Nieger' data_gudat53m _database_code_depnum_ccdc_archive 'CCDC 242440' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-Di-tert.butyl-2-chloro-1,3,2-diazastibolene ; _chemical_name_common 1,3-Di-tert.butyl-2-chloro-1,3,2-diazastibolene _chemical_melting_point ? _chemical_formula_moiety 'C10 H20 Cl N2 Sb' _chemical_formula_sum 'C10 H20 Cl N2 Sb' _chemical_formula_weight 325.48 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.5242(5) _cell_length_b 10.9946(4) _cell_length_c 21.0980(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2673.20(19) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3265 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plates _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 2.234 _exptl_absorpt_correction_type 'empirical from multiple refl.' _exptl_absorpt_correction_T_min 0.3830 _exptl_absorpt_correction_T_max 0.5204 _exptl_absorpt_process_details 'MULABS (Platon, cf. Blessing, 1995)' _exptl_special_details ; dx = 40 mm, 240 sec./deg. 0.5 deg., 3 sets, 591 frames, mos.= 1.151(2) deg. ; _diffrn_ambient_temperature 123(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 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 0.5 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 13862 _diffrn_reflns_av_R_equivalents 0.1043 _diffrn_reflns_av_sigmaI/netI 0.0667 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2344 _reflns_number_gt 1596 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _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^)+(0.0445P)^2^+0.0000P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2344 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_restrained_S_all 0.933 _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 Cl1 Cl 0.59992(12) 0.39170(13) 0.14862(6) 0.0397(4) Uani 1 1 d . . . Sb1 Sb 0.73632(3) 0.58526(3) 0.150652(15) 0.02766(15) Uani 1 1 d . . . N1 N 0.6792(3) 0.6666(4) 0.22939(18) 0.0252(10) Uani 1 1 d . . . N2 N 0.6287(3) 0.7055(4) 0.11053(19) 0.0280(10) Uani 1 1 d . . . C1 C 0.5907(4) 0.7516(5) 0.2171(2) 0.0280(12) Uani 1 1 d . . . H1 H 0.5504 0.7923 0.2502 0.034 Uiso 1 1 calc R . . C2 C 0.5669(4) 0.7715(5) 0.1555(2) 0.0266(12) Uani 1 1 d . . . H2 H 0.5096 0.8289 0.1432 0.032 Uiso 1 1 calc R . . C11 C 0.7040(4) 0.6257(5) 0.2949(2) 0.0256(12) Uani 1 1 d . . . C12 C 0.7250(4) 0.7363(5) 0.3376(2) 0.0324(13) Uani 1 1 d . . . H12A H 0.6546 0.7862 0.3392 0.049 Uiso 1 1 calc R . . H12B H 0.7891 0.7848 0.3205 0.049 Uiso 1 1 calc R . . H12C H 0.7448 0.7088 0.3805 0.049 Uiso 1 1 calc R . . C13 C 0.6016(4) 0.5513(5) 0.3198(2) 0.0349(14) Uani 1 1 d . . . H13A H 0.5318 0.6022 0.3207 0.052 Uiso 1 1 calc R . . H13B H 0.6188 0.5226 0.3628 0.052 Uiso 1 1 calc R . . H13C H 0.5884 0.4812 0.2920 0.052 Uiso 1 1 calc R . . C14 C 0.8146(4) 0.5488(5) 0.2932(2) 0.0319(13) Uani 1 1 d . . . H14A H 0.8790 0.5982 0.2770 0.048 Uiso 1 1 calc R . . H14B H 0.8028 0.4786 0.2653 0.048 Uiso 1 1 calc R . . H14C H 0.8330 0.5204 0.3360 0.048 Uiso 1 1 calc R . . C21 C 0.5988(4) 0.7149(5) 0.0426(2) 0.0301(12) Uani 1 1 d . . . C22 C 0.6783(5) 0.6295(5) 0.0061(3) 0.0377(14) Uani 1 1 d . . . H22A H 0.7592 0.6540 0.0125 0.057 Uiso 1 1 calc R . . H22B H 0.6595 0.6334 -0.0392 0.057 Uiso 1 1 calc R . . H22C H 0.6675 0.5461 0.0214 0.057 Uiso 1 1 calc R . . C23 C 0.4728(5) 0.6758(6) 0.0325(3) 0.0438(16) Uani 1 1 d . . . H23A H 0.4212 0.7305 0.0560 0.066 Uiso 1 1 calc R . . H23B H 0.4625 0.5924 0.0478 0.066 Uiso 1 1 calc R . . H23C H 0.4541 0.6795 -0.0128 0.066 Uiso 1 1 calc R . . C24 C 0.6185(6) 0.8457(5) 0.0201(3) 0.0472(17) Uani 1 1 d . . . H24A H 0.6997 0.8683 0.0271 0.071 Uiso 1 1 calc R . . H24B H 0.5680 0.9008 0.0440 0.071 Uiso 1 1 calc R . . H24C H 0.6004 0.8517 -0.0252 0.071 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 Cl1 0.0363(8) 0.0370(9) 0.0458(9) -0.0021(7) 0.0021(6) -0.0037(6) Sb1 0.0204(2) 0.0304(2) 0.0322(2) -0.00188(18) 0.00133(14) 0.00223(15) N1 0.022(2) 0.024(3) 0.030(3) 0.001(2) -0.0045(18) -0.0004(18) N2 0.027(2) 0.028(3) 0.029(3) -0.003(2) -0.0021(18) 0.005(2) C1 0.025(3) 0.027(3) 0.032(3) -0.004(3) 0.000(2) 0.000(2) C2 0.022(3) 0.019(3) 0.039(3) -0.002(3) 0.001(2) 0.004(2) C11 0.023(3) 0.025(3) 0.029(3) 0.004(2) -0.001(2) -0.002(2) C12 0.029(3) 0.030(3) 0.038(3) -0.002(3) -0.007(2) 0.001(2) C13 0.031(3) 0.038(4) 0.036(3) 0.001(3) 0.005(2) -0.006(3) C14 0.030(3) 0.032(3) 0.033(3) 0.004(3) -0.003(2) 0.003(2) C21 0.032(3) 0.027(3) 0.031(3) -0.001(3) 0.004(2) 0.004(2) C22 0.037(3) 0.038(4) 0.038(3) 0.001(3) 0.004(3) 0.002(3) C23 0.035(3) 0.062(5) 0.035(4) -0.009(3) -0.005(3) 0.000(3) C24 0.068(5) 0.040(4) 0.034(4) 0.008(3) 0.002(3) 0.003(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 Cl1 Sb1 2.6460(15) . ? Sb1 N1 1.998(4) . ? Sb1 N2 2.000(4) . ? Sb1 Cl1 3.8620(15) 8_765 ? N1 C1 1.407(6) . ? N1 C11 1.481(6) . ? N2 C2 1.391(6) . ? N2 C21 1.478(6) . ? C1 C2 1.346(6) . ? C1 H1 0.9500 . ? C2 H2 0.9500 . ? C11 C13 1.530(7) . ? C11 C14 1.531(7) . ? C11 C12 1.533(7) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C21 C22 1.522(7) . ? C21 C23 1.528(7) . ? C21 C24 1.531(7) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 Sb1 N2 81.49(16) . . ? N1 Sb1 Cl1 100.23(12) . . ? N2 Sb1 Cl1 99.00(12) . . ? N1 Sb1 Cl1 77.28(12) . 8_765 ? N2 Sb1 Cl1 73.84(12) . 8_765 ? Cl1 Sb1 Cl1 172.64(3) . 8_765 ? C1 N1 C11 120.9(4) . . ? C1 N1 Sb1 112.5(3) . . ? C11 N1 Sb1 125.2(3) . . ? C2 N2 C21 120.4(4) . . ? C2 N2 Sb1 111.9(3) . . ? C21 N2 Sb1 127.0(3) . . ? C2 C1 N1 115.7(4) . . ? C2 C1 H1 122.2 . . ? N1 C1 H1 122.2 . . ? C1 C2 N2 118.0(4) . . ? C1 C2 H2 121.0 . . ? N2 C2 H2 121.0 . . ? N1 C11 C13 109.5(4) . . ? N1 C11 C14 107.8(4) . . ? C13 C11 C14 110.8(5) . . ? N1 C11 C12 109.8(4) . . ? C13 C11 C12 110.1(4) . . ? C14 C11 C12 108.7(4) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C21 C22 107.8(4) . . ? N2 C21 C23 109.7(4) . . ? C22 C21 C23 109.1(5) . . ? N2 C21 C24 109.4(4) . . ? C22 C21 C24 109.5(4) . . ? C23 C21 C24 111.2(5) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 N2 Sb1 N1 C1 5.6(3) . . . . ? Cl1 Sb1 N1 C1 -92.1(3) . . . . ? Cl1 Sb1 N1 C1 80.8(3) 8_765 . . . ? N2 Sb1 N1 C11 172.0(4) . . . . ? Cl1 Sb1 N1 C11 74.4(4) . . . . ? Cl1 Sb1 N1 C11 -112.7(4) 8_765 . . . ? N1 Sb1 N2 C2 -4.8(3) . . . . ? Cl1 Sb1 N2 C2 94.3(3) . . . . ? Cl1 Sb1 N2 C2 -84.0(3) 8_765 . . . ? N1 Sb1 N2 C21 -175.0(4) . . . . ? Cl1 Sb1 N2 C21 -75.9(4) . . . . ? Cl1 Sb1 N2 C21 105.8(4) 8_765 . . . ? C11 N1 C1 C2 -172.6(4) . . . . ? Sb1 N1 C1 C2 -5.5(5) . . . . ? N1 C1 C2 N2 1.5(7) . . . . ? C21 N2 C2 C1 174.2(4) . . . . ? Sb1 N2 C2 C1 3.3(6) . . . . ? C1 N1 C11 C13 67.3(6) . . . . ? Sb1 N1 C11 C13 -98.1(5) . . . . ? C1 N1 C11 C14 -172.0(4) . . . . ? Sb1 N1 C11 C14 22.6(6) . . . . ? C1 N1 C11 C12 -53.7(6) . . . . ? Sb1 N1 C11 C12 140.9(3) . . . . ? C2 N2 C21 C22 -178.1(4) . . . . ? Sb1 N2 C21 C22 -8.6(6) . . . . ? C2 N2 C21 C23 -59.3(6) . . . . ? Sb1 N2 C21 C23 110.1(4) . . . . ? C2 N2 C21 C24 62.9(6) . . . . ? Sb1 N2 C21 C24 -127.6(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 Cl1 0.95 2.96 3.902(5) 171.9 3_655 C23 H23C Cl1 0.98 3.04 3.982(6) 162.7 5_665 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.123 _refine_diff_density_min -0.970 _refine_diff_density_rms 0.129 #============================================================================== data_gudat62m _database_code_depnum_ccdc_archive 'CCDC 242441' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-Di-tert.butyl-2-chloro-1,3,2-diazastibolenium tetrachloroantmonate ; _chemical_name_common ;1,3-Di-tert.butyl-2-chloro-1,3,2-diazastibolenium tetrachloroantmonate ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H20 Cl4 N2 Sb2' _chemical_formula_sum 'C10 H20 Cl4 N2 Sb2' _chemical_formula_weight 553.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1078(1) _cell_length_b 19.5200(2) _cell_length_c 10.2340(1) _cell_angle_alpha 90.00 _cell_angle_beta 114.408(1) _cell_angle_gamma 90.00 _cell_volume 1838.75(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4177 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.000 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 3.506 _exptl_absorpt_correction_type 'empirical from multiple refl.' _exptl_absorpt_correction_T_min 0.2458 _exptl_absorpt_correction_T_max 0.3297 _exptl_absorpt_process_details 'MULABS (Platon, cf. Blessing, 1995)' _exptl_special_details ; dx = 40 mm, 40 sec./deg., 1 deg., 4 sets, 468 frames, mos.= 0.542(1) deg. ; _diffrn_ambient_temperature 123(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 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 16986 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3213 _reflns_number_gt 3115 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _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^)+(0.0065P)^2^+1.9532P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3213 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0192 _refine_ls_R_factor_gt 0.0180 _refine_ls_wR_factor_ref 0.0419 _refine_ls_wR_factor_gt 0.0416 _refine_ls_goodness_of_fit_ref 1.214 _refine_ls_restrained_S_all 1.214 _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 Sb1 Sb 0.830392(19) 0.097096(9) 0.341584(19) 0.01735(6) Uani 1 1 d . . . N1 N 0.8318(2) 0.19929(11) 0.3762(2) 0.0162(4) Uani 1 1 d . . . C1 C 0.8289(3) 0.23692(14) 0.2637(3) 0.0216(6) Uani 1 1 d . . . H1 H 0.8319 0.2856 0.2671 0.026 Uiso 1 1 calc R . . C2 C 0.8214(3) 0.20205(14) 0.1458(3) 0.0213(6) Uani 1 1 d . . . H2 H 0.8201 0.2252 0.0637 0.026 Uiso 1 1 calc R . . N2 N 0.8159(2) 0.13287(11) 0.1506(2) 0.0167(5) Uani 1 1 d . . . C11 C 0.8215(3) 0.23284(14) 0.5034(3) 0.0182(5) Uani 1 1 d . . . C12 C 0.8438(3) 0.17866(15) 0.6171(3) 0.0261(6) Uani 1 1 d . . . H12A H 0.9415 0.1592 0.6487 0.039 Uiso 1 1 calc R . . H12B H 0.7714 0.1423 0.5768 0.039 Uiso 1 1 calc R . . H12C H 0.8329 0.1995 0.6992 0.039 Uiso 1 1 calc R . . C13 C 0.9371(4) 0.28840(17) 0.5621(3) 0.0351(7) Uani 1 1 d . . . H13A H 0.9211 0.3231 0.4879 0.053 Uiso 1 1 calc R . . H13B H 1.0335 0.2679 0.5900 0.053 Uiso 1 1 calc R . . H13C H 0.9310 0.3098 0.6460 0.053 Uiso 1 1 calc R . . C14 C 0.6698(3) 0.26388(19) 0.4548(3) 0.0369(8) Uani 1 1 d . . . H14A H 0.6557 0.2987 0.3813 0.055 Uiso 1 1 calc R . . H14B H 0.6598 0.2850 0.5371 0.055 Uiso 1 1 calc R . . H14C H 0.5967 0.2278 0.4149 0.055 Uiso 1 1 calc R . . C21 C 0.7997(3) 0.09076(14) 0.0227(3) 0.0201(6) Uani 1 1 d . . . C22 C 0.7833(3) 0.01590(15) 0.0571(3) 0.0245(6) Uani 1 1 d . . . H22A H 0.8707 0.0012 0.1397 0.037 Uiso 1 1 calc R . . H22B H 0.7700 -0.0127 -0.0261 0.037 Uiso 1 1 calc R . . H22C H 0.6985 0.0112 0.0798 0.037 Uiso 1 1 calc R . . C23 C 0.9354(3) 0.10044(16) -0.0051(3) 0.0260(6) Uani 1 1 d . . . H23A H 1.0207 0.0849 0.0787 0.039 Uiso 1 1 calc R . . H23B H 0.9464 0.1490 -0.0225 0.039 Uiso 1 1 calc R . . H23C H 0.9263 0.0736 -0.0893 0.039 Uiso 1 1 calc R . . C24 C 0.6637(3) 0.11316(16) -0.1067(3) 0.0273(6) Uani 1 1 d . . . H24A H 0.6740 0.1611 -0.1294 0.041 Uiso 1 1 calc R . . H24B H 0.5787 0.1084 -0.0845 0.041 Uiso 1 1 calc R . . H24C H 0.6511 0.0843 -0.1894 0.041 Uiso 1 1 calc R . . Sb2 Sb 0.356744(18) 0.078880(9) 0.503638(18) 0.01707(6) Uani 1 1 d . . . Cl1 Cl 0.50059(7) 0.05228(4) 0.33816(8) 0.02823(16) Uani 1 1 d . . . Cl2 Cl 0.20746(8) 0.09073(4) 0.64756(8) 0.02711(16) Uani 1 1 d . . . Cl3 Cl 0.23623(8) 0.17527(3) 0.35239(7) 0.02876(16) Uani 1 1 d . . . Cl4 Cl 0.17892(7) 0.00207(3) 0.35206(7) 0.02129(14) 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 Sb1 0.02468(10) 0.01348(10) 0.01702(10) 0.00020(7) 0.01176(8) 0.00004(7) N1 0.0185(11) 0.0135(11) 0.0158(11) -0.0013(9) 0.0064(9) -0.0001(8) C1 0.0279(14) 0.0154(13) 0.0184(14) 0.0028(11) 0.0065(12) -0.0004(11) C2 0.0277(14) 0.0180(14) 0.0186(14) 0.0035(11) 0.0098(12) -0.0008(11) N2 0.0176(10) 0.0195(12) 0.0128(11) -0.0010(9) 0.0058(9) -0.0016(9) C11 0.0196(13) 0.0170(13) 0.0157(13) -0.0032(11) 0.0051(11) 0.0029(10) C12 0.0351(16) 0.0243(15) 0.0208(15) -0.0013(12) 0.0134(13) 0.0016(12) C13 0.0476(19) 0.0331(18) 0.0221(16) -0.0105(14) 0.0121(15) -0.0184(15) C14 0.0292(16) 0.053(2) 0.0240(16) -0.0040(15) 0.0062(13) 0.0205(15) C21 0.0242(14) 0.0227(14) 0.0142(14) -0.0044(11) 0.0088(12) -0.0018(11) C22 0.0301(15) 0.0231(15) 0.0216(15) -0.0062(12) 0.0120(12) -0.0034(12) C23 0.0268(15) 0.0331(17) 0.0210(15) -0.0058(13) 0.0126(13) -0.0030(12) C24 0.0268(15) 0.0302(16) 0.0182(15) -0.0050(13) 0.0026(12) 0.0023(12) Sb2 0.01851(10) 0.01549(10) 0.01486(10) -0.00049(7) 0.00453(8) -0.00253(7) Cl1 0.0266(3) 0.0334(4) 0.0265(4) 0.0068(3) 0.0127(3) -0.0002(3) Cl2 0.0385(4) 0.0205(3) 0.0285(4) -0.0048(3) 0.0199(3) -0.0029(3) Cl3 0.0444(4) 0.0158(3) 0.0217(4) 0.0024(3) 0.0094(3) 0.0030(3) Cl4 0.0231(3) 0.0177(3) 0.0195(3) -0.0035(3) 0.0051(3) -0.0038(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sb1 N2 2.023(2) . ? Sb1 N1 2.025(2) . ? Sb1 Cl1 3.4326(7) . ? Sb1 Cl2 3.6927(7) 3_656 ? Sb1 Cl4 3.7188(7) 3_656 ? Sb1 Cl2 3.8057(8) 1_655 ? Sb1 Cl4 3.9435(7) 1_655 ? N1 C1 1.356(3) . ? N1 C11 1.499(3) . ? C1 C2 1.360(4) . ? C1 H1 0.9500 . ? C2 N2 1.353(3) . ? C2 H2 0.9500 . ? N2 C21 1.497(3) . ? C11 C12 1.519(4) . ? C11 C13 1.524(4) . ? C11 C14 1.528(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C21 C23 1.523(4) . ? C21 C24 1.526(4) . ? C21 C22 1.528(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? Sb2 Cl4 2.3624(6) . ? Sb2 Cl3 2.4210(7) . ? Sb2 Cl2 2.5173(7) . ? Sb2 Cl1 2.6994(7) . ? Sb2 Cl1 3.0538(7) 3_656 ? Cl1 Sb2 3.0538(7) 3_656 ? 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 Sb1 N1 79.71(9) . . ? N2 Sb1 Cl1 113.31(6) . . ? N1 Sb1 Cl1 100.92(6) . . ? N2 Sb1 Cl2 113.88(6) . 3_656 ? N1 Sb1 Cl2 165.04(6) . 3_656 ? Cl1 Sb1 Cl2 68.592(17) . 3_656 ? N2 Sb1 Cl4 167.76(6) . 3_656 ? N1 Sb1 Cl4 111.47(6) . 3_656 ? Cl1 Sb1 Cl4 60.865(15) . 3_656 ? Cl2 Sb1 Cl4 54.466(15) 3_656 3_656 ? N2 Sb1 Cl2 117.03(6) . 1_655 ? N1 Sb1 Cl2 87.48(6) . 1_655 ? Cl1 Sb1 Cl2 129.660(16) . 1_655 ? Cl2 Sb1 Cl2 91.365(16) 3_656 1_655 ? Cl4 Sb1 Cl2 69.815(14) 3_656 1_655 ? N2 Sb1 Cl4 84.03(6) . 1_655 ? N1 Sb1 Cl4 121.13(6) . 1_655 ? Cl1 Sb1 Cl4 137.161(16) . 1_655 ? Cl2 Sb1 Cl4 68.570(15) 3_656 1_655 ? Cl4 Sb1 Cl4 93.773(14) 3_656 1_655 ? Cl2 Sb1 Cl4 51.874(14) 1_655 1_655 ? C1 N1 C11 121.1(2) . . ? C1 N1 Sb1 112.90(17) . . ? C11 N1 Sb1 125.74(16) . . ? N1 C1 C2 117.1(2) . . ? N1 C1 H1 121.4 . . ? C2 C1 H1 121.4 . . ? N2 C2 C1 117.1(2) . . ? N2 C2 H2 121.5 . . ? C1 C2 H2 121.5 . . ? C2 N2 C21 120.5(2) . . ? C2 N2 Sb1 113.09(17) . . ? C21 N2 Sb1 126.42(17) . . ? N1 C11 C12 108.6(2) . . ? N1 C11 C13 109.6(2) . . ? C12 C11 C13 110.3(2) . . ? N1 C11 C14 108.1(2) . . ? C12 C11 C14 109.7(2) . . ? C13 C11 C14 110.4(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C21 C23 108.3(2) . . ? N2 C21 C24 109.6(2) . . ? C23 C21 C24 111.1(2) . . ? N2 C21 C22 107.8(2) . . ? C23 C21 C22 110.7(2) . . ? C24 C21 C22 109.2(2) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? Cl4 Sb2 Cl3 91.61(2) . . ? Cl4 Sb2 Cl2 88.00(2) . . ? Cl3 Sb2 Cl2 92.16(2) . . ? Cl4 Sb2 Cl1 85.80(2) . . ? Cl3 Sb2 Cl1 90.43(2) . . ? Cl2 Sb2 Cl1 173.35(2) . . ? Cl4 Sb2 Cl1 83.14(2) . 3_656 ? Cl3 Sb2 Cl1 173.26(2) . 3_656 ? Cl2 Sb2 Cl1 91.88(2) . 3_656 ? Cl1 Sb2 Cl1 84.98(2) . 3_656 ? Sb2 Cl1 Sb2 95.02(2) . 3_656 ? Sb2 Cl1 Sb1 135.82(3) . . ? Sb2 Cl1 Sb1 87.962(17) 3_656 . ? 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 N2 Sb1 N1 C1 -2.54(17) . . . . ? Cl1 Sb1 N1 C1 -114.53(17) . . . . ? Cl2 Sb1 N1 C1 -158.63(17) 3_656 . . . ? Cl4 Sb1 N1 C1 -177.34(16) 3_656 . . . ? Cl2 Sb1 N1 C1 115.52(17) 1_655 . . . ? Cl4 Sb1 N1 C1 73.98(18) 1_655 . . . ? N2 Sb1 N1 C11 171.3(2) . . . . ? Cl1 Sb1 N1 C11 59.35(19) . . . . ? Cl2 Sb1 N1 C11 15.2(4) 3_656 . . . ? Cl4 Sb1 N1 C11 -3.5(2) 3_656 . . . ? Cl2 Sb1 N1 C11 -70.61(18) 1_655 . . . ? Cl4 Sb1 N1 C11 -112.14(17) 1_655 . . . ? C11 N1 C1 C2 -172.4(2) . . . . ? Sb1 N1 C1 C2 1.8(3) . . . . ? N1 C1 C2 N2 0.7(4) . . . . ? C1 C2 N2 C21 176.8(2) . . . . ? C1 C2 N2 Sb1 -2.9(3) . . . . ? N1 Sb1 N2 C2 2.90(18) . . . . ? Cl1 Sb1 N2 C2 100.45(17) . . . . ? Cl2 Sb1 N2 C2 176.34(16) 3_656 . . . ? Cl4 Sb1 N2 C2 159.5(2) 3_656 . . . ? Cl2 Sb1 N2 C2 -78.89(18) 1_655 . . . ? Cl4 Sb1 N2 C2 -120.28(17) 1_655 . . . ? N1 Sb1 N2 C21 -176.8(2) . . . . ? Cl1 Sb1 N2 C21 -79.2(2) . . . . ? Cl2 Sb1 N2 C21 -3.3(2) 3_656 . . . ? Cl4 Sb1 N2 C21 -20.2(4) 3_656 . . . ? Cl2 Sb1 N2 C21 101.45(19) 1_655 . . . ? Cl4 Sb1 N2 C21 60.06(19) 1_655 . . . ? C1 N1 C11 C12 -174.0(2) . . . . ? Sb1 N1 C11 C12 12.5(3) . . . . ? C1 N1 C11 C13 -53.5(3) . . . . ? Sb1 N1 C11 C13 133.1(2) . . . . ? C1 N1 C11 C14 67.0(3) . . . . ? Sb1 N1 C11 C14 -106.5(2) . . . . ? C2 N2 C21 C23 65.2(3) . . . . ? Sb1 N2 C21 C23 -115.2(2) . . . . ? C2 N2 C21 C24 -56.2(3) . . . . ? Sb1 N2 C21 C24 123.5(2) . . . . ? C2 N2 C21 C22 -175.0(2) . . . . ? Sb1 N2 C21 C22 4.6(3) . . . . ? Cl4 Sb2 Cl1 Sb2 -83.46(2) . . . 3_656 ? Cl3 Sb2 Cl1 Sb2 -175.05(2) . . . 3_656 ? Cl2 Sb2 Cl1 Sb2 -62.0(2) . . . 3_656 ? Cl1 Sb2 Cl1 Sb2 0.0 3_656 . . 3_656 ? Cl4 Sb2 Cl1 Sb1 -175.70(4) . . . . ? Cl3 Sb2 Cl1 Sb1 92.71(4) . . . . ? Cl2 Sb2 Cl1 Sb1 -154.26(19) . . . . ? Cl1 Sb2 Cl1 Sb1 -92.24(4) 3_656 . . . ? N2 Sb1 Cl1 Sb2 -130.20(7) . . . . ? N1 Sb1 Cl1 Sb2 -46.80(7) . . . . ? Cl2 Sb1 Cl1 Sb2 122.07(4) 3_656 . . . ? Cl4 Sb1 Cl1 Sb2 61.82(3) 3_656 . . . ? Cl2 Sb1 Cl1 Sb2 49.04(4) 1_655 . . . ? Cl4 Sb1 Cl1 Sb2 122.46(3) 1_655 . . . ? N2 Sb1 Cl1 Sb2 134.70(7) . . . 3_656 ? N1 Sb1 Cl1 Sb2 -141.90(6) . . . 3_656 ? Cl2 Sb1 Cl1 Sb2 26.973(16) 3_656 . . 3_656 ? Cl4 Sb1 Cl1 Sb2 -33.282(14) 3_656 . . 3_656 ? Cl2 Sb1 Cl1 Sb2 -46.06(3) 1_655 . . 3_656 ? Cl4 Sb1 Cl1 Sb2 27.36(3) 1_655 . . 3_656 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 Cl2 0.95 2.76 3.610(3) 148.8 4_665 C12 H12A Cl2 0.98 3.01 3.951(3) 162.2 1_655 C2 H2 Cl3 0.95 2.77 3.655(3) 156.0 4_665 C12 H12B Cl4 0.98 2.90 3.558(3) 125.2 3_656 C22 H22A Cl4 0.98 2.97 3.899(3) 158.2 1_655 C23 H23C Cl4 0.98 2.86 3.815(3) 165.1 3_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.556 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.078 #============================================================================== data_gudat57m _database_code_depnum_ccdc_archive 'CCDC 242442' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Di-tert.butyl-diazadiene antimopny trichloride, antimony trichloride adduct ; _chemical_name_common ;N,N'-Di-tert.butyl-diazadiene antimopny trichloride, antimony trichloride adduct ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H20 Cl3 N2 Sb - Sb Cl3' _chemical_formula_sum 'C10 H20 Cl6 N2 Sb2' _chemical_formula_weight 624.48 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 '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 _symmetry_Int_Tables_number 15 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 12.0617(1) _cell_length_b 17.4255(2) _cell_length_c 19.3913(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.081(1) _cell_angle_gamma 90.00 _cell_volume 3985.42(7) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4678 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.082 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2384 _exptl_absorpt_coefficient_mu 3.508 _exptl_absorpt_correction_type 'empirical from multiple refl.' _exptl_absorpt_correction_T_min 0.5753 _exptl_absorpt_correction_T_max 0.7920 _exptl_absorpt_process_details 'MULABS (Platon, cf. Blessing, 1995)' _exptl_special_details ; dx = 40 mm, 80 sec./deg., 1 deg. 9 sets, 839 frames, mos.= 0.500(1) deg. ; _diffrn_ambient_temperature 123(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 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 34881 _diffrn_reflns_av_R_equivalents 0.0705 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3512 _reflns_number_gt 2913 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _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^)+(0.0155P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3512 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0182 _refine_ls_wR_factor_ref 0.0406 _refine_ls_wR_factor_gt 0.0391 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.530209(15) 0.234730(10) 0.604214(9) 0.01759(6) Uani 1 1 d . . . Cl1 Cl 0.55971(6) 0.22373(4) 0.48683(3) 0.02507(17) Uani 1 1 d . . . Cl2 Cl 0.38651(6) 0.33941(4) 0.55803(3) 0.02583(17) Uani 1 1 d . . . Cl3 Cl 0.36523(6) 0.13794(4) 0.56569(4) 0.02803(17) Uani 1 1 d . . . N1 N 0.69539(18) 0.14855(12) 0.62711(10) 0.0161(5) Uani 1 1 d . . . C11 C 0.6908(2) 0.06288(14) 0.63700(13) 0.0197(6) Uani 1 1 d . . . C12 C 0.8079(2) 0.02615(15) 0.65629(14) 0.0257(7) Uani 1 1 d . . . H12A H 0.8507 0.0493 0.6998 0.038 Uiso 1 1 calc R . . H12B H 0.8483 0.0346 0.6181 0.038 Uiso 1 1 calc R . . H12C H 0.7998 -0.0291 0.6634 0.038 Uiso 1 1 calc R . . C13 C 0.6261(2) 0.05181(15) 0.69691(13) 0.0248(7) Uani 1 1 d . . . H13A H 0.6701 0.0741 0.7405 0.037 Uiso 1 1 calc R . . H13B H 0.6148 -0.0031 0.7039 0.037 Uiso 1 1 calc R . . H13C H 0.5523 0.0774 0.6844 0.037 Uiso 1 1 calc R . . C14 C 0.6238(2) 0.02830(15) 0.56856(13) 0.0241(7) Uani 1 1 d . . . H14A H 0.5491 0.0527 0.5562 0.036 Uiso 1 1 calc R . . H14B H 0.6144 -0.0270 0.5749 0.036 Uiso 1 1 calc R . . H14C H 0.6648 0.0369 0.5306 0.036 Uiso 1 1 calc R . . C1 C 0.7887(2) 0.18558(15) 0.64267(12) 0.0190(6) Uani 1 1 d . . . H1 H 0.8575 0.1581 0.6577 0.023 Uiso 1 1 calc R . . C2 C 0.7923(2) 0.26979(14) 0.63784(12) 0.0173(6) Uani 1 1 d . . . H2 H 0.8634 0.2953 0.6498 0.021 Uiso 1 1 calc R . . N2 N 0.70229(18) 0.30953(12) 0.61803(10) 0.0175(5) Uani 1 1 d . . . C21 C 0.7076(2) 0.39608(15) 0.61587(13) 0.0208(6) Uani 1 1 d . . . C22 C 0.6396(2) 0.42369(15) 0.67025(14) 0.0264(7) Uani 1 1 d . . . H22A H 0.5623 0.4032 0.6579 0.040 Uiso 1 1 calc R . . H22B H 0.6368 0.4799 0.6701 0.040 Uiso 1 1 calc R . . H22C H 0.6765 0.4056 0.7173 0.040 Uiso 1 1 calc R . . C23 C 0.6515(2) 0.41994(15) 0.54076(13) 0.0275(7) Uani 1 1 d . . . H23A H 0.5742 0.3994 0.5289 0.041 Uiso 1 1 calc R . . H23B H 0.6955 0.3996 0.5077 0.041 Uiso 1 1 calc R . . H23C H 0.6490 0.4761 0.5376 0.041 Uiso 1 1 calc R . . C24 C 0.8276(2) 0.42727(15) 0.63436(14) 0.0259(7) Uani 1 1 d . . . H24A H 0.8631 0.4120 0.6826 0.039 Uiso 1 1 calc R . . H24B H 0.8256 0.4834 0.6310 0.039 Uiso 1 1 calc R . . H24C H 0.8715 0.4066 0.6014 0.039 Uiso 1 1 calc R . . Sb2 Sb 0.196162(16) 0.244268(10) 0.613595(9) 0.01923(6) Uani 1 1 d . . . Cl4 Cl 0.35007(6) 0.24218(4) 0.71505(3) 0.02665(17) Uani 1 1 d . . . Cl5 Cl 0.10280(6) 0.33396(4) 0.67724(4) 0.03089(18) Uani 1 1 d . . . Cl6 Cl 0.10317(6) 0.13790(4) 0.65378(4) 0.03438(19) 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 Sb1 0.01976(11) 0.01947(11) 0.01328(10) -0.00069(7) 0.00286(8) 0.00097(8) Cl1 0.0275(4) 0.0341(4) 0.0134(3) -0.0024(3) 0.0037(3) 0.0036(3) Cl2 0.0259(4) 0.0245(4) 0.0260(4) 0.0026(3) 0.0027(3) 0.0048(3) Cl3 0.0252(4) 0.0237(4) 0.0333(4) -0.0063(3) 0.0020(3) -0.0015(3) N1 0.0223(13) 0.0150(12) 0.0116(11) -0.0004(9) 0.0052(10) 0.0015(10) C11 0.0283(17) 0.0146(15) 0.0163(14) 0.0013(11) 0.0051(13) 0.0001(13) C12 0.0326(19) 0.0173(16) 0.0253(16) 0.0012(12) 0.0021(14) 0.0027(14) C13 0.0336(18) 0.0197(16) 0.0213(16) 0.0012(12) 0.0062(14) -0.0021(13) C14 0.0328(18) 0.0176(16) 0.0214(15) -0.0030(12) 0.0043(14) -0.0034(13) C1 0.0221(16) 0.0211(16) 0.0135(14) -0.0008(11) 0.0030(12) 0.0035(13) C2 0.0188(16) 0.0227(16) 0.0107(14) -0.0037(11) 0.0039(12) -0.0046(13) N2 0.0241(14) 0.0186(13) 0.0100(11) -0.0012(9) 0.0044(10) -0.0022(11) C21 0.0307(18) 0.0117(14) 0.0190(15) 0.0009(11) 0.0026(13) 0.0000(12) C22 0.0358(19) 0.0166(16) 0.0273(16) -0.0041(12) 0.0081(14) 0.0032(14) C23 0.0369(19) 0.0226(17) 0.0222(16) 0.0069(13) 0.0045(14) -0.0024(14) C24 0.0344(19) 0.0167(16) 0.0265(16) 0.0007(12) 0.0061(14) -0.0031(14) Sb2 0.02128(12) 0.01985(11) 0.01589(11) 0.00034(7) 0.00234(8) -0.00025(8) Cl4 0.0238(4) 0.0379(5) 0.0171(4) 0.0018(3) 0.0018(3) 0.0018(3) Cl5 0.0312(5) 0.0301(4) 0.0291(4) -0.0115(3) 0.0012(3) 0.0049(3) Cl6 0.0320(5) 0.0233(4) 0.0460(5) 0.0109(3) 0.0039(4) -0.0037(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 Sb1 Cl1 2.3841(6) . ? Sb1 N2 2.418(2) . ? Sb1 N1 2.460(2) . ? Sb1 Cl2 2.5464(7) . ? Sb1 Cl3 2.5962(7) . ? Sb1 Cl4 3.3633(6) . ? Cl1 Sb2 3.3336(7) 7_556 ? Cl2 Sb2 3.1963(7) . ? Cl3 Sb2 3.0408(7) . ? N1 C1 1.278(3) . ? N1 C11 1.508(3) . ? C11 C12 1.524(4) . ? C11 C14 1.526(3) . ? C11 C13 1.541(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C1 C2 1.472(3) . ? C1 H1 0.9500 . ? C2 N2 1.277(3) . ? C2 H2 0.9500 . ? N2 C21 1.510(3) . ? C21 C24 1.517(4) . ? C21 C23 1.529(3) . ? C21 C22 1.542(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? Sb2 Cl6 2.3804(7) . ? Sb2 Cl4 2.4061(7) . ? Sb2 Cl5 2.4116(7) . ? Sb2 Cl1 3.3336(7) 7_556 ? 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 Cl1 Sb1 N2 81.54(5) . . ? Cl1 Sb1 N1 81.15(5) . . ? N2 Sb1 N1 70.43(7) . . ? Cl1 Sb1 Cl2 87.05(2) . . ? N2 Sb1 Cl2 99.10(6) . . ? N1 Sb1 Cl2 165.19(5) . . ? Cl1 Sb1 Cl3 86.08(2) . . ? N2 Sb1 Cl3 166.07(5) . . ? N1 Sb1 Cl3 101.44(5) . . ? Cl2 Sb1 Cl3 86.55(2) . . ? Cl1 Sb1 Cl4 149.17(2) . . ? N2 Sb1 Cl4 124.25(5) . . ? N1 Sb1 Cl4 121.02(4) . . ? Cl2 Sb1 Cl4 73.372(19) . . ? Cl3 Sb1 Cl4 69.522(19) . . ? Sb1 Cl1 Sb2 103.85(2) . 7_556 ? Sb1 Cl2 Sb2 89.654(19) . . ? Sb1 Cl3 Sb2 92.23(2) . . ? C1 N1 C11 121.6(2) . . ? C1 N1 Sb1 112.00(17) . . ? C11 N1 Sb1 125.28(16) . . ? N1 C11 C12 113.0(2) . . ? N1 C11 C14 107.9(2) . . ? C12 C11 C14 110.0(2) . . ? N1 C11 C13 104.93(19) . . ? C12 C11 C13 110.6(2) . . ? C14 C11 C13 110.3(2) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C1 C2 121.6(3) . . ? N1 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? N2 C2 C1 121.7(2) . . ? N2 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C2 N2 C21 120.8(2) . . ? C2 N2 Sb1 113.39(17) . . ? C21 N2 Sb1 125.13(16) . . ? N2 C21 C24 113.3(2) . . ? N2 C21 C23 106.6(2) . . ? C24 C21 C23 109.7(2) . . ? N2 C21 C22 105.13(19) . . ? C24 C21 C22 110.1(2) . . ? C23 C21 C22 112.0(2) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? Cl6 Sb2 Cl4 93.23(3) . . ? Cl6 Sb2 Cl5 91.98(3) . . ? Cl4 Sb2 Cl5 87.38(2) . . ? Cl6 Sb2 Cl3 91.01(2) . . ? Cl4 Sb2 Cl3 77.80(2) . . ? Cl5 Sb2 Cl3 165.02(2) . . ? Cl6 Sb2 Cl2 159.25(2) . . ? Cl4 Sb2 Cl2 78.33(2) . . ? Cl5 Sb2 Cl2 106.36(2) . . ? Cl3 Sb2 Cl2 68.787(18) . . ? Cl6 Sb2 Cl1 83.07(2) . 7_556 ? Cl4 Sb2 Cl1 160.34(2) . 7_556 ? Cl5 Sb2 Cl1 73.51(2) . 7_556 ? Cl3 Sb2 Cl1 121.435(18) . 7_556 ? Cl2 Sb2 Cl1 111.029(17) . 7_556 ? Sb2 Cl4 Sb1 88.232(19) . . ? 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 N2 Sb1 Cl1 Sb2 -134.92(6) . . . 7_556 ? N1 Sb1 Cl1 Sb2 153.72(5) . . . 7_556 ? Cl2 Sb1 Cl1 Sb2 -35.26(2) . . . 7_556 ? Cl3 Sb1 Cl1 Sb2 51.48(2) . . . 7_556 ? Cl4 Sb1 Cl1 Sb2 14.53(5) . . . 7_556 ? Cl1 Sb1 Cl2 Sb2 122.81(2) . . . . ? N2 Sb1 Cl2 Sb2 -156.25(4) . . . . ? N1 Sb1 Cl2 Sb2 159.9(2) . . . . ? Cl3 Sb1 Cl2 Sb2 36.561(19) . . . . ? Cl4 Sb1 Cl2 Sb2 -33.087(16) . . . . ? Cl1 Sb1 Cl3 Sb2 -126.07(2) . . . . ? N2 Sb1 Cl3 Sb2 -153.3(2) . . . . ? N1 Sb1 Cl3 Sb2 153.79(4) . . . . ? Cl2 Sb1 Cl3 Sb2 -38.80(2) . . . . ? Cl4 Sb1 Cl3 Sb2 34.731(16) . . . . ? Cl1 Sb1 N1 C1 91.47(15) . . . . ? N2 Sb1 N1 C1 7.36(15) . . . . ? Cl2 Sb1 N1 C1 53.9(3) . . . . ? Cl3 Sb1 N1 C1 175.61(15) . . . . ? Cl4 Sb1 N1 C1 -111.54(15) . . . . ? Cl1 Sb1 N1 C11 -100.53(17) . . . . ? N2 Sb1 N1 C11 175.36(18) . . . . ? Cl2 Sb1 N1 C11 -138.09(18) . . . . ? Cl3 Sb1 N1 C11 -16.39(17) . . . . ? Cl4 Sb1 N1 C11 56.47(18) . . . . ? C1 N1 C11 C12 -8.4(3) . . . . ? Sb1 N1 C11 C12 -175.32(15) . . . . ? C1 N1 C11 C14 -130.3(2) . . . . ? Sb1 N1 C11 C14 62.8(2) . . . . ? C1 N1 C11 C13 112.1(2) . . . . ? Sb1 N1 C11 C13 -54.8(3) . . . . ? C11 N1 C1 C2 -175.57(19) . . . . ? Sb1 N1 C1 C2 -7.1(3) . . . . ? N1 C1 C2 N2 0.1(3) . . . . ? C1 C2 N2 C21 177.88(19) . . . . ? C1 C2 N2 Sb1 7.1(3) . . . . ? Cl1 Sb1 N2 C2 -90.92(16) . . . . ? N1 Sb1 N2 C2 -7.37(15) . . . . ? Cl2 Sb1 N2 C2 -176.53(15) . . . . ? Cl3 Sb1 N2 C2 -63.4(3) . . . . ? Cl4 Sb1 N2 C2 107.45(15) . . . . ? Cl1 Sb1 N2 C21 98.73(17) . . . . ? N1 Sb1 N2 C21 -177.71(18) . . . . ? Cl2 Sb1 N2 C21 13.12(17) . . . . ? Cl3 Sb1 N2 C21 126.3(2) . . . . ? Cl4 Sb1 N2 C21 -62.90(18) . . . . ? C2 N2 C21 C24 3.8(3) . . . . ? Sb1 N2 C21 C24 173.45(15) . . . . ? C2 N2 C21 C23 124.5(2) . . . . ? Sb1 N2 C21 C23 -65.8(2) . . . . ? C2 N2 C21 C22 -116.5(2) . . . . ? Sb1 N2 C21 C22 53.2(3) . . . . ? Sb1 Cl3 Sb2 Cl6 -142.84(3) . . . . ? Sb1 Cl3 Sb2 Cl4 -49.76(2) . . . . ? Sb1 Cl3 Sb2 Cl5 -41.31(9) . . . . ? Sb1 Cl3 Sb2 Cl2 32.310(19) . . . . ? Sb1 Cl3 Sb2 Cl1 134.660(19) . . . 7_556 ? Sb1 Cl2 Sb2 Cl6 -19.19(7) . . . . ? Sb1 Cl2 Sb2 Cl4 48.30(2) . . . . ? Sb1 Cl2 Sb2 Cl5 132.03(2) . . . . ? Sb1 Cl2 Sb2 Cl3 -32.994(19) . . . . ? Sb1 Cl2 Sb2 Cl1 -149.747(18) . . . 7_556 ? Cl6 Sb2 Cl4 Sb1 126.43(2) . . . . ? Cl5 Sb2 Cl4 Sb1 -141.73(2) . . . . ? Cl3 Sb2 Cl4 Sb1 36.089(16) . . . . ? Cl2 Sb2 Cl4 Sb1 -34.438(15) . . . . ? Cl1 Sb2 Cl4 Sb1 -155.17(5) 7_556 . . . ? Cl1 Sb1 Cl4 Sb2 -6.23(5) . . . . ? N2 Sb1 Cl4 Sb2 136.30(6) . . . . ? N1 Sb1 Cl4 Sb2 -137.33(6) . . . . ? Cl2 Sb1 Cl4 Sb2 46.51(2) . . . . ? Cl3 Sb1 Cl4 Sb2 -46.04(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 Cl6 0.95 3.00 3.844(3) 148.8 1_655 C2 H2 Cl5 0.95 2.90 3.829(3) 164.9 1_655 C22 H22B Cl6 0.98 2.79 3.764(3) 172.0 3 C13 H13B Cl5 0.98 2.88 3.820(3) 160.0 3_545 C24 H24A Cl5 0.98 2.99 3.926(3) 160.1 2_656 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.414 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.080 #============================================================================== data_gudat60m _database_code_depnum_ccdc_archive 'CCDC 242443' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-Di-tert.butyl-2-chloro-1,3,2-diazastibolenium trisfluoromethane sulfonate ; _chemical_name_common ;1,3-Di-tert.butyl-2-chloro-1,3,2-diazastibolenium trisfluoromethane sulfonate ; _chemical_melting_point ? _chemical_formula_moiety 'C10H20N2Sb + CF3SO3 + CH2Cl2' _chemical_formula_sum 'C12 H22 Cl2 F3 N2 O3 S Sb' _chemical_formula_weight 524.03 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' Sb Sb -0.5866 1.5461 '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 P2(1)/c _symmetry_Int_Tables_number 14 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 11.0192(1) _cell_length_b 10.3184(1) _cell_length_c 18.6936(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.138(1) _cell_angle_gamma 90.00 _cell_volume 2061.09(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4964 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 1.737 _exptl_absorpt_correction_type 'Empirical from multiple refl.' _exptl_absorpt_correction_T_min 0.4978 _exptl_absorpt_correction_T_max 0.8459 _exptl_absorpt_process_details Mulabs _exptl_special_details ; dx = 40 mm; 60 sec./deg.; 1 deg.; 6 sets; 869 frames; mos. 678(1) deg. ; _diffrn_ambient_temperature 123(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 'Nonius KappaCCD' _diffrn_measurement_method 'Rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 32263 _diffrn_reflns_av_R_equivalents 0.0744 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3603 _reflns_number_gt 3309 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics xp _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^)+(0.0298P)^2^+1.5712P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3603 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0606 _refine_ls_wR_factor_gt 0.0595 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 Sb1 Sb 0.675013(13) 0.588885(15) 0.576023(8) 0.01829(7) Uani 1 1 d . . . N2 N 0.82873(17) 0.66216(18) 0.55026(10) 0.0174(4) Uani 1 1 d . . . C3 C 0.9374(2) 0.6260(2) 0.59735(13) 0.0216(5) Uani 1 1 d . . . H3 H 1.0163 0.6552 0.5916 0.026 Uiso 1 1 calc R . . C4 C 0.9276(2) 0.5454(2) 0.65348(14) 0.0236(5) Uani 1 1 d . . . H4 H 0.9995 0.5150 0.6886 0.028 Uiso 1 1 calc R . . N5 N 0.81110(18) 0.51061(19) 0.65695(11) 0.0196(4) Uani 1 1 d . . . C6 C 0.8289(2) 0.7484(2) 0.48579(13) 0.0212(5) Uani 1 1 d . . . C7 C 0.9026(3) 0.8716(3) 0.51376(15) 0.0299(6) Uani 1 1 d . . . H7A H 0.9894 0.8488 0.5376 0.045 Uiso 1 1 calc R . . H7B H 0.8645 0.9151 0.5494 0.045 Uiso 1 1 calc R . . H7C H 0.9012 0.9298 0.4721 0.045 Uiso 1 1 calc R . . C8 C 0.6934(2) 0.7835(2) 0.44860(14) 0.0251(5) Uani 1 1 d . . . H8A H 0.6465 0.7044 0.4307 0.038 Uiso 1 1 calc R . . H8B H 0.6918 0.8417 0.4069 0.038 Uiso 1 1 calc R . . H8C H 0.6552 0.8269 0.4843 0.038 Uiso 1 1 calc R . . C9 C 0.8879(3) 0.6741(3) 0.43225(14) 0.0291(6) Uani 1 1 d . . . H9A H 0.8387 0.5960 0.4154 0.044 Uiso 1 1 calc R . . H9B H 0.9737 0.6495 0.4572 0.044 Uiso 1 1 calc R . . H9C H 0.8893 0.7293 0.3898 0.044 Uiso 1 1 calc R . . C10 C 0.7900(2) 0.4193(2) 0.71527(14) 0.0243(6) Uani 1 1 d . . . C11 C 0.8524(3) 0.2904(2) 0.70748(15) 0.0302(6) Uani 1 1 d . . . H11A H 0.9427 0.3035 0.7147 0.045 Uiso 1 1 calc R . . H11B H 0.8175 0.2550 0.6581 0.045 Uiso 1 1 calc R . . H11C H 0.8373 0.2295 0.7446 0.045 Uiso 1 1 calc R . . C12 C 0.6496(3) 0.4005(3) 0.70391(17) 0.0370(7) Uani 1 1 d . . . H12A H 0.6102 0.4840 0.7089 0.056 Uiso 1 1 calc R . . H12B H 0.6338 0.3400 0.7410 0.056 Uiso 1 1 calc R . . H12C H 0.6145 0.3652 0.6545 0.056 Uiso 1 1 calc R . . C13 C 0.8462(3) 0.4798(3) 0.79086(15) 0.0392(7) Uani 1 1 d . . . H13A H 0.9365 0.4915 0.7973 0.059 Uiso 1 1 calc R . . H13B H 0.8311 0.4225 0.8296 0.059 Uiso 1 1 calc R . . H13C H 0.8069 0.5641 0.7941 0.059 Uiso 1 1 calc R . . S1 S 0.35498(5) 0.65178(6) 0.61859(3) 0.01968(13) Uani 1 1 d . . . O1 O 0.37959(16) 0.53231(17) 0.58449(10) 0.0271(4) Uani 1 1 d . . . O2 O 0.46362(16) 0.70841(18) 0.66714(10) 0.0302(4) Uani 1 1 d . . . O3 O 0.24315(17) 0.65197(19) 0.64547(10) 0.0316(4) Uani 1 1 d . . . C1 C 0.3169(2) 0.7644(3) 0.54105(15) 0.0305(6) Uani 1 1 d . . . F1 F 0.40842(16) 0.77010(17) 0.50590(9) 0.0428(4) Uani 1 1 d . . . F2 F 0.21341(16) 0.7273(2) 0.49164(9) 0.0493(5) Uani 1 1 d . . . F3 F 0.29781(19) 0.88344(17) 0.56299(11) 0.0520(5) Uani 1 1 d . . . C1S C 0.6569(3) 0.9436(3) 0.70597(17) 0.0388(7) Uani 1 1 d . . . H1S1 H 0.5911 0.8830 0.7130 0.047 Uiso 1 1 calc R . . H1S2 H 0.6686 1.0106 0.7450 0.047 Uiso 1 1 calc R . . Cl1S Cl 0.79882(7) 0.85819(8) 0.71356(4) 0.0468(2) Uani 1 1 d . . . Cl2S Cl 0.60950(9) 1.01762(9) 0.61847(5) 0.0615(3) 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 Sb1 0.01307(11) 0.02278(11) 0.01893(11) 0.00307(6) 0.00371(7) -0.00106(6) N2 0.0160(10) 0.0160(10) 0.0207(10) -0.0003(8) 0.0055(8) -0.0007(8) C3 0.0144(12) 0.0217(12) 0.0284(13) 0.0009(10) 0.0049(10) -0.0020(10) C4 0.0180(12) 0.0248(12) 0.0255(13) 0.0022(11) 0.0004(10) 0.0032(10) N5 0.0186(10) 0.0214(10) 0.0189(10) 0.0012(8) 0.0047(8) 0.0010(8) C6 0.0221(12) 0.0181(12) 0.0247(13) 0.0030(10) 0.0084(10) -0.0031(9) C7 0.0300(15) 0.0204(13) 0.0382(16) 0.0027(11) 0.0061(12) -0.0079(11) C8 0.0236(13) 0.0221(13) 0.0280(13) 0.0074(10) 0.0034(11) -0.0005(10) C9 0.0301(14) 0.0328(14) 0.0281(14) 0.0005(11) 0.0144(11) -0.0030(11) C10 0.0263(14) 0.0267(14) 0.0203(13) 0.0072(10) 0.0064(11) 0.0013(10) C11 0.0341(15) 0.0252(14) 0.0305(14) 0.0083(11) 0.0067(12) 0.0002(11) C12 0.0284(16) 0.0470(18) 0.0393(17) 0.0217(13) 0.0153(13) 0.0020(12) C13 0.0530(19) 0.0420(18) 0.0225(14) 0.0034(13) 0.0092(13) 0.0019(14) S1 0.0164(3) 0.0212(3) 0.0215(3) -0.0028(2) 0.0047(2) -0.0009(2) O1 0.0289(10) 0.0218(9) 0.0313(10) -0.0048(8) 0.0085(8) -0.0012(7) O2 0.0250(10) 0.0321(10) 0.0306(10) -0.0081(8) 0.0014(8) -0.0043(8) O3 0.0228(10) 0.0423(12) 0.0331(10) -0.0008(9) 0.0134(8) 0.0001(8) C1 0.0264(14) 0.0319(15) 0.0346(15) 0.0052(12) 0.0100(12) 0.0082(11) F1 0.0381(9) 0.0521(11) 0.0441(10) 0.0222(8) 0.0214(8) 0.0111(8) F2 0.0321(9) 0.0734(13) 0.0353(9) 0.0107(9) -0.0055(8) 0.0082(9) F3 0.0613(13) 0.0287(9) 0.0701(13) 0.0105(9) 0.0239(10) 0.0184(8) C1S 0.0360(17) 0.0381(16) 0.0428(18) -0.0108(14) 0.0106(14) -0.0068(13) Cl1S 0.0359(4) 0.0505(5) 0.0457(4) -0.0126(4) -0.0057(3) 0.0006(3) Cl2S 0.0589(6) 0.0473(5) 0.0673(6) 0.0132(4) -0.0055(4) -0.0019(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 Sb1 N2 2.0177(19) . ? Sb1 N5 2.0202(19) . ? N2 C3 1.354(3) . ? N2 C6 1.499(3) . ? C3 C4 1.364(4) . ? C3 H3 0.9500 . ? C4 N5 1.349(3) . ? C4 H4 0.9500 . ? N5 C10 1.502(3) . ? C6 C9 1.527(3) . ? C6 C8 1.528(3) . ? C6 C7 1.530(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C12 1.521(4) . ? C10 C11 1.521(4) . ? C10 C13 1.530(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? S1 O2 1.4378(18) . ? S1 O3 1.4400(18) . ? S1 O1 1.4436(18) . ? S1 C1 1.825(3) . ? C1 F3 1.328(3) . ? C1 F1 1.333(3) . ? C1 F2 1.336(3) . ? C1S Cl2S 1.765(3) . ? C1S Cl1S 1.770(3) . ? C1S H1S1 0.9900 . ? C1S H1S2 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 N2 Sb1 N5 79.38(8) . . ? C3 N2 C6 120.79(19) . . ? C3 N2 Sb1 113.72(15) . . ? C6 N2 Sb1 125.49(14) . . ? N2 C3 C4 116.4(2) . . ? N2 C3 H3 121.8 . . ? C4 C3 H3 121.8 . . ? N5 C4 C3 117.0(2) . . ? N5 C4 H4 121.5 . . ? C3 C4 H4 121.5 . . ? C4 N5 C10 121.3(2) . . ? C4 N5 Sb1 113.49(16) . . ? C10 N5 Sb1 125.18(15) . . ? N2 C6 C9 108.28(19) . . ? N2 C6 C8 108.27(19) . . ? C9 C6 C8 110.2(2) . . ? N2 C6 C7 108.87(19) . . ? C9 C6 C7 111.4(2) . . ? C8 C6 C7 109.7(2) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N5 C10 C12 108.1(2) . . ? N5 C10 C11 109.0(2) . . ? C12 C10 C11 110.1(2) . . ? N5 C10 C13 108.4(2) . . ? C12 C10 C13 110.4(2) . . ? C11 C10 C13 110.8(2) . . ? 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 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 S1 O3 115.51(11) . . ? O2 S1 O1 114.11(11) . . ? O3 S1 O1 115.10(11) . . ? O2 S1 C1 103.72(12) . . ? O3 S1 C1 103.05(12) . . ? O1 S1 C1 102.99(12) . . ? F3 C1 F1 107.9(2) . . ? F3 C1 F2 107.8(2) . . ? F1 C1 F2 107.0(2) . . ? F3 C1 S1 111.52(19) . . ? F1 C1 S1 111.38(18) . . ? F2 C1 S1 111.03(19) . . ? Cl2S C1S Cl1S 110.21(17) . . ? Cl2S C1S H1S1 109.6 . . ? Cl1S C1S H1S1 109.6 . . ? Cl2S C1S H1S2 109.6 . . ? Cl1S C1S H1S2 109.6 . . ? H1S1 C1S H1S2 108.1 . . ? 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 N5 Sb1 N2 C3 -0.80(16) . . . . ? N5 Sb1 N2 C6 178.94(18) . . . . ? C6 N2 C3 C4 -178.8(2) . . . . ? Sb1 N2 C3 C4 1.0(3) . . . . ? N2 C3 C4 N5 -0.5(3) . . . . ? C3 C4 N5 C10 178.3(2) . . . . ? C3 C4 N5 Sb1 -0.2(3) . . . . ? N2 Sb1 N5 C4 0.52(17) . . . . ? N2 Sb1 N5 C10 -177.83(19) . . . . ? C3 N2 C6 C9 66.6(3) . . . . ? Sb1 N2 C6 C9 -113.09(19) . . . . ? C3 N2 C6 C8 -173.9(2) . . . . ? Sb1 N2 C6 C8 6.4(3) . . . . ? C3 N2 C6 C7 -54.7(3) . . . . ? Sb1 N2 C6 C7 125.60(19) . . . . ? C4 N5 C10 C12 180.0(2) . . . . ? Sb1 N5 C10 C12 -1.8(3) . . . . ? C4 N5 C10 C11 -60.4(3) . . . . ? Sb1 N5 C10 C11 117.8(2) . . . . ? C4 N5 C10 C13 60.2(3) . . . . ? Sb1 N5 C10 C13 -121.5(2) . . . . ? O2 S1 C1 F3 -57.3(2) . . . . ? O3 S1 C1 F3 63.4(2) . . . . ? O1 S1 C1 F3 -176.53(19) . . . . ? O2 S1 C1 F1 63.3(2) . . . . ? O3 S1 C1 F1 -175.96(19) . . . . ? O1 S1 C1 F1 -55.9(2) . . . . ? O2 S1 C1 F2 -177.59(18) . . . . ? O3 S1 C1 F2 -56.8(2) . . . . ? O1 S1 C1 F2 63.2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1S H1S1 O2 0.99 2.32 3.193(4) 147.1 . C4 H4 Cl1S 0.95 2.99 3.916(3) 166.4 2_746 C11 H11A Cl1S 0.98 2.89 3.830(3) 160.5 2_746 C9 H9B F2 0.98 2.68 3.528(3) 144.5 1_655 C11 H11B F2 0.98 2.74 3.619(3) 149.2 3_666 C13 H13B F3 0.98 2.76 3.617(4) 146.8 2_646 C8 H8A O1 0.98 2.47 3.377(3) 154.2 3_666 C9 H9A O1 0.98 2.75 3.588(3) 144.3 3_666 C12 H12B O2 0.98 2.62 3.573(3) 165.4 2_646 C3 H3 O3 0.95 2.46 3.279(3) 144.7 1_655 C11 H11C O3 0.98 2.56 3.481(3) 157.2 2_646 C1S H1S2 O3 0.99 2.51 3.472(4) 164.1 2_656 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.304 _refine_diff_density_min -0.861 _refine_diff_density_rms 0.075 #============================================================================== #_eof # End of Crystallographic Information File