Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 loop_ _publ_author_name C.Silvestru 'Hans J. Breunig' 'Enno Lork' 'Laura M. Opris' 'Anca Silvestru' _publ_contact_author_name 'Prof Cristian Silvestru' _publ_contact_author_address ; Faculty of Chemistry & Chemical Engineering Univesitatea Babes-Bolyai Cluj-Napoca RO-3400 ROMANIA ; _publ_contact_author_email CRISTI@CHEM.UBBCLUJ.RO _publ_section_title ; Solid state structure and solution behaviour of hypervalent organoantimony halides containing 2-(Me2NCH2)C6H4- moieties ; data_laura _database_code_CSD 210849 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H24 I N2 Sb' _chemical_formula_weight 517.04 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' Sb Sb -0.5866 1.5461 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 9.6477(17) _cell_length_b 16.244(3) _cell_length_c 12.623(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.399(3) _cell_angle_gamma 90.00 _cell_volume 1978.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 6389 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.76 _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.736 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 2.954 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.312 _exptl_absorpt_correction_T_max 0.478 _exptl_absorpt_process_details '(SADABS; Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11348 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.39 _reflns_number_total 4031 _reflns_number_gt 3773 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0225P)^2^+2.8251P] 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_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4031 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0685 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 Sb1 Sb 0.90540(2) 0.146220(14) 0.557462(19) 0.04151(9) Uani 1 1 d . . . I1 I 0.73315(3) 0.087792(17) 0.74065(2) 0.06003(10) Uani 1 1 d . . . N1 N 1.0231(3) 0.17608(18) 0.3935(2) 0.0461(7) Uani 1 1 d . . . N2 N 1.0222(4) 0.3282(2) 0.6016(3) 0.0550(8) Uani 1 1 d . . . C1 C 0.8195(4) 0.0582(2) 0.4466(3) 0.0452(8) Uani 1 1 d . . . C2 C 0.8952(4) 0.0486(2) 0.3542(3) 0.0493(9) Uani 1 1 d . . . C3 C 0.8518(5) -0.0061(3) 0.2764(4) 0.0644(11) Uani 1 1 d . . . H3 H 0.9031 -0.0120 0.2148 0.077 Uiso 1 1 calc R . . C4 C 0.7326(5) -0.0519(3) 0.2903(4) 0.0724(13) Uani 1 1 d . . . H4 H 0.7033 -0.0882 0.2378 0.087 Uiso 1 1 calc R . . C5 C 0.6577(5) -0.0437(3) 0.3814(4) 0.0728(13) Uani 1 1 d . . . H5 H 0.5779 -0.0749 0.3909 0.087 Uiso 1 1 calc R . . C6 C 0.7004(4) 0.0110(3) 0.4598(4) 0.0594(10) Uani 1 1 d . . . H6 H 0.6490 0.0161 0.5215 0.071 Uiso 1 1 calc R . . C7 C 1.0305(5) 0.0942(3) 0.3438(4) 0.0595(11) Uani 1 1 d . . . H7A H 1.1039 0.0625 0.3773 0.071 Uiso 1 1 calc R . . H7B H 1.0528 0.1002 0.2694 0.071 Uiso 1 1 calc R . . C8 C 0.9511(5) 0.2352(3) 0.3239(3) 0.0599(11) Uani 1 1 d . . . H8A H 1.0011 0.2406 0.2587 0.090 Uiso 1 1 calc R . . H8B H 0.9462 0.2877 0.3584 0.090 Uiso 1 1 calc R . . H8C H 0.8590 0.2157 0.3091 0.090 Uiso 1 1 calc R . . C9 C 1.1653(4) 0.2055(3) 0.4170(4) 0.0642(11) Uani 1 1 d . . . H9A H 1.2102 0.1677 0.4646 0.096 Uiso 1 1 calc R . . H9B H 1.1609 0.2589 0.4493 0.096 Uiso 1 1 calc R . . H9C H 1.2170 0.2088 0.3525 0.096 Uiso 1 1 calc R . . C10 C 0.7522(4) 0.2416(2) 0.5317(3) 0.0441(8) Uani 1 1 d . . . C11 C 0.7703(4) 0.3172(2) 0.5837(3) 0.0504(9) Uani 1 1 d . . . C12 C 0.6740(5) 0.3796(3) 0.5657(4) 0.0625(11) Uani 1 1 d . . . H12 H 0.6856 0.4300 0.5995 0.075 Uiso 1 1 calc R . . C13 C 0.5623(5) 0.3684(3) 0.4993(4) 0.0718(13) Uani 1 1 d . . . H13 H 0.5000 0.4112 0.4873 0.086 Uiso 1 1 calc R . . C14 C 0.5432(5) 0.2936(3) 0.4507(4) 0.0689(12) Uani 1 1 d . . . H14 H 0.4666 0.2853 0.4069 0.083 Uiso 1 1 calc R . . C15 C 0.6376(4) 0.2304(3) 0.4666(3) 0.0549(10) Uani 1 1 d . . . H15 H 0.6238 0.1799 0.4333 0.066 Uiso 1 1 calc R . . C16 C 0.8911(5) 0.3293(2) 0.6572(3) 0.0583(11) Uani 1 1 d . . . H16A H 0.8812 0.3815 0.6936 0.070 Uiso 1 1 calc R . . H16B H 0.8912 0.2860 0.7101 0.070 Uiso 1 1 calc R . . C17 C 1.1389(6) 0.3168(4) 0.6744(4) 0.0825(15) Uani 1 1 d . . . H17A H 1.2234 0.3140 0.6349 0.124 Uiso 1 1 calc R . . H17B H 1.1266 0.2666 0.7134 0.124 Uiso 1 1 calc R . . H17C H 1.1433 0.3624 0.7228 0.124 Uiso 1 1 calc R . . C18 C 1.0401(6) 0.4043(3) 0.5418(4) 0.0806(15) Uani 1 1 d . . . H18A H 1.0562 0.4491 0.5900 0.121 Uiso 1 1 calc R . . H18B H 0.9580 0.4151 0.5007 0.121 Uiso 1 1 calc R . . H18C H 1.1179 0.3988 0.4954 0.121 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 Sb1 0.04258(14) 0.03803(13) 0.04386(14) 0.00082(10) -0.00354(10) 0.00179(9) I1 0.07040(19) 0.05312(17) 0.05677(18) 0.00153(12) 0.01545(13) 0.00564(13) N1 0.0466(17) 0.0414(16) 0.0502(18) 0.0050(14) 0.0032(14) 0.0034(13) N2 0.069(2) 0.0495(18) 0.0464(18) 0.0048(15) -0.0088(16) -0.0114(16) C1 0.046(2) 0.0386(18) 0.051(2) -0.0031(16) -0.0018(16) 0.0055(15) C2 0.057(2) 0.0390(19) 0.052(2) -0.0009(17) -0.0006(18) 0.0091(16) C3 0.083(3) 0.056(2) 0.054(2) -0.011(2) -0.003(2) 0.013(2) C4 0.086(3) 0.058(3) 0.073(3) -0.021(2) -0.023(3) 0.006(2) C5 0.059(3) 0.059(3) 0.100(4) -0.015(3) -0.012(3) -0.007(2) C6 0.051(2) 0.057(2) 0.070(3) -0.011(2) 0.002(2) -0.0052(19) C7 0.066(3) 0.055(2) 0.058(3) -0.002(2) 0.019(2) 0.006(2) C8 0.064(3) 0.059(2) 0.057(2) 0.015(2) 0.000(2) 0.005(2) C9 0.046(2) 0.071(3) 0.076(3) 0.008(2) 0.005(2) -0.004(2) C10 0.048(2) 0.0424(19) 0.0416(19) -0.0007(15) 0.0031(16) 0.0062(15) C11 0.067(2) 0.044(2) 0.041(2) 0.0025(16) 0.0027(18) 0.0030(18) C12 0.083(3) 0.046(2) 0.059(3) -0.003(2) 0.010(2) 0.013(2) C13 0.075(3) 0.068(3) 0.072(3) 0.006(2) 0.005(3) 0.033(2) C14 0.054(2) 0.084(3) 0.068(3) -0.003(3) -0.009(2) 0.020(2) C15 0.049(2) 0.056(2) 0.059(2) -0.0068(19) -0.0033(18) 0.0083(18) C16 0.089(3) 0.041(2) 0.045(2) -0.0041(17) -0.005(2) -0.005(2) C17 0.083(3) 0.094(4) 0.070(3) 0.001(3) -0.024(3) -0.022(3) C18 0.111(4) 0.063(3) 0.068(3) 0.014(2) -0.002(3) -0.029(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 C1 2.162(4) . ? Sb1 C10 2.165(4) . ? Sb1 N1 2.417(3) . ? Sb1 I1 3.0105(5) . ? N1 C8 1.472(5) . ? N1 C7 1.473(5) . ? N1 C9 1.481(5) . ? N2 C16 1.451(6) . ? N2 C18 1.459(5) . ? N2 C17 1.459(6) . ? C1 C2 1.389(5) . ? C1 C6 1.392(5) . ? C2 C3 1.387(6) . ? C2 C7 1.507(6) . ? C3 C4 1.382(7) . ? C4 C5 1.368(7) . ? C5 C6 1.391(6) . ? C10 C15 1.386(5) . ? C10 C11 1.403(5) . ? C11 C12 1.392(6) . ? C11 C16 1.497(6) . ? C12 C13 1.373(7) . ? C13 C14 1.372(7) . ? C14 C15 1.387(6) . ? 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 C1 Sb1 C10 96.78(14) . . ? C1 Sb1 N1 76.03(13) . . ? C10 Sb1 N1 92.99(12) . . ? C1 Sb1 I1 94.45(10) . . ? C10 Sb1 I1 87.76(10) . . ? N1 Sb1 I1 170.47(8) . . ? C8 N1 C7 111.1(3) . . ? C8 N1 C9 110.0(3) . . ? C7 N1 C9 109.2(3) . . ? C8 N1 Sb1 114.8(2) . . ? C7 N1 Sb1 102.0(2) . . ? C9 N1 Sb1 109.4(2) . . ? C16 N2 C18 110.3(4) . . ? C16 N2 C17 111.6(4) . . ? C18 N2 C17 109.9(4) . . ? C2 C1 C6 118.6(4) . . ? C2 C1 Sb1 114.6(3) . . ? C6 C1 Sb1 126.9(3) . . ? C3 C2 C1 120.5(4) . . ? C3 C2 C7 120.7(4) . . ? C1 C2 C7 118.6(4) . . ? C4 C3 C2 120.1(4) . . ? C5 C4 C3 120.0(4) . . ? C4 C5 C6 120.2(5) . . ? C5 C6 C1 120.5(4) . . ? N1 C7 C2 111.2(3) . . ? C15 C10 C11 119.3(3) . . ? C15 C10 Sb1 122.4(3) . . ? C11 C10 Sb1 118.3(3) . . ? C12 C11 C10 118.6(4) . . ? C12 C11 C16 121.5(4) . . ? C10 C11 C16 119.9(4) . . ? C13 C12 C11 121.6(4) . . ? C14 C13 C12 119.5(4) . . ? C13 C14 C15 120.4(4) . . ? C10 C15 C14 120.6(4) . . ? N2 C16 C11 112.1(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 C1 Sb1 N1 C8 88.0(3) . . . . ? C10 Sb1 N1 C8 -8.3(3) . . . . ? C1 Sb1 N1 C7 -32.2(2) . . . . ? C10 Sb1 N1 C7 -128.4(3) . . . . ? C1 Sb1 N1 C9 -147.8(3) . . . . ? C10 Sb1 N1 C9 116.0(3) . . . . ? C10 Sb1 C1 C2 107.2(3) . . . . ? N1 Sb1 C1 C2 15.8(3) . . . . ? I1 Sb1 C1 C2 -164.5(3) . . . . ? C10 Sb1 C1 C6 -73.8(4) . . . . ? N1 Sb1 C1 C6 -165.2(4) . . . . ? I1 Sb1 C1 C6 14.5(3) . . . . ? C6 C1 C2 C3 0.7(6) . . . . ? Sb1 C1 C2 C3 179.8(3) . . . . ? C6 C1 C2 C7 -174.8(4) . . . . ? Sb1 C1 C2 C7 4.2(4) . . . . ? C1 C2 C3 C4 -0.1(6) . . . . ? C7 C2 C3 C4 175.4(4) . . . . ? C2 C3 C4 C5 -0.5(7) . . . . ? C3 C4 C5 C6 0.5(8) . . . . ? C4 C5 C6 C1 0.1(7) . . . . ? C2 C1 C6 C5 -0.7(6) . . . . ? Sb1 C1 C6 C5 -179.7(3) . . . . ? C8 N1 C7 C2 -79.2(4) . . . . ? C9 N1 C7 C2 159.3(4) . . . . ? Sb1 N1 C7 C2 43.6(4) . . . . ? C3 C2 C7 N1 148.1(4) . . . . ? C1 C2 C7 N1 -36.4(5) . . . . ? C1 Sb1 C10 C15 4.7(3) . . . . ? N1 Sb1 C10 C15 81.0(3) . . . . ? I1 Sb1 C10 C15 -89.5(3) . . . . ? C1 Sb1 C10 C11 -175.6(3) . . . . ? N1 Sb1 C10 C11 -99.3(3) . . . . ? I1 Sb1 C10 C11 90.2(3) . . . . ? C15 C10 C11 C12 -1.8(6) . . . . ? Sb1 C10 C11 C12 178.5(3) . . . . ? C15 C10 C11 C16 177.9(4) . . . . ? Sb1 C10 C11 C16 -1.7(5) . . . . ? C10 C11 C12 C13 0.4(6) . . . . ? C16 C11 C12 C13 -179.3(4) . . . . ? C11 C12 C13 C14 1.2(7) . . . . ? C12 C13 C14 C15 -1.4(8) . . . . ? C11 C10 C15 C14 1.6(6) . . . . ? Sb1 C10 C15 C14 -178.8(3) . . . . ? C13 C14 C15 C10 0.1(7) . . . . ? C18 N2 C16 C11 73.5(4) . . . . ? C17 N2 C16 C11 -164.0(4) . . . . ? C12 C11 C16 N2 -113.6(4) . . . . ? C10 C11 C16 N2 66.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.562 _refine_diff_density_min -0.840 _refine_diff_density_rms 0.075 data_54richy _database_code_CSD 210850 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H37 I3 N3 O Sb' _chemical_formula_weight 922.05 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' Sb Sb -0.5866 1.5461 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/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 16.3570(10) _cell_length_b 14.1663(9) _cell_length_c 14.0075(9) _cell_angle_alpha 90.00 _cell_angle_beta 91.0300(10) _cell_angle_gamma 90.00 _cell_volume 3245.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 5893 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 22.94 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.887 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1752 _exptl_absorpt_coefficient_mu 3.727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.307 _exptl_absorpt_correction_T_max 0.572 _exptl_absorpt_process_details '(SADABS; Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25666 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 26.37 _reflns_number_total 6617 _reflns_number_gt 5527 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0310P)^2^+6.6582P] 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 6617 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.0957 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _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 Sb1 Sb 0.75358(2) 0.36237(2) 0.68099(2) 0.03581(10) Uani 1 1 d . . . I2 I 0.73232(3) 0.81212(3) 0.65121(3) 0.05668(13) Uani 1 1 d . . . I1 I 0.90506(3) 0.74843(4) 0.63728(4) 0.08023(17) Uani 1 1 d . . . I3 I 0.56357(3) 0.85946(5) 0.66710(4) 0.0931(2) Uani 1 1 d . . . N1 N 0.8984(3) 0.3606(3) 0.5946(3) 0.0494(11) Uani 1 1 d . . . N2 N 0.6339(3) 0.5339(3) 0.8055(3) 0.0513(12) Uani 1 1 d . . . N3 N 0.6464(3) 0.2649(4) 0.5598(3) 0.0559(13) Uani 1 1 d . . . O1 O 0.6524(2) 0.3469(3) 0.7479(3) 0.0491(10) Uani 1 1 d . . . C1 C 0.8025(3) 0.2257(3) 0.6975(3) 0.0397(12) Uani 1 1 d . . . C2 C 0.8819(4) 0.2049(4) 0.6711(4) 0.0480(13) Uani 1 1 d . . . C3 C 0.9105(4) 0.1125(5) 0.6871(5) 0.0636(17) Uani 1 1 d . . . H3 H 0.9633 0.0963 0.6698 0.076 Uiso 1 1 calc R . . C4 C 0.8613(6) 0.0461(5) 0.7278(5) 0.078(2) Uani 1 1 d . . . H4 H 0.8810 -0.0147 0.7377 0.094 Uiso 1 1 calc R . . C5 C 0.7838(5) 0.0683(5) 0.7539(5) 0.073(2) Uani 1 1 d . . . H5 H 0.7510 0.0224 0.7812 0.087 Uiso 1 1 calc R . . C6 C 0.7536(4) 0.1582(4) 0.7402(4) 0.0526(15) Uani 1 1 d . . . H6 H 0.7011 0.1735 0.7594 0.063 Uiso 1 1 calc R . . C7 C 0.9400(4) 0.2787(5) 0.6378(5) 0.0590(16) Uani 1 1 d . . . H7A H 0.9734 0.2999 0.6916 0.071 Uiso 1 1 calc R . . H7B H 0.9762 0.2511 0.5913 0.071 Uiso 1 1 calc R . . C8 C 0.8842(4) 0.3433(6) 0.4928(4) 0.073(2) Uani 1 1 d . . . H8A H 0.9357 0.3358 0.4619 0.110 Uiso 1 1 calc R . . H8B H 0.8553 0.3958 0.4650 0.110 Uiso 1 1 calc R . . H8C H 0.8523 0.2869 0.4846 0.110 Uiso 1 1 calc R . . C9 C 0.9529(4) 0.4436(5) 0.6069(6) 0.076(2) Uani 1 1 d . . . H9A H 1.0066 0.4280 0.5851 0.114 Uiso 1 1 calc R . . H9B H 0.9560 0.4607 0.6731 0.114 Uiso 1 1 calc R . . H9C H 0.9315 0.4956 0.5703 0.114 Uiso 1 1 calc R . . C10 C 0.8121(3) 0.4407(4) 0.7940(3) 0.0388(11) Uani 1 1 d . . . C11 C 0.7845(3) 0.5271(4) 0.8280(4) 0.0439(13) Uani 1 1 d . . . C12 C 0.8233(4) 0.5648(4) 0.9094(4) 0.0568(16) Uani 1 1 d . . . H12 H 0.8070 0.6235 0.9318 0.068 Uiso 1 1 calc R . . C13 C 0.8850(4) 0.5171(5) 0.9572(5) 0.0662(18) Uani 1 1 d . . . H13 H 0.9092 0.5430 1.0119 0.079 Uiso 1 1 calc R . . C14 C 0.9105(4) 0.4319(5) 0.9240(4) 0.0586(16) Uani 1 1 d . . . H14 H 0.9521 0.3994 0.9560 0.070 Uiso 1 1 calc R . . C15 C 0.8748(3) 0.3936(4) 0.8428(4) 0.0457(13) Uani 1 1 d . . . H15 H 0.8927 0.3355 0.8204 0.055 Uiso 1 1 calc R . . C16 C 0.7125(4) 0.5798(4) 0.7858(4) 0.0503(14) Uani 1 1 d . . . H16A H 0.7120 0.6433 0.8115 0.060 Uiso 1 1 calc R . . H16B H 0.7189 0.5845 0.7172 0.060 Uiso 1 1 calc R . . C17 C 0.6146(4) 0.5429(5) 0.9071(5) 0.0679(18) Uani 1 1 d . . . H17A H 0.6122 0.6085 0.9240 0.102 Uiso 1 1 calc R . . H17B H 0.6563 0.5122 0.9449 0.102 Uiso 1 1 calc R . . H17C H 0.5628 0.5138 0.9187 0.102 Uiso 1 1 calc R . . C18 C 0.5694(5) 0.5783(5) 0.7471(5) 0.079(2) Uani 1 1 d . . . H18A H 0.5653 0.6439 0.7635 0.118 Uiso 1 1 calc R . . H18B H 0.5182 0.5476 0.7586 0.118 Uiso 1 1 calc R . . H18C H 0.5824 0.5725 0.6808 0.118 Uiso 1 1 calc R . . C19 C 0.7173(3) 0.4520(4) 0.5666(4) 0.0441(13) Uani 1 1 d . . . C20 C 0.6455(4) 0.4326(5) 0.5158(4) 0.0561(16) Uani 1 1 d . . . C21 C 0.6206(5) 0.4982(6) 0.4467(5) 0.078(2) Uani 1 1 d . . . H21 H 0.5733 0.4864 0.4108 0.094 Uiso 1 1 calc R . . C22 C 0.6633(6) 0.5791(6) 0.4304(5) 0.082(2) Uani 1 1 d . . . H22 H 0.6447 0.6217 0.3844 0.098 Uiso 1 1 calc R . . C23 C 0.7335(5) 0.5978(5) 0.4814(4) 0.068(2) Uani 1 1 d . . . H23 H 0.7629 0.6527 0.4701 0.082 Uiso 1 1 calc R . . C24 C 0.7601(4) 0.5342(4) 0.5501(4) 0.0513(14) Uani 1 1 d . . . H24 H 0.8074 0.5470 0.5856 0.062 Uiso 1 1 calc R . . C25 C 0.5955(4) 0.3460(6) 0.5364(5) 0.071(2) Uani 1 1 d . . . H25A H 0.5598 0.3591 0.5893 0.085 Uiso 1 1 calc R . . H25B H 0.5615 0.3313 0.4809 0.085 Uiso 1 1 calc R . . C26 C 0.6850(5) 0.2272(6) 0.4731(5) 0.080(2) Uani 1 1 d . . . H26A H 0.6439 0.1993 0.4322 0.120 Uiso 1 1 calc R . . H26B H 0.7248 0.1802 0.4909 0.120 Uiso 1 1 calc R . . H26C H 0.7114 0.2776 0.4397 0.120 Uiso 1 1 calc R . . C27 C 0.5948(5) 0.1897(6) 0.6010(5) 0.087(2) Uani 1 1 d . . . H27A H 0.5495 0.1769 0.5585 0.130 Uiso 1 1 calc R . . H27B H 0.5748 0.2101 0.6616 0.130 Uiso 1 1 calc R . . H27C H 0.6268 0.1334 0.6095 0.130 Uiso 1 1 calc R . . H1 H 0.645(3) 0.394(4) 0.773(4) 0.042(18) Uiso 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 0.04084(19) 0.03609(18) 0.03059(17) -0.00057(14) 0.00317(13) -0.00373(15) I2 0.0709(3) 0.0468(2) 0.0524(2) 0.00218(18) 0.00206(19) -0.0040(2) I1 0.0548(3) 0.0738(3) 0.1119(4) 0.0027(3) -0.0040(3) -0.0077(2) I3 0.0792(4) 0.1221(5) 0.0780(4) 0.0013(3) 0.0002(3) 0.0314(3) N1 0.046(3) 0.055(3) 0.047(3) 0.005(2) 0.011(2) 0.000(2) N2 0.054(3) 0.053(3) 0.047(3) -0.003(2) -0.002(2) 0.014(2) N3 0.058(3) 0.065(3) 0.044(3) -0.010(2) 0.000(2) -0.016(3) O1 0.048(2) 0.052(3) 0.048(2) -0.010(2) 0.0109(18) -0.008(2) C1 0.055(3) 0.033(3) 0.032(3) -0.005(2) 0.000(2) -0.005(2) C2 0.058(4) 0.046(3) 0.040(3) -0.001(2) 0.002(3) 0.007(3) C3 0.075(5) 0.054(4) 0.061(4) -0.006(3) 0.004(3) 0.017(3) C4 0.121(7) 0.043(4) 0.070(5) -0.001(3) -0.013(5) 0.014(4) C5 0.107(6) 0.040(3) 0.071(5) 0.004(3) 0.013(4) -0.011(4) C6 0.069(4) 0.042(3) 0.047(3) -0.005(3) 0.008(3) -0.006(3) C7 0.050(4) 0.068(4) 0.060(4) 0.005(3) 0.010(3) 0.011(3) C8 0.068(4) 0.104(6) 0.048(4) 0.002(4) 0.018(3) 0.024(4) C9 0.056(4) 0.077(5) 0.095(5) 0.003(4) 0.016(4) -0.020(4) C10 0.040(3) 0.041(3) 0.035(3) -0.003(2) 0.004(2) -0.004(2) C11 0.053(3) 0.043(3) 0.036(3) -0.002(2) 0.004(2) -0.006(3) C12 0.066(4) 0.050(3) 0.055(4) -0.017(3) 0.002(3) -0.006(3) C13 0.073(4) 0.076(5) 0.049(4) -0.018(3) -0.010(3) -0.012(4) C14 0.051(4) 0.073(4) 0.051(4) -0.006(3) -0.014(3) -0.001(3) C15 0.043(3) 0.049(3) 0.045(3) -0.004(3) -0.002(2) 0.004(3) C16 0.067(4) 0.043(3) 0.041(3) -0.003(2) 0.005(3) 0.008(3) C17 0.075(5) 0.072(4) 0.057(4) -0.006(3) 0.015(3) 0.007(4) C18 0.076(5) 0.085(5) 0.075(5) 0.005(4) -0.006(4) 0.023(4) C19 0.051(3) 0.049(3) 0.032(3) 0.002(2) -0.002(2) 0.002(3) C20 0.053(4) 0.073(4) 0.042(3) -0.011(3) -0.008(3) 0.006(3) C21 0.085(5) 0.100(6) 0.049(4) -0.006(4) -0.023(4) 0.025(5) C22 0.127(7) 0.069(5) 0.048(4) 0.005(4) -0.016(4) 0.032(5) C23 0.117(6) 0.049(4) 0.039(3) 0.005(3) 0.010(4) 0.010(4) C24 0.068(4) 0.050(3) 0.036(3) 0.000(3) 0.003(3) 0.003(3) C25 0.052(4) 0.101(6) 0.060(4) -0.018(4) -0.010(3) -0.004(4) C26 0.096(6) 0.089(5) 0.056(4) -0.030(4) 0.013(4) -0.026(4) C27 0.093(6) 0.096(6) 0.072(5) -0.013(4) -0.002(4) -0.050(5) _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 O1 1.930(4) . ? Sb1 C1 2.106(5) . ? Sb1 C19 2.121(5) . ? Sb1 C10 2.145(5) . ? I2 I3 2.8531(7) . ? I2 I1 2.9758(7) . ? N1 C8 1.461(8) . ? N1 C7 1.471(7) . ? N1 C9 1.484(8) . ? N2 C18 1.466(8) . ? N2 C17 1.469(7) . ? N2 C16 1.471(7) . ? N3 C25 1.453(9) . ? N3 C26 1.480(8) . ? N3 C27 1.482(8) . ? C1 C2 1.389(8) . ? C1 C6 1.389(7) . ? C2 C3 1.406(8) . ? C2 C7 1.494(8) . ? C3 C4 1.368(10) . ? C4 C5 1.363(10) . ? C5 C6 1.378(9) . ? C10 C11 1.392(7) . ? C10 C15 1.392(7) . ? C11 C12 1.401(8) . ? C11 C16 1.505(8) . ? C12 C13 1.378(9) . ? C13 C14 1.363(9) . ? C14 C15 1.381(8) . ? C19 C24 1.381(8) . ? C19 C20 1.389(8) . ? C20 C21 1.397(9) . ? C20 C25 1.505(9) . ? C21 C22 1.364(11) . ? C22 C23 1.367(10) . ? C23 C24 1.382(8) . ? 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 Sb1 C1 99.8(2) . . ? O1 Sb1 C19 101.8(2) . . ? C1 Sb1 C19 137.20(19) . . ? O1 Sb1 C10 94.38(18) . . ? C1 Sb1 C10 103.36(19) . . ? C19 Sb1 C10 111.3(2) . . ? I3 I2 I1 175.90(2) . . ? C8 N1 C7 109.5(5) . . ? C8 N1 C9 109.3(5) . . ? C7 N1 C9 107.7(5) . . ? C18 N2 C17 109.8(5) . . ? C18 N2 C16 109.2(5) . . ? C17 N2 C16 110.3(5) . . ? C25 N3 C26 110.6(5) . . ? C25 N3 C27 109.2(6) . . ? C26 N3 C27 108.3(5) . . ? C2 C1 C6 121.1(5) . . ? C2 C1 Sb1 121.4(4) . . ? C6 C1 Sb1 117.4(4) . . ? C1 C2 C3 117.7(6) . . ? C1 C2 C7 122.5(5) . . ? C3 C2 C7 119.4(6) . . ? C4 C3 C2 120.7(7) . . ? C5 C4 C3 120.7(6) . . ? C4 C5 C6 120.6(7) . . ? C5 C6 C1 119.2(6) . . ? N1 C7 C2 112.9(5) . . ? C11 C10 C15 119.7(5) . . ? C11 C10 Sb1 124.3(4) . . ? C15 C10 Sb1 115.4(4) . . ? C10 C11 C12 117.9(5) . . ? C10 C11 C16 123.9(5) . . ? C12 C11 C16 118.1(5) . . ? C13 C12 C11 121.8(6) . . ? C14 C13 C12 119.6(6) . . ? C13 C14 C15 120.2(6) . . ? C14 C15 C10 120.8(5) . . ? N2 C16 C11 112.8(5) . . ? C24 C19 C20 120.5(5) . . ? C24 C19 Sb1 119.7(4) . . ? C20 C19 Sb1 119.4(4) . . ? C19 C20 C21 117.2(6) . . ? C19 C20 C25 121.3(6) . . ? C21 C20 C25 121.4(6) . . ? C22 C21 C20 122.0(7) . . ? C21 C22 C23 120.2(7) . . ? C22 C23 C24 119.3(7) . . ? C19 C24 C23 120.8(6) . . ? N3 C25 C20 112.1(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 O1 Sb1 C1 C2 -171.4(4) . . . . ? C19 Sb1 C1 C2 69.2(5) . . . . ? C10 Sb1 C1 C2 -74.5(4) . . . . ? O1 Sb1 C1 C6 5.5(4) . . . . ? C19 Sb1 C1 C6 -113.9(4) . . . . ? C10 Sb1 C1 C6 102.4(4) . . . . ? C6 C1 C2 C3 1.5(8) . . . . ? Sb1 C1 C2 C3 178.3(4) . . . . ? C6 C1 C2 C7 -171.2(5) . . . . ? Sb1 C1 C2 C7 5.5(7) . . . . ? C1 C2 C3 C4 -0.4(9) . . . . ? C7 C2 C3 C4 172.6(6) . . . . ? C2 C3 C4 C5 -0.2(11) . . . . ? C3 C4 C5 C6 -0.3(11) . . . . ? C4 C5 C6 C1 1.4(10) . . . . ? C2 C1 C6 C5 -2.0(8) . . . . ? Sb1 C1 C6 C5 -178.9(5) . . . . ? C8 N1 C7 C2 -87.8(6) . . . . ? C9 N1 C7 C2 153.4(5) . . . . ? C1 C2 C7 N1 -26.4(8) . . . . ? C3 C2 C7 N1 161.0(5) . . . . ? O1 Sb1 C10 C11 -61.2(5) . . . . ? C1 Sb1 C10 C11 -162.3(4) . . . . ? C19 Sb1 C10 C11 43.2(5) . . . . ? O1 Sb1 C10 C15 109.7(4) . . . . ? C1 Sb1 C10 C15 8.6(4) . . . . ? C19 Sb1 C10 C15 -145.8(4) . . . . ? C15 C10 C11 C12 2.1(8) . . . . ? Sb1 C10 C11 C12 172.7(4) . . . . ? C15 C10 C11 C16 -174.5(5) . . . . ? Sb1 C10 C11 C16 -3.9(7) . . . . ? C10 C11 C12 C13 -2.4(9) . . . . ? C16 C11 C12 C13 174.4(6) . . . . ? C11 C12 C13 C14 1.3(10) . . . . ? C12 C13 C14 C15 0.1(10) . . . . ? C13 C14 C15 C10 -0.4(9) . . . . ? C11 C10 C15 C14 -0.8(8) . . . . ? Sb1 C10 C15 C14 -172.2(5) . . . . ? C18 N2 C16 C11 -169.0(5) . . . . ? C17 N2 C16 C11 70.2(6) . . . . ? C10 C11 C16 N2 71.0(7) . . . . ? C12 C11 C16 N2 -105.5(6) . . . . ? O1 Sb1 C19 C24 127.5(4) . . . . ? C1 Sb1 C19 C24 -113.8(5) . . . . ? C10 Sb1 C19 C24 28.0(5) . . . . ? O1 Sb1 C19 C20 -45.4(5) . . . . ? C1 Sb1 C19 C20 73.3(5) . . . . ? C10 Sb1 C19 C20 -144.9(4) . . . . ? C24 C19 C20 C21 1.6(9) . . . . ? Sb1 C19 C20 C21 174.5(5) . . . . ? C24 C19 C20 C25 -176.6(6) . . . . ? Sb1 C19 C20 C25 -3.7(8) . . . . ? C19 C20 C21 C22 -1.3(10) . . . . ? C25 C20 C21 C22 176.9(7) . . . . ? C20 C21 C22 C23 0.7(12) . . . . ? C21 C22 C23 C24 -0.5(11) . . . . ? C20 C19 C24 C23 -1.4(9) . . . . ? Sb1 C19 C24 C23 -174.3(4) . . . . ? C22 C23 C24 C19 0.8(9) . . . . ? C26 N3 C25 C20 -74.1(6) . . . . ? C27 N3 C25 C20 166.8(5) . . . . ? C19 C20 C25 N3 -37.1(8) . . . . ? C21 C20 C25 N3 144.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.415 _refine_diff_density_min -0.923 _refine_diff_density_rms 0.098 data_65richy _database_code_CSD 210851 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H12 I2 N Sb' _chemical_formula_weight 509.75 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' Sb Sb -0.5866 1.5461 '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' N N 0.0061 0.0033 '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 ' 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 9.9046(9) _cell_length_b 8.4738(8) _cell_length_c 15.8002(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.721(2) _cell_angle_gamma 90.00 _cell_volume 1319.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4802 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.27 _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 6.733 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.290 _exptl_absorpt_correction_T_max 0.477 _exptl_absorpt_process_details '(SADABS; Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10228 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 26.35 _reflns_number_total 2698 _reflns_number_gt 2507 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0292P)^2^+1.0206P] 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 2698 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0681 _refine_ls_wR_factor_gt 0.0663 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_restrained_S_all 1.160 _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 Sb1 Sb 0.62538(3) 0.25272(4) 0.010102(19) 0.03805(10) Uani 1 1 d . . . I1 I 0.55333(4) 0.48576(4) -0.12973(2) 0.05239(12) Uani 1 1 d . . . I2 I 0.75043(4) 0.06283(5) -0.10583(2) 0.06036(13) Uani 1 1 d . . . C6 C 0.8296(5) 0.5349(5) 0.0475(3) 0.0425(10) Uani 1 1 d . . . H6 H 0.7686 0.5941 0.0119 0.051 Uiso 1 1 calc R . . C5 C 0.9446(5) 0.6052(6) 0.0870(3) 0.0494(12) Uani 1 1 d . . . H5 H 0.9606 0.7117 0.0781 0.059 Uiso 1 1 calc R . . C2 C 0.8980(4) 0.2892(6) 0.1142(3) 0.0412(10) Uani 1 1 d . . . C4 C 1.0361(5) 0.5183(7) 0.1398(3) 0.0549(14) Uani 1 1 d . . . H4 H 1.1137 0.5664 0.1661 0.066 Uiso 1 1 calc R . . C1 C 0.8048(4) 0.3770(5) 0.0606(3) 0.0371(9) Uani 1 1 d . . . C3 C 1.0128(5) 0.3616(6) 0.1535(3) 0.0497(12) Uani 1 1 d . . . H3 H 1.0743 0.3037 0.1894 0.060 Uiso 1 1 calc R . . N1 N 0.7249(4) 0.0861(4) 0.1230(2) 0.0443(9) Uani 1 1 d . . . C7 C 0.8729(5) 0.1161(6) 0.1266(3) 0.0484(12) Uani 1 1 d . . . H7A H 0.9111 0.0560 0.0825 0.058 Uiso 1 1 calc R . . H7B H 0.9168 0.0823 0.1812 0.058 Uiso 1 1 calc R . . C9 C 0.6714(5) 0.1435(7) 0.2014(3) 0.0561(13) Uani 1 1 d . . . H9A H 0.7066 0.0794 0.2486 0.084 Uiso 1 1 calc R . . H9B H 0.5742 0.1372 0.1949 0.084 Uiso 1 1 calc R . . H9C H 0.6987 0.2511 0.2114 0.084 Uiso 1 1 calc R . . C8 C 0.6943(7) -0.0839(6) 0.1128(4) 0.0659(16) Uani 1 1 d . . . H8A H 0.7427 -0.1417 0.1585 0.099 Uiso 1 1 calc R . . H8B H 0.7216 -0.1200 0.0595 0.099 Uiso 1 1 calc R . . H8C H 0.5986 -0.1005 0.1138 0.099 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 Sb1 0.03280(17) 0.04180(18) 0.03798(18) -0.00512(12) -0.00432(12) 0.00166(12) I1 0.0538(2) 0.0625(2) 0.03947(19) 0.00235(14) -0.00221(14) 0.01454(16) I2 0.0578(2) 0.0647(2) 0.0574(2) -0.02269(17) -0.00006(17) 0.01221(17) C6 0.043(3) 0.045(3) 0.039(3) -0.005(2) 0.006(2) 0.000(2) C5 0.049(3) 0.051(3) 0.050(3) -0.013(2) 0.016(2) -0.014(2) C2 0.035(2) 0.050(3) 0.038(2) -0.005(2) 0.0013(18) -0.001(2) C4 0.040(3) 0.077(4) 0.048(3) -0.021(3) 0.005(2) -0.017(3) C1 0.032(2) 0.045(2) 0.034(2) -0.0103(19) 0.0026(17) -0.0014(19) C3 0.036(2) 0.068(3) 0.044(3) -0.005(2) -0.002(2) -0.002(2) N1 0.048(2) 0.039(2) 0.043(2) 0.0035(17) -0.0104(18) -0.0026(17) C7 0.041(3) 0.054(3) 0.048(3) 0.000(2) -0.008(2) 0.008(2) C9 0.056(3) 0.065(3) 0.047(3) 0.009(3) 0.003(2) 0.001(3) C8 0.082(4) 0.040(3) 0.071(4) 0.008(3) -0.020(3) -0.007(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 C1 2.150(4) . ? Sb1 N1 2.408(4) . ? Sb1 I2 2.8161(5) . ? Sb1 I1 2.9960(5) . ? C6 C5 1.378(7) . ? C6 C1 1.380(6) . ? C5 C4 1.382(8) . ? C2 C3 1.383(6) . ? C2 C1 1.403(6) . ? C2 C7 1.504(7) . ? C4 C3 1.368(7) . ? N1 C9 1.477(7) . ? N1 C8 1.478(6) . ? N1 C7 1.483(6) . ? 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 C1 Sb1 N1 75.51(15) . . ? C1 Sb1 I2 96.92(11) . . ? N1 Sb1 I2 88.43(10) . . ? C1 Sb1 I1 94.49(12) . . ? N1 Sb1 I1 169.34(9) . . ? I2 Sb1 I1 89.131(15) . . ? C5 C6 C1 120.2(5) . . ? C6 C5 C4 120.4(5) . . ? C3 C2 C1 119.8(5) . . ? C3 C2 C7 120.9(4) . . ? C1 C2 C7 119.2(4) . . ? C3 C4 C5 120.1(5) . . ? C6 C1 C2 119.2(4) . . ? C6 C1 Sb1 124.9(3) . . ? C2 C1 Sb1 115.8(3) . . ? C4 C3 C2 120.2(5) . . ? C9 N1 C8 109.0(4) . . ? C9 N1 C7 110.3(4) . . ? C8 N1 C7 111.3(4) . . ? C9 N1 Sb1 105.9(3) . . ? C8 N1 Sb1 115.2(3) . . ? C7 N1 Sb1 105.0(3) . . ? N1 C7 C2 109.8(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C6 C5 C4 0.2(7) . . . . ? C6 C5 C4 C3 -0.3(8) . . . . ? C5 C6 C1 C2 -0.2(7) . . . . ? C5 C6 C1 Sb1 176.2(3) . . . . ? C3 C2 C1 C6 0.4(7) . . . . ? C7 C2 C1 C6 -178.3(4) . . . . ? C3 C2 C1 Sb1 -176.4(3) . . . . ? C7 C2 C1 Sb1 5.0(5) . . . . ? N1 Sb1 C1 C6 -162.5(4) . . . . ? I2 Sb1 C1 C6 110.9(4) . . . . ? I1 Sb1 C1 C6 21.3(4) . . . . ? N1 Sb1 C1 C2 14.0(3) . . . . ? I2 Sb1 C1 C2 -72.5(3) . . . . ? I1 Sb1 C1 C2 -162.2(3) . . . . ? C5 C4 C3 C2 0.4(8) . . . . ? C1 C2 C3 C4 -0.5(7) . . . . ? C7 C2 C3 C4 178.2(5) . . . . ? C1 Sb1 N1 C9 86.8(3) . . . . ? I2 Sb1 N1 C9 -175.6(3) . . . . ? I1 Sb1 N1 C9 107.5(6) . . . . ? C1 Sb1 N1 C8 -152.7(4) . . . . ? I2 Sb1 N1 C8 -55.1(4) . . . . ? I1 Sb1 N1 C8 -131.9(5) . . . . ? C1 Sb1 N1 C7 -29.9(3) . . . . ? I2 Sb1 N1 C7 67.6(3) . . . . ? I1 Sb1 N1 C7 -9.2(7) . . . . ? C9 N1 C7 C2 -73.4(5) . . . . ? C8 N1 C7 C2 165.5(4) . . . . ? Sb1 N1 C7 C2 40.2(4) . . . . ? C3 C2 C7 N1 147.9(4) . . . . ? C1 C2 C7 N1 -33.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.516 _refine_diff_density_min -1.129 _refine_diff_density_rms 0.176 data_cs11i _database_code_CSD 211552 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 Br N2 Sb' _chemical_formula_sum 'C18 H24 Br N2 Sb' _chemical_formula_weight 470.05 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' Br Br -0.2901 2.4595 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.762(2) _cell_length_b 12.890(3) _cell_length_c 16.109(3) _cell_angle_alpha 93.11(3) _cell_angle_beta 91.45(3) _cell_angle_gamma 110.24(3) _cell_volume 1897.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 26.05 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 3.560 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.2691 _exptl_absorpt_correction_T_max 0.3301 _exptl_absorpt_process_details 'Stuart & Walker Acta Cryst. 1983' _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_type 'STOE IPDS' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'random variation +/-2.0' _diffrn_reflns_number 24429 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.05 _reflns_number_total 6851 _reflns_number_gt 5027 _reflns_threshold_expression >2\s(I) _computing_data_collection 'STOE Exposed' _computing_cell_refinement 'STOE Cell' _computing_data_reduction 'STOE Integrate' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material SHELXL-97 _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^)+(0.0313P)^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 refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6851 _refine_ls_number_parameters 408 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0227 _refine_ls_wR_factor_ref 0.0566 _refine_ls_wR_factor_gt 0.0525 _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_restrained_S_all 0.922 _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 Sb1 Sb 0.61960(2) 0.679041(15) 0.028644(11) 0.02649(6) Uani 1 1 d . . . Br1 Br 0.89416(4) 0.66006(3) 0.04087(2) 0.03895(9) Uani 1 1 d . . . N1 N 0.3839(3) 0.6943(2) 0.05522(15) 0.0315(6) Uani 1 1 d . . . N2 N 0.5810(3) 0.8105(2) -0.13380(16) 0.0391(6) Uani 1 1 d . . . Sb2 Sb 0.13302(2) 0.682488(15) -0.464484(11) 0.02610(6) Uani 1 1 d . . . Br2 Br 0.40946(4) 0.67125(3) -0.45064(2) 0.03611(8) Uani 1 1 d . . . N3 N -0.0985(3) 0.7061(2) -0.43517(15) 0.0316(6) Uani 1 1 d . . . N4 N 0.1189(3) 0.8217(2) -0.63232(16) 0.0382(6) Uani 1 1 d . . . C1 C 0.5886(3) 0.6495(2) 0.15884(17) 0.0301(6) Uani 1 1 d . . . C6 C 0.6978(4) 0.6560(3) 0.21806(18) 0.0352(7) Uani 1 1 d . . . H6 H 0.7965 0.6769 0.2027 0.042(2) Uiso 1 1 calc R . . C5 C 0.6632(4) 0.6321(3) 0.29980(19) 0.0424(8) Uani 1 1 d . . . H5 H 0.7386 0.6370 0.3399 0.042(2) Uiso 1 1 calc R . . C4 C 0.5195(4) 0.6012(3) 0.3230(2) 0.0437(8) Uani 1 1 d . . . H4 H 0.4961 0.5845 0.3788 0.042(2) Uiso 1 1 calc R . . C3 C 0.4104(4) 0.5950(3) 0.2644(2) 0.0424(8) Uani 1 1 d . . . H3 H 0.3119 0.5742 0.2802 0.042(2) Uiso 1 1 calc R . . C2 C 0.4435(3) 0.6188(2) 0.18258(18) 0.0323(7) Uani 1 1 d . . . C7 C 0.3268(3) 0.6090(3) 0.11627(19) 0.0360(7) Uani 1 1 d . . . H7A H 0.2948 0.5343 0.0873 0.036(3) Uiso 1 1 calc R . . H7B H 0.2410 0.6189 0.1424 0.036(3) Uiso 1 1 calc R . . C8 C 0.3895(4) 0.8040(3) 0.0908(2) 0.0425(8) Uani 1 1 d . . . H8A H 0.4339 0.8603 0.0515 0.052(2) Uiso 1 1 calc R . . H8B H 0.4481 0.8223 0.1433 0.052(2) Uiso 1 1 calc R . . H8C H 0.2901 0.8021 0.1010 0.052(2) Uiso 1 1 calc R . . C9 C 0.2895(4) 0.6641(3) -0.0217(2) 0.0438(8) Uani 1 1 d . . . H9A H 0.1904 0.6603 -0.0088 0.052(2) Uiso 1 1 calc R . . H9B H 0.2867 0.5918 -0.0456 0.052(2) Uiso 1 1 calc R . . H9C H 0.3288 0.7202 -0.0619 0.052(2) Uiso 1 1 calc R . . C10 C 0.7291(3) 0.8573(2) 0.04380(18) 0.0286(6) Uani 1 1 d . . . C15 C 0.7662(4) 0.9113(2) 0.12290(19) 0.0349(7) Uani 1 1 d . . . H15 H 0.7421 0.8697 0.1707 0.042(2) Uiso 1 1 calc R . . C14 C 0.8382(4) 1.0253(3) 0.1326(2) 0.0398(8) Uani 1 1 d . . . H14 H 0.8615 1.0614 0.1867 0.042(2) Uiso 1 1 calc R . . C13 C 0.8758(4) 1.0858(3) 0.0633(2) 0.0385(7) Uani 1 1 d . . . H13 H 0.9239 1.1638 0.0696 0.042(2) Uiso 1 1 calc R . . C12 C 0.8430(3) 1.0323(3) -0.0155(2) 0.0353(7) Uani 1 1 d . . . H12 H 0.8713 1.0741 -0.0629 0.042(2) Uiso 1 1 calc R . . C11 C 0.7691(3) 0.9180(2) -0.02639(18) 0.0302(6) Uani 1 1 d . . . C16 C 0.7382(3) 0.8599(3) -0.11278(19) 0.0345(7) Uani 1 1 d . . . H16A H 0.7848 0.9139 -0.1541 0.036(3) Uiso 1 1 calc R . . H16B H 0.7820 0.8011 -0.1158 0.036(3) Uiso 1 1 calc R . . C17 C 0.5169(4) 0.8951(4) -0.1472(2) 0.0569(11) Uani 1 1 d . . . H17A H 0.5638 0.9387 -0.1932 0.052(2) Uiso 1 1 calc R . . H17B H 0.5317 0.9440 -0.0964 0.052(2) Uiso 1 1 calc R . . H17C H 0.4119 0.8596 -0.1608 0.052(2) Uiso 1 1 calc R . . C18 C 0.5539(5) 0.7330(4) -0.2073(2) 0.0624(11) Uani 1 1 d . . . H18A H 0.4484 0.6992 -0.2198 0.052(2) Uiso 1 1 calc R . . H18B H 0.5942 0.6749 -0.1964 0.052(2) Uiso 1 1 calc R . . H18C H 0.6010 0.7729 -0.2549 0.052(2) Uiso 1 1 calc R . . C19 C 0.0937(3) 0.6415(2) -0.33688(17) 0.0292(6) Uani 1 1 d . . . C24 C 0.1649(3) 0.5824(3) -0.29384(18) 0.0324(7) Uani 1 1 d . . . H24 H 0.2399 0.5627 -0.3195 0.042(2) Uiso 1 1 calc R . . C23 C 0.1272(4) 0.5518(3) -0.21356(19) 0.0388(7) Uani 1 1 d . . . H23 H 0.1759 0.5109 -0.1851 0.042(2) Uiso 1 1 calc R . . C22 C 0.0200(4) 0.5806(3) -0.17529(19) 0.0403(8) Uani 1 1 d . . . H22 H -0.0045 0.5605 -0.1203 0.042(2) Uiso 1 1 calc R . . C21 C -0.0527(4) 0.6395(3) -0.21766(19) 0.0391(7) Uani 1 1 d . . . H21 H -0.1268 0.6596 -0.1914 0.042(2) Uiso 1 1 calc R . . C20 C -0.0168(3) 0.6688(3) -0.29835(18) 0.0328(7) Uani 1 1 d . . . C25 C -0.0940(4) 0.7337(3) -0.34468(19) 0.0367(7) Uani 1 1 d . . . H25A H -0.1948 0.7155 -0.3257 0.036(3) Uiso 1 1 calc R . . H25B H -0.0416 0.8141 -0.3326 0.036(3) Uiso 1 1 calc R . . C26 C -0.2104(3) 0.5967(3) -0.4581(2) 0.0385(7) Uani 1 1 d . . . H26A H -0.1921 0.5408 -0.4249 0.052(2) Uiso 1 1 calc R . . H26B H -0.2059 0.5771 -0.5173 0.052(2) Uiso 1 1 calc R . . H26C H -0.3075 0.5993 -0.4472 0.052(2) Uiso 1 1 calc R . . C27 C -0.1324(4) 0.7906(3) -0.4822(2) 0.0418(8) Uani 1 1 d . . . H27A H -0.2278 0.7931 -0.4670 0.052(2) Uiso 1 1 calc R . . H27B H -0.1348 0.7711 -0.5420 0.052(2) Uiso 1 1 calc R . . H27C H -0.0570 0.8633 -0.4687 0.052(2) Uiso 1 1 calc R . . C28 C 0.2348(3) 0.8599(2) -0.44318(18) 0.0289(6) Uani 1 1 d . . . C33 C 0.2584(4) 0.9105(3) -0.36315(19) 0.0349(7) Uani 1 1 d . . . H33 H 0.2303 0.8667 -0.3167 0.042(2) Uiso 1 1 calc R . . C32 C 0.3235(4) 1.0259(3) -0.3506(2) 0.0415(8) Uani 1 1 d . . . H32 H 0.3382 1.0603 -0.2958 0.042(2) Uiso 1 1 calc R . . C31 C 0.3663(4) 1.0896(3) -0.4181(2) 0.0410(8) Uani 1 1 d . . . H31 H 0.4078 1.1680 -0.4101 0.042(2) Uiso 1 1 calc R . . C30 C 0.3482(3) 1.0385(3) -0.4974(2) 0.0368(7) Uani 1 1 d . . . H30 H 0.3810 1.0823 -0.5434 0.042(2) Uiso 1 1 calc R . . C29 C 0.2830(3) 0.9244(2) -0.51099(18) 0.0298(6) Uani 1 1 d . . . C34 C 0.2701(3) 0.8710(3) -0.59839(19) 0.0353(7) Uani 1 1 d . . . H34A H 0.3265 0.9276 -0.6355 0.036(3) Uiso 1 1 calc R . . H34B H 0.3144 0.8126 -0.5981 0.036(3) Uiso 1 1 calc R . . C36 C 0.0618(4) 0.9084(3) -0.6549(2) 0.0555(10) Uani 1 1 d . . . H36A H 0.1195 0.9501 -0.6989 0.052(2) Uiso 1 1 calc R . . H36B H 0.0684 0.9587 -0.6059 0.052(2) Uiso 1 1 calc R . . H36C H -0.0406 0.8742 -0.6749 0.052(2) Uiso 1 1 calc R . . C35 C 0.1117(5) 0.7452(4) -0.7045(2) 0.0644(12) Uani 1 1 d . . . H35A H 0.0105 0.7128 -0.7269 0.052(2) Uiso 1 1 calc R . . H35B H 0.1458 0.6861 -0.6875 0.052(2) Uiso 1 1 calc R . . H35C H 0.1740 0.7857 -0.7474 0.052(2) 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 Sb1 0.02702(12) 0.02481(11) 0.02599(10) 0.00078(8) 0.00174(9) 0.00706(9) Br1 0.03358(19) 0.04027(19) 0.04663(18) 0.00973(15) 0.01023(16) 0.01588(15) N1 0.0227(13) 0.0342(14) 0.0351(13) 0.0055(11) 0.0007(11) 0.0061(11) N2 0.0293(15) 0.0498(17) 0.0362(13) 0.0019(12) -0.0002(12) 0.0117(13) Sb2 0.02702(12) 0.02331(11) 0.02707(10) 0.00027(8) 0.00109(9) 0.00782(9) Br2 0.02949(17) 0.03586(18) 0.04294(17) 0.00295(14) 0.00548(15) 0.01101(14) N3 0.0284(14) 0.0307(13) 0.0382(13) 0.0029(11) 0.0002(12) 0.0137(12) N4 0.0316(15) 0.0474(16) 0.0342(13) -0.0005(12) -0.0029(12) 0.0127(13) C1 0.0351(17) 0.0247(14) 0.0298(14) 0.0043(12) 0.0041(14) 0.0089(13) C6 0.0384(18) 0.0362(17) 0.0322(15) 0.0060(13) 0.0008(14) 0.0139(15) C5 0.051(2) 0.0450(19) 0.0324(16) 0.0019(14) -0.0048(16) 0.0188(17) C4 0.059(2) 0.0420(19) 0.0311(15) 0.0054(14) 0.0115(17) 0.0173(18) C3 0.047(2) 0.0369(18) 0.0409(17) 0.0066(14) 0.0130(16) 0.0108(16) C2 0.0320(17) 0.0270(15) 0.0364(15) 0.0036(12) 0.0076(14) 0.0077(13) C7 0.0287(17) 0.0356(16) 0.0409(16) 0.0078(14) 0.0066(14) 0.0064(14) C8 0.0375(19) 0.0402(18) 0.0534(19) 0.0057(15) 0.0078(16) 0.0174(16) C9 0.0304(18) 0.054(2) 0.0457(18) 0.0075(16) -0.0029(16) 0.0122(16) C10 0.0217(15) 0.0258(15) 0.0365(15) -0.0004(12) 0.0009(13) 0.0065(13) C15 0.0352(18) 0.0295(16) 0.0369(15) 0.0001(13) 0.0024(14) 0.0076(14) C14 0.0358(19) 0.0352(17) 0.0423(17) -0.0080(14) 0.0015(16) 0.0064(15) C13 0.0308(18) 0.0257(15) 0.0554(19) 0.0029(14) 0.0029(16) 0.0054(14) C12 0.0294(17) 0.0315(17) 0.0445(17) 0.0101(14) 0.0027(15) 0.0086(14) C11 0.0239(16) 0.0301(15) 0.0364(15) 0.0050(12) 0.0005(13) 0.0088(13) C16 0.0285(17) 0.0382(17) 0.0383(16) 0.0073(14) 0.0054(14) 0.0123(14) C17 0.044(2) 0.075(3) 0.056(2) 0.019(2) -0.0062(19) 0.024(2) C18 0.041(2) 0.092(3) 0.0429(19) -0.017(2) -0.0043(18) 0.012(2) C19 0.0292(16) 0.0252(14) 0.0307(14) -0.0003(12) 0.0022(13) 0.0067(13) C24 0.0300(17) 0.0343(16) 0.0310(14) 0.0041(12) 0.0001(13) 0.0086(14) C23 0.0367(19) 0.0397(18) 0.0344(15) 0.0081(14) -0.0027(15) 0.0058(15) C22 0.0347(19) 0.0447(19) 0.0303(15) 0.0038(14) 0.0019(15) -0.0007(16) C21 0.0316(18) 0.0447(19) 0.0350(16) -0.0052(14) 0.0027(14) 0.0066(15) C20 0.0276(17) 0.0335(16) 0.0336(14) -0.0026(13) 0.0012(13) 0.0069(14) C25 0.0381(18) 0.0370(17) 0.0396(16) 0.0017(13) 0.0048(14) 0.0187(15) C26 0.0298(17) 0.0358(17) 0.0478(18) 0.0017(14) -0.0012(15) 0.0089(14) C27 0.042(2) 0.0402(18) 0.0509(19) 0.0097(15) -0.0011(16) 0.0235(16) C28 0.0263(16) 0.0239(14) 0.0362(15) 0.0023(12) -0.0004(13) 0.0086(13) C33 0.0360(18) 0.0316(16) 0.0352(15) 0.0007(13) 0.0008(14) 0.0096(14) C32 0.039(2) 0.0385(18) 0.0427(17) -0.0112(15) -0.0017(16) 0.0097(16) C31 0.0321(18) 0.0246(16) 0.065(2) -0.0015(15) -0.0060(17) 0.0094(14) C30 0.0301(17) 0.0308(16) 0.0493(18) 0.0092(14) 0.0012(15) 0.0094(14) C29 0.0232(15) 0.0301(15) 0.0362(15) 0.0047(13) 0.0003(13) 0.0089(13) C34 0.0299(17) 0.0397(18) 0.0363(15) 0.0085(14) 0.0035(14) 0.0111(15) C36 0.047(2) 0.073(3) 0.053(2) 0.015(2) -0.0063(19) 0.027(2) C35 0.050(3) 0.091(3) 0.049(2) -0.025(2) -0.012(2) 0.026(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 C1 2.162(3) . ? Sb1 C10 2.169(3) . ? Sb1 N1 2.422(3) . ? Sb1 Br1 2.7776(7) . ? N1 C9 1.476(4) . ? N1 C8 1.480(4) . ? N1 C7 1.485(4) . ? N2 C17 1.456(4) . ? N2 C18 1.464(5) . ? N2 C16 1.467(4) . ? Sb2 C28 2.159(3) . ? Sb2 C19 2.161(3) . ? Sb2 N3 2.437(3) . ? Sb2 Br2 2.7562(7) . ? N3 C26 1.475(4) . ? N3 C25 1.477(4) . ? N3 C27 1.481(4) . ? N4 C34 1.467(4) . ? N4 C35 1.467(5) . ? N4 C36 1.469(4) . ? C1 C6 1.389(4) . ? C1 C2 1.402(4) . ? C6 C5 1.392(4) . ? C5 C4 1.387(5) . ? C4 C3 1.383(5) . ? C3 C2 1.390(4) . ? C2 C7 1.510(4) . ? C10 C15 1.395(4) . ? C10 C11 1.397(4) . ? C15 C14 1.390(4) . ? C14 C13 1.381(5) . ? C13 C12 1.386(5) . ? C12 C11 1.397(4) . ? C11 C16 1.516(4) . ? C19 C24 1.395(4) . ? C19 C20 1.395(4) . ? C24 C23 1.393(4) . ? C23 C22 1.374(5) . ? C22 C21 1.397(5) . ? C21 C20 1.393(4) . ? C20 C25 1.517(4) . ? C28 C33 1.389(4) . ? C28 C29 1.400(4) . ? C33 C32 1.401(4) . ? C32 C31 1.384(5) . ? C31 C30 1.383(5) . ? C30 C29 1.388(4) . ? C29 C34 1.516(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 C1 Sb1 C10 97.54(11) . . ? C1 Sb1 N1 75.08(10) . . ? C10 Sb1 N1 92.19(10) . . ? C1 Sb1 Br1 90.82(9) . . ? C10 Sb1 Br1 87.46(8) . . ? N1 Sb1 Br1 165.73(6) . . ? C9 N1 C8 109.5(3) . . ? C9 N1 C7 110.0(2) . . ? C8 N1 C7 110.3(3) . . ? C9 N1 Sb1 110.06(19) . . ? C8 N1 Sb1 115.0(2) . . ? C7 N1 Sb1 101.71(17) . . ? C17 N2 C18 110.6(3) . . ? C17 N2 C16 111.4(3) . . ? C18 N2 C16 110.4(3) . . ? C28 Sb2 C19 98.54(11) . . ? C28 Sb2 N3 87.38(10) . . ? C19 Sb2 N3 74.52(10) . . ? C28 Sb2 Br2 87.23(8) . . ? C19 Sb2 Br2 91.37(9) . . ? N3 Sb2 Br2 163.96(6) . . ? C26 N3 C25 110.7(3) . . ? C26 N3 C27 108.8(2) . . ? C25 N3 C27 110.5(2) . . ? C26 N3 Sb2 104.66(18) . . ? C25 N3 Sb2 106.44(18) . . ? C27 N3 Sb2 115.5(2) . . ? C34 N4 C35 109.9(3) . . ? C34 N4 C36 110.6(3) . . ? C35 N4 C36 110.9(3) . . ? C6 C1 C2 119.1(3) . . ? C6 C1 Sb1 125.8(2) . . ? C2 C1 Sb1 115.1(2) . . ? C1 C6 C5 120.3(3) . . ? C4 C5 C6 120.4(3) . . ? C3 C4 C5 119.5(3) . . ? C4 C3 C2 120.6(3) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 C7 122.1(3) . . ? C1 C2 C7 117.9(3) . . ? N1 C7 C2 110.3(2) . . ? C15 C10 C11 119.5(3) . . ? C15 C10 Sb1 120.8(2) . . ? C11 C10 Sb1 119.7(2) . . ? C14 C15 C10 120.8(3) . . ? C13 C14 C15 119.8(3) . . ? C14 C13 C12 119.8(3) . . ? C13 C12 C11 121.1(3) . . ? C10 C11 C12 119.0(3) . . ? C10 C11 C16 120.4(3) . . ? C12 C11 C16 120.6(3) . . ? N2 C16 C11 111.9(3) . . ? C24 C19 C20 118.8(3) . . ? C24 C19 Sb2 123.5(2) . . ? C20 C19 Sb2 117.5(2) . . ? C23 C24 C19 120.6(3) . . ? C22 C23 C24 120.4(3) . . ? C23 C22 C21 119.7(3) . . ? C20 C21 C22 120.1(3) . . ? C21 C20 C19 120.4(3) . . ? C21 C20 C25 120.6(3) . . ? C19 C20 C25 119.0(3) . . ? N3 C25 C20 110.0(2) . . ? C33 C28 C29 119.5(3) . . ? C33 C28 Sb2 121.1(2) . . ? C29 C28 Sb2 119.3(2) . . ? C28 C33 C32 120.3(3) . . ? C31 C32 C33 119.8(3) . . ? C30 C31 C32 119.6(3) . . ? C31 C30 C29 121.2(3) . . ? C30 C29 C28 119.4(3) . . ? C30 C29 C34 119.7(3) . . ? C28 C29 C34 120.9(3) . . ? N4 C34 C29 113.6(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 C1 Sb1 N1 C9 -152.1(2) . . . . ? C10 Sb1 N1 C9 110.7(2) . . . . ? Br1 Sb1 N1 C9 -161.0(2) . . . . ? C1 Sb1 N1 C8 83.7(2) . . . . ? C10 Sb1 N1 C8 -13.5(2) . . . . ? Br1 Sb1 N1 C8 74.8(3) . . . . ? C1 Sb1 N1 C7 -35.44(18) . . . . ? C10 Sb1 N1 C7 -132.66(19) . . . . ? Br1 Sb1 N1 C7 -44.4(4) . . . . ? C28 Sb2 N3 C26 170.47(19) . . . . ? C19 Sb2 N3 C26 -89.92(19) . . . . ? Br2 Sb2 N3 C26 -119.0(2) . . . . ? C28 Sb2 N3 C25 -72.21(19) . . . . ? C19 Sb2 N3 C25 27.40(19) . . . . ? Br2 Sb2 N3 C25 -1.7(3) . . . . ? C28 Sb2 N3 C27 50.8(2) . . . . ? C19 Sb2 N3 C27 150.5(2) . . . . ? Br2 Sb2 N3 C27 121.3(2) . . . . ? C10 Sb1 C1 C6 -71.6(3) . . . . ? N1 Sb1 C1 C6 -161.9(3) . . . . ? Br1 Sb1 C1 C6 15.9(3) . . . . ? C10 Sb1 C1 C2 110.0(2) . . . . ? N1 Sb1 C1 C2 19.7(2) . . . . ? Br1 Sb1 C1 C2 -162.5(2) . . . . ? C2 C1 C6 C5 0.1(5) . . . . ? Sb1 C1 C6 C5 -178.3(2) . . . . ? C1 C6 C5 C4 0.2(5) . . . . ? C6 C5 C4 C3 -0.4(5) . . . . ? C5 C4 C3 C2 0.3(5) . . . . ? C4 C3 C2 C1 0.0(5) . . . . ? C4 C3 C2 C7 177.9(3) . . . . ? C6 C1 C2 C3 -0.2(4) . . . . ? Sb1 C1 C2 C3 178.4(2) . . . . ? C6 C1 C2 C7 -178.2(3) . . . . ? Sb1 C1 C2 C7 0.4(3) . . . . ? C9 N1 C7 C2 162.5(3) . . . . ? C8 N1 C7 C2 -76.6(3) . . . . ? Sb1 N1 C7 C2 45.9(3) . . . . ? C3 C2 C7 N1 146.8(3) . . . . ? C1 C2 C7 N1 -35.3(4) . . . . ? C1 Sb1 C10 C15 5.2(3) . . . . ? N1 Sb1 C10 C15 80.4(3) . . . . ? Br1 Sb1 C10 C15 -85.3(2) . . . . ? C1 Sb1 C10 C11 -177.9(2) . . . . ? N1 Sb1 C10 C11 -102.7(2) . . . . ? Br1 Sb1 C10 C11 91.6(2) . . . . ? C11 C10 C15 C14 2.2(5) . . . . ? Sb1 C10 C15 C14 179.1(2) . . . . ? C10 C15 C14 C13 -1.1(5) . . . . ? C15 C14 C13 C12 -0.8(5) . . . . ? C14 C13 C12 C11 1.6(5) . . . . ? C15 C10 C11 C12 -1.3(4) . . . . ? Sb1 C10 C11 C12 -178.3(2) . . . . ? C15 C10 C11 C16 176.1(3) . . . . ? Sb1 C10 C11 C16 -0.8(4) . . . . ? C13 C12 C11 C10 -0.5(5) . . . . ? C13 C12 C11 C16 -178.0(3) . . . . ? C17 N2 C16 C11 70.8(3) . . . . ? C18 N2 C16 C11 -166.0(3) . . . . ? C10 C11 C16 N2 66.1(4) . . . . ? C12 C11 C16 N2 -116.5(3) . . . . ? C28 Sb2 C19 C24 -112.5(3) . . . . ? N3 Sb2 C19 C24 162.6(3) . . . . ? Br2 Sb2 C19 C24 -25.1(3) . . . . ? C28 Sb2 C19 C20 72.5(2) . . . . ? N3 Sb2 C19 C20 -12.4(2) . . . . ? Br2 Sb2 C19 C20 159.9(2) . . . . ? C20 C19 C24 C23 -0.5(4) . . . . ? Sb2 C19 C24 C23 -175.4(2) . . . . ? C19 C24 C23 C22 -0.7(5) . . . . ? C24 C23 C22 C21 0.9(5) . . . . ? C23 C22 C21 C20 0.1(5) . . . . ? C22 C21 C20 C19 -1.2(5) . . . . ? C22 C21 C20 C25 -179.4(3) . . . . ? C24 C19 C20 C21 1.4(4) . . . . ? Sb2 C19 C20 C21 176.7(2) . . . . ? C24 C19 C20 C25 179.6(3) . . . . ? Sb2 C19 C20 C25 -5.1(4) . . . . ? C26 N3 C25 C20 76.1(3) . . . . ? C27 N3 C25 C20 -163.2(3) . . . . ? Sb2 N3 C25 C20 -37.1(3) . . . . ? C21 C20 C25 N3 -150.7(3) . . . . ? C19 C20 C25 N3 31.0(4) . . . . ? C19 Sb2 C28 C33 1.6(3) . . . . ? N3 Sb2 C28 C33 75.5(3) . . . . ? Br2 Sb2 C28 C33 -89.4(3) . . . . ? C19 Sb2 C28 C29 179.0(2) . . . . ? N3 Sb2 C28 C29 -107.1(2) . . . . ? Br2 Sb2 C28 C29 88.0(2) . . . . ? C29 C28 C33 C32 3.2(5) . . . . ? Sb2 C28 C33 C32 -179.4(2) . . . . ? C28 C33 C32 C31 -0.9(5) . . . . ? C33 C32 C31 C30 -1.8(5) . . . . ? C32 C31 C30 C29 2.3(5) . . . . ? C31 C30 C29 C28 0.0(5) . . . . ? C31 C30 C29 C34 -177.8(3) . . . . ? C33 C28 C29 C30 -2.7(4) . . . . ? Sb2 C28 C29 C30 179.8(2) . . . . ? C33 C28 C29 C34 175.1(3) . . . . ? Sb2 C28 C29 C34 -2.4(4) . . . . ? C35 N4 C34 C29 -163.5(3) . . . . ? C36 N4 C34 C29 73.7(3) . . . . ? C30 C29 C34 N4 -112.9(3) . . . . ? C28 C29 C34 N4 69.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.917 _refine_diff_density_max 0.457 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.067 data_cs12 _database_code_CSD 211553 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H12 Cl2 N Sb' _chemical_formula_sum 'C9 H12 Cl2 N Sb' _chemical_formula_weight 326.85 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 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' 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' _cell_length_a 11.8382(13) _cell_length_b 14.6215(15) _cell_length_c 6.7329(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1165.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 84 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 12.39 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.863 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 2.782 _exptl_absorpt_correction_type refdelF _exptl_absorpt_correction_T_min 0.4024 _exptl_absorpt_correction_T_max 0.4890 _exptl_absorpt_process_details 'Stuart & Walker, Acta Cryst A (1983)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 197 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'random variation +/-2.0' _diffrn_reflns_number 2930 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2493 _reflns_number_gt 2295 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0646P)^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 refU _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 0.00(4) _refine_ls_number_reflns 2493 _refine_ls_number_parameters 123 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0396 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 Sb1 Sb 0.67526(2) 0.520448(18) 0.20521(7) 0.01890(11) Uani 1 1 d . . . Cl1 Cl 0.84270(13) 0.50521(12) 0.0053(3) 0.0295(3) Uani 1 1 d . . . Cl2 Cl 0.56819(13) 0.43934(10) -0.0745(3) 0.0357(4) Uani 1 1 d . . . N1 N 0.7851(4) 0.6279(3) 0.3950(8) 0.0251(10) Uani 1 1 d . . . C1 C 0.8030(5) 0.7071(4) 0.2621(11) 0.0319(16) Uani 1 1 d . . . H1A H 0.8194 0.7621 0.3427 0.057(19) Uiso 1 1 calc R . . H1B H 0.8691 0.6953 0.1756 0.057(19) Uiso 1 1 calc R . . C2 C 0.7111(6) 0.6518(5) 0.5663(12) 0.0375(16) Uani 1 1 d . . . H2A H 0.7474 0.6995 0.6461 0.052(10) Uiso 1 1 calc R . . H2B H 0.6989 0.5973 0.6485 0.052(10) Uiso 1 1 calc R . . H2C H 0.6383 0.6742 0.5170 0.052(10) Uiso 1 1 calc R . . C3 C 0.8937(5) 0.5912(5) 0.4686(11) 0.0361(15) Uani 1 1 d . . . H3A H 0.9274 0.5518 0.3669 0.052(10) Uiso 1 1 calc R . . H3B H 0.8805 0.5555 0.5896 0.052(10) Uiso 1 1 calc R . . H3C H 0.9451 0.6419 0.4980 0.052(10) Uiso 1 1 calc R . . C4 C 0.7026(5) 0.7239(3) 0.1382(9) 0.0210(11) Uani 1 1 d . . . C5 C 0.6313(4) 0.6520(3) 0.0863(9) 0.0184(10) Uani 1 1 d . . . C6 C 0.5365(5) 0.6659(4) -0.0314(10) 0.0265(12) Uani 1 1 d . . . H6 H 0.4871 0.6165 -0.0604 0.040(10) Uiso 1 1 calc R . . C7 C 0.5147(6) 0.7527(4) -0.1064(11) 0.0322(13) Uani 1 1 d . . . H7 H 0.4512 0.7624 -0.1899 0.040(10) Uiso 1 1 calc R . . C8 C 0.5859(6) 0.8256(4) -0.0592(12) 0.0387(17) Uani 1 1 d . . . H8 H 0.5715 0.8845 -0.1129 0.040(10) Uiso 1 1 calc R . . C9 C 0.6775(6) 0.8122(4) 0.0657(13) 0.0383(18) Uani 1 1 d . . . H9 H 0.7235 0.8626 0.1027 0.040(10) 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 Sb1 0.01886(16) 0.01843(16) 0.01943(18) 0.00159(18) -0.0002(2) 0.00084(10) Cl1 0.0228(6) 0.0390(6) 0.0268(8) -0.0057(7) 0.0043(6) 0.0058(5) Cl2 0.0327(7) 0.0276(6) 0.0467(10) -0.0143(7) -0.0122(7) 0.0022(5) N1 0.024(2) 0.032(2) 0.020(2) -0.005(2) -0.005(2) -0.0015(19) C1 0.029(3) 0.026(3) 0.040(5) -0.004(2) -0.006(3) -0.006(2) C2 0.037(3) 0.044(3) 0.031(4) -0.014(3) 0.004(3) 0.002(3) C3 0.031(3) 0.044(3) 0.033(4) -0.011(3) -0.009(3) 0.008(3) C4 0.030(3) 0.015(2) 0.018(3) 0.0032(18) 0.002(2) -0.001(2) C5 0.019(2) 0.019(2) 0.017(3) 0.0025(19) 0.000(2) 0.0035(18) C6 0.025(3) 0.027(2) 0.028(3) -0.001(2) -0.003(3) 0.006(2) C7 0.034(3) 0.032(3) 0.030(3) 0.008(3) 0.002(3) 0.011(2) C8 0.053(4) 0.023(2) 0.040(4) 0.012(3) 0.006(4) 0.009(3) C9 0.047(4) 0.015(2) 0.053(5) 0.008(3) 0.010(3) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sb1 C5 2.147(5) . ? Sb1 N1 2.406(5) . ? Sb1 Cl1 2.4062(17) . ? Sb1 Cl2 2.5615(16) . ? N1 C3 1.479(8) . ? N1 C1 1.479(8) . ? N1 C2 1.490(9) . ? C1 C4 1.474(8) . ? C4 C5 1.392(8) . ? C4 C9 1.412(8) . ? C5 C6 1.388(8) . ? C6 C7 1.390(8) . ? C7 C8 1.395(10) . ? C8 C9 1.387(11) . ? 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 C5 Sb1 N1 75.2(2) . . ? C5 Sb1 Cl1 94.26(15) . . ? N1 Sb1 Cl1 84.98(13) . . ? C5 Sb1 Cl2 91.18(16) . . ? N1 Sb1 Cl2 163.76(14) . . ? Cl1 Sb1 Cl2 87.33(6) . . ? C3 N1 C1 111.2(5) . . ? C3 N1 C2 109.7(5) . . ? C1 N1 C2 111.7(5) . . ? C3 N1 Sb1 114.3(4) . . ? C1 N1 Sb1 105.5(4) . . ? C2 N1 Sb1 104.3(4) . . ? C4 C1 N1 110.9(5) . . ? C5 C4 C9 118.4(6) . . ? C5 C4 C1 120.4(5) . . ? C9 C4 C1 121.2(5) . . ? C6 C5 C4 121.5(5) . . ? C6 C5 Sb1 122.7(4) . . ? C4 C5 Sb1 115.8(4) . . ? C5 C6 C7 119.4(6) . . ? C6 C7 C8 120.2(6) . . ? C9 C8 C7 120.2(6) . . ? C8 C9 C4 120.2(6) . . ? 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 Sb1 N1 C3 -150.3(5) . . . . ? Cl1 Sb1 N1 C3 -54.6(5) . . . . ? Cl2 Sb1 N1 C3 -116.6(5) . . . . ? C5 Sb1 N1 C1 -27.8(4) . . . . ? Cl1 Sb1 N1 C1 67.9(4) . . . . ? Cl2 Sb1 N1 C1 5.9(7) . . . . ? C5 Sb1 N1 C2 89.9(4) . . . . ? Cl1 Sb1 N1 C2 -174.3(4) . . . . ? Cl2 Sb1 N1 C2 123.7(5) . . . . ? C3 N1 C1 C4 160.9(5) . . . . ? C2 N1 C1 C4 -76.2(6) . . . . ? Sb1 N1 C1 C4 36.5(5) . . . . ? N1 C1 C4 C5 -28.7(8) . . . . ? N1 C1 C4 C9 152.7(6) . . . . ? C9 C4 C5 C6 -0.9(9) . . . . ? C1 C4 C5 C6 -179.5(6) . . . . ? C9 C4 C5 Sb1 -179.5(5) . . . . ? C1 C4 C5 Sb1 1.8(7) . . . . ? N1 Sb1 C5 C6 -164.0(5) . . . . ? Cl1 Sb1 C5 C6 112.4(5) . . . . ? Cl2 Sb1 C5 C6 25.0(5) . . . . ? N1 Sb1 C5 C4 14.6(4) . . . . ? Cl1 Sb1 C5 C4 -69.0(4) . . . . ? Cl2 Sb1 C5 C4 -156.4(4) . . . . ? C4 C5 C6 C7 2.7(10) . . . . ? Sb1 C5 C6 C7 -178.7(5) . . . . ? C5 C6 C7 C8 -1.7(10) . . . . ? C6 C7 C8 C9 -1.2(11) . . . . ? C7 C8 C9 C4 3.1(11) . . . . ? C5 C4 C9 C8 -2.1(10) . . . . ? C1 C4 C9 C8 176.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.678 _refine_diff_density_min -0.697 _refine_diff_density_rms 0.143 data_cs13 _database_code_CSD 211554 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H25 I2 N2 Sb' _chemical_formula_sum 'C18 H25 I2 N2 Sb' _chemical_formula_weight 644.95 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' Sb Sb -0.5866 1.5461 '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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 15.432(3) _cell_length_b 12.241(3) _cell_length_c 12.299(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.96(2) _cell_angle_gamma 90.00 _cell_volume 2244.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 2.514 _cell_measurement_theta_max 12.550 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.909 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 3.981 _exptl_absorpt_correction_type refdelF _exptl_absorpt_correction_T_min 0.1986 _exptl_absorpt_correction_T_max 0.3813 _exptl_absorpt_process_details 'Walker & Stuart, Acta Cryst A (1983)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 197 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'random variation +/-2.0' _diffrn_reflns_number 6467 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5134 _reflns_number_gt 4452 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics DIAMOND _computing_publication_material 'Siemens SHELXTL' _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^)+(0.0420P)^2^+14.6244P] 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 refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5134 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.1026 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Sb1 Sb 0.23499(2) 0.62137(3) 0.34002(3) 0.02236(10) Uani 1 1 d . . . I1 I 0.24341(3) 0.41179(4) 0.45986(4) 0.03546(12) Uani 1 1 d . . . I2 I 0.52568(3) 0.30087(3) 0.06102(3) 0.03464(12) Uani 1 1 d . . . N1 N 0.1988(3) 0.7861(4) 0.2268(4) 0.0294(10) Uani 1 1 d . . . N2 N 0.4657(3) 0.4958(5) 0.2311(5) 0.0348(12) Uani 1 1 d . . . H21 H 0.473(4) 0.443(5) 0.176(5) 0.025(16) Uiso 1 1 d . . . C1 C 0.0921(4) 0.6430(5) 0.3166(5) 0.0271(11) Uani 1 1 d . . . C10 C 0.2257(4) 0.5327(4) 0.1849(4) 0.0244(11) Uani 1 1 d . . . C6 C 0.0422(4) 0.5942(6) 0.3823(5) 0.0341(13) Uani 1 1 d . . . H6 H 0.0691 0.5402 0.4359 0.042(7) Uiso 1 1 calc R . . C5 C -0.0468(4) 0.6235(6) 0.3707(6) 0.0402(15) Uani 1 1 d . . . H5 H -0.0804 0.5892 0.4159 0.042(7) Uiso 1 1 calc R . . C4 C -0.0864(4) 0.7025(6) 0.2932(6) 0.0438(17) Uani 1 1 d . . . H4 H -0.1470 0.7230 0.2859 0.042(7) Uiso 1 1 calc R . . C3 C -0.0376(4) 0.7520(6) 0.2261(6) 0.0405(15) Uani 1 1 d . . . H3 H -0.0650 0.8060 0.1727 0.042(7) Uiso 1 1 calc R . . C2 C 0.0519(4) 0.7220(5) 0.2372(5) 0.0317(13) Uani 1 1 d . . . C7 C 0.1043(4) 0.7735(6) 0.1638(5) 0.0345(13) Uani 1 1 d . . . H7A H 0.1006 0.7272 0.0967 0.040(10) Uiso 1 1 calc R . . H7B H 0.0786 0.8459 0.1378 0.040(10) Uiso 1 1 calc R . . C8 C 0.2080(5) 0.8761(5) 0.3071(6) 0.0405(15) Uani 1 1 d . . . H8A H 0.1848 0.9434 0.2669 0.050(7) Uiso 1 1 calc R . . H8B H 0.2714 0.8859 0.3461 0.050(7) Uiso 1 1 calc R . . H8C H 0.1740 0.8594 0.3622 0.050(7) Uiso 1 1 calc R . . C9 C 0.2571(5) 0.8066(6) 0.1505(6) 0.0382(15) Uani 1 1 d . . . H9A H 0.2400 0.8758 0.1108 0.050(7) Uiso 1 1 calc R . . H9B H 0.2501 0.7470 0.0957 0.050(7) Uiso 1 1 calc R . . H9C H 0.3198 0.8105 0.1944 0.050(7) Uiso 1 1 calc R . . C15 C 0.1445(4) 0.4841(5) 0.1300(5) 0.0317(12) Uani 1 1 d . . . H15 H 0.0932 0.4946 0.1581 0.042(7) Uiso 1 1 calc R . . C14 C 0.1377(5) 0.4202(6) 0.0338(6) 0.0392(15) Uani 1 1 d . . . H14 H 0.0825 0.3856 -0.0016 0.042(7) Uiso 1 1 calc R . . C13 C 0.2109(5) 0.4073(5) -0.0094(5) 0.0364(14) Uani 1 1 d . . . H13 H 0.2060 0.3648 -0.0754 0.042(7) Uiso 1 1 calc R . . C12 C 0.2911(4) 0.4559(5) 0.0430(5) 0.0336(13) Uani 1 1 d . . . H12 H 0.3415 0.4461 0.0130 0.042(7) Uiso 1 1 calc R . . C11 C 0.2999(4) 0.5199(5) 0.1403(4) 0.0251(11) Uani 1 1 d . . . C16 C 0.3895(4) 0.5749(5) 0.1897(5) 0.0302(12) Uani 1 1 d . . . H16A H 0.4038 0.6226 0.1316 0.040(10) Uiso 1 1 calc R . . H16B H 0.3842 0.6220 0.2531 0.040(10) Uiso 1 1 calc R . . C17 C 0.5525(5) 0.5551(7) 0.2601(7) 0.0477(18) Uani 1 1 d . . . H17A H 0.5541 0.6054 0.3226 0.050(7) Uiso 1 1 calc R . . H17B H 0.5590 0.5966 0.1945 0.050(7) Uiso 1 1 calc R . . H17C H 0.6018 0.5025 0.2823 0.050(7) Uiso 1 1 calc R . . C18 C 0.4532(6) 0.4291(8) 0.3264(7) 0.058(2) Uani 1 1 d . . . H18A H 0.5014 0.3749 0.3470 0.050(7) Uiso 1 1 calc R . . H18B H 0.3952 0.3916 0.3041 0.050(7) Uiso 1 1 calc R . . H18C H 0.4548 0.4766 0.3910 0.050(7) 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 Sb1 0.02261(18) 0.02411(19) 0.02030(17) -0.00074(13) 0.00542(13) -0.00097(13) I1 0.0341(2) 0.0328(2) 0.0386(2) 0.00439(17) 0.00778(17) -0.00272(16) I2 0.0377(2) 0.0339(2) 0.0332(2) -0.00005(16) 0.01066(16) 0.00789(16) N1 0.037(3) 0.026(2) 0.026(2) 0.0047(19) 0.008(2) 0.000(2) N2 0.029(3) 0.043(3) 0.031(3) -0.002(2) 0.005(2) 0.009(2) C1 0.026(3) 0.029(3) 0.026(3) -0.005(2) 0.005(2) 0.001(2) C10 0.032(3) 0.020(3) 0.021(2) 0.002(2) 0.007(2) 0.000(2) C6 0.031(3) 0.042(4) 0.030(3) -0.002(3) 0.011(2) 0.000(3) C5 0.032(3) 0.052(4) 0.040(4) -0.008(3) 0.015(3) 0.000(3) C4 0.026(3) 0.052(4) 0.050(4) -0.015(3) 0.004(3) 0.004(3) C3 0.031(3) 0.040(4) 0.043(4) -0.003(3) -0.004(3) 0.011(3) C2 0.030(3) 0.031(3) 0.031(3) -0.003(2) 0.000(2) 0.003(2) C7 0.038(3) 0.035(3) 0.025(3) 0.004(2) -0.001(2) 0.004(3) C8 0.047(4) 0.029(3) 0.042(4) -0.004(3) 0.007(3) 0.000(3) C9 0.047(4) 0.031(3) 0.038(3) 0.009(3) 0.014(3) -0.003(3) C15 0.032(3) 0.033(3) 0.030(3) -0.003(2) 0.006(2) -0.005(2) C14 0.045(4) 0.035(3) 0.033(3) -0.006(3) 0.001(3) -0.011(3) C13 0.053(4) 0.030(3) 0.025(3) -0.006(2) 0.007(3) 0.000(3) C12 0.039(3) 0.037(3) 0.024(3) -0.007(2) 0.006(2) 0.012(3) C11 0.029(3) 0.025(3) 0.020(2) -0.002(2) 0.005(2) 0.004(2) C16 0.024(3) 0.035(3) 0.033(3) 0.001(2) 0.009(2) 0.006(2) C17 0.032(3) 0.055(5) 0.050(4) -0.014(4) 0.001(3) 0.007(3) C18 0.061(5) 0.069(6) 0.044(4) 0.019(4) 0.013(4) 0.023(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 C1 2.165(6) . ? Sb1 C10 2.167(5) . ? Sb1 N1 2.432(5) . ? Sb1 I1 2.9448(8) . ? N1 C8 1.462(8) . ? N1 C7 1.472(8) . ? N1 C9 1.480(8) . ? N2 C18 1.481(9) . ? N2 C17 1.484(9) . ? N2 C16 1.507(8) . ? C1 C6 1.388(8) . ? C1 C2 1.401(8) . ? C10 C15 1.395(8) . ? C10 C11 1.401(8) . ? C6 C5 1.390(9) . ? C5 C4 1.384(11) . ? C4 C3 1.392(11) . ? C3 C2 1.401(9) . ? C2 C7 1.499(9) . ? C15 C14 1.400(9) . ? C14 C13 1.376(10) . ? C13 C12 1.375(10) . ? C12 C11 1.407(8) . ? C11 C16 1.517(8) . ? 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 C1 Sb1 C10 96.4(2) . . ? C1 Sb1 N1 75.3(2) . . ? C10 Sb1 N1 87.59(19) . . ? C1 Sb1 I1 94.88(16) . . ? C10 Sb1 I1 89.35(14) . . ? N1 Sb1 I1 169.36(12) . . ? C8 N1 C7 110.2(5) . . ? C8 N1 C9 109.4(5) . . ? C7 N1 C9 111.4(5) . . ? C8 N1 Sb1 105.7(4) . . ? C7 N1 Sb1 105.3(4) . . ? C9 N1 Sb1 114.6(4) . . ? C18 N2 C17 111.9(6) . . ? C18 N2 C16 111.8(5) . . ? C17 N2 C16 110.2(5) . . ? C6 C1 C2 119.4(6) . . ? C6 C1 Sb1 124.7(5) . . ? C2 C1 Sb1 115.5(4) . . ? C15 C10 C11 119.0(5) . . ? C15 C10 Sb1 119.2(4) . . ? C11 C10 Sb1 121.8(4) . . ? C1 C6 C5 120.8(6) . . ? C4 C5 C6 119.9(7) . . ? C5 C4 C3 120.2(6) . . ? C4 C3 C2 119.9(6) . . ? C1 C2 C3 119.8(6) . . ? C1 C2 C7 119.9(5) . . ? C3 C2 C7 120.2(6) . . ? N1 C7 C2 110.0(5) . . ? C10 C15 C14 120.6(6) . . ? C13 C14 C15 120.1(6) . . ? C12 C13 C14 119.9(6) . . ? C13 C12 C11 121.1(6) . . ? C10 C11 C12 119.2(5) . . ? C10 C11 C16 123.1(5) . . ? C12 C11 C16 117.7(5) . . ? N2 C16 C11 113.7(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 C1 Sb1 N1 C8 89.0(4) . . . . ? C10 Sb1 N1 C8 -173.8(4) . . . . ? I1 Sb1 N1 C8 112.7(7) . . . . ? C1 Sb1 N1 C7 -27.6(4) . . . . ? C10 Sb1 N1 C7 69.6(4) . . . . ? I1 Sb1 N1 C7 -3.9(9) . . . . ? C1 Sb1 N1 C9 -150.5(5) . . . . ? C10 Sb1 N1 C9 -53.3(4) . . . . ? I1 Sb1 N1 C9 -126.7(6) . . . . ? C10 Sb1 C1 C6 112.6(5) . . . . ? N1 Sb1 C1 C6 -161.6(6) . . . . ? I1 Sb1 C1 C6 22.7(5) . . . . ? C10 Sb1 C1 C2 -75.0(5) . . . . ? N1 Sb1 C1 C2 10.8(4) . . . . ? I1 Sb1 C1 C2 -164.9(4) . . . . ? C1 Sb1 C10 C15 -18.5(5) . . . . ? N1 Sb1 C10 C15 -93.4(5) . . . . ? I1 Sb1 C10 C15 76.4(4) . . . . ? C1 Sb1 C10 C11 163.7(5) . . . . ? N1 Sb1 C10 C11 88.7(5) . . . . ? I1 Sb1 C10 C11 -101.5(4) . . . . ? C2 C1 C6 C5 -0.4(9) . . . . ? Sb1 C1 C6 C5 171.7(5) . . . . ? C1 C6 C5 C4 -0.3(10) . . . . ? C6 C5 C4 C3 0.7(11) . . . . ? C5 C4 C3 C2 -0.2(11) . . . . ? C6 C1 C2 C3 0.9(9) . . . . ? Sb1 C1 C2 C3 -172.0(5) . . . . ? C6 C1 C2 C7 -178.6(6) . . . . ? Sb1 C1 C2 C7 8.6(7) . . . . ? C4 C3 C2 C1 -0.5(10) . . . . ? C4 C3 C2 C7 178.9(6) . . . . ? C8 N1 C7 C2 -74.5(6) . . . . ? C9 N1 C7 C2 163.8(5) . . . . ? Sb1 N1 C7 C2 39.0(6) . . . . ? C1 C2 C7 N1 -35.1(8) . . . . ? C3 C2 C7 N1 145.5(6) . . . . ? C11 C10 C15 C14 2.2(9) . . . . ? Sb1 C10 C15 C14 -175.7(5) . . . . ? C10 C15 C14 C13 -1.9(10) . . . . ? C15 C14 C13 C12 1.0(10) . . . . ? C14 C13 C12 C11 -0.5(10) . . . . ? C15 C10 C11 C12 -1.7(8) . . . . ? Sb1 C10 C11 C12 176.2(4) . . . . ? C15 C10 C11 C16 176.3(5) . . . . ? Sb1 C10 C11 C16 -5.9(8) . . . . ? C13 C12 C11 C10 0.9(9) . . . . ? C13 C12 C11 C16 -177.2(6) . . . . ? C18 N2 C16 C11 -64.3(7) . . . . ? C17 N2 C16 C11 170.6(5) . . . . ? C10 C11 C16 N2 118.5(6) . . . . ? C12 C11 C16 N2 -63.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.352 _refine_diff_density_min -2.584 _refine_diff_density_rms 0.164 data_lau2i _database_code_CSD 211555 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H12 Br2 N Sb' _chemical_formula_sum 'C9 H12 Br2 N Sb' _chemical_formula_weight 415.77 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' Br Br -0.2901 2.4595 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 6.9260(10) _cell_length_b 14.515(3) _cell_length_c 12.278(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.63(3) _cell_angle_gamma 90.00 _cell_volume 1233.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 1.15 _cell_measurement_theta_max 25.1 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 8.678 _exptl_absorpt_correction_type refdelF _exptl_absorpt_correction_T_min 0.1289 _exptl_absorpt_correction_T_max 0.1805 _exptl_absorpt_process_details 'Stuart & Walker, Acta Cryst. A (1983)' _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_type 'STOE IPDS' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'random variation +/-2.0' _diffrn_reflns_number 17081 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.94 _reflns_number_total 2383 _reflns_number_gt 2026 _reflns_threshold_expression >2\s(I) _computing_data_collection 'STOE Expose' _computing_cell_refinement 'STOE Cell' _computing_data_reduction 'STOE Integrate' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics DIAMOND _computing_publication_material SHELXL-97 _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^)+(0.0171P)^2^+0.2679P] 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 2383 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0264 _refine_ls_R_factor_gt 0.0198 _refine_ls_wR_factor_ref 0.0438 _refine_ls_wR_factor_gt 0.0427 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 Sb1 Sb 0.51740(3) 0.533299(13) 0.678175(17) 0.02878(7) Uani 1 1 d . . . Br1 Br 0.73476(4) 0.42239(2) 0.54935(3) 0.03554(9) Uani 1 1 d . . . Br2 Br 0.75708(5) 0.49791(3) 0.84035(3) 0.05293(11) Uani 1 1 d . . . N1 N 0.3882(4) 0.6539(2) 0.7883(2) 0.0387(6) Uani 1 1 d . . . C1 C 0.6731(4) 0.65419(19) 0.6327(2) 0.0262(6) Uani 1 1 d . . . C2 C 0.7848(4) 0.6603(2) 0.5407(3) 0.0312(7) Uani 1 1 d . . . H2 H 0.7979 0.6082 0.4948 0.053(5) Uiso 1 1 calc R . . C3 C 0.8761(4) 0.7423(2) 0.5165(3) 0.0394(8) Uani 1 1 d . . . H3 H 0.9515 0.7461 0.4540 0.053(5) Uiso 1 1 calc R . . C4 C 0.8583(5) 0.8181(2) 0.5825(4) 0.0497(10) Uani 1 1 d . . . H4 H 0.9201 0.8742 0.5649 0.053(5) Uiso 1 1 calc R . . C5 C 0.7509(5) 0.8126(2) 0.6740(4) 0.0512(10) Uani 1 1 d . . . H5 H 0.7402 0.8652 0.7195 0.053(5) Uiso 1 1 calc R . . C6 C 0.6571(4) 0.7305(2) 0.7009(3) 0.0362(7) Uani 1 1 d . . . C7 C 0.5465(5) 0.7220(3) 0.8024(3) 0.0468(9) Uani 1 1 d . . . H7A H 0.6353 0.7028 0.8637 0.055(8) Uiso 1 1 calc R . . H7B H 0.4917 0.7828 0.8208 0.055(8) Uiso 1 1 calc R . . C8 C 0.2238(4) 0.6947(3) 0.7224(3) 0.0444(8) Uani 1 1 d . . . H8A H 0.1714 0.7472 0.7617 0.059(5) Uiso 1 1 calc R . . H8B H 0.1226 0.6482 0.7100 0.059(5) Uiso 1 1 calc R . . H8C H 0.2692 0.7157 0.6521 0.059(5) Uiso 1 1 calc R . . C9 C 0.3213(5) 0.6221(3) 0.8942(3) 0.0582(11) Uani 1 1 d . . . H9A H 0.4275 0.5908 0.9347 0.059(5) Uiso 1 1 calc R . . H9B H 0.2132 0.5792 0.8820 0.059(5) Uiso 1 1 calc R . . H9C H 0.2788 0.6751 0.9363 0.059(5) 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 Sb1 0.02849(10) 0.02794(11) 0.03024(12) 0.00349(9) 0.00503(7) 0.00131(8) Br1 0.03645(16) 0.02701(15) 0.0435(2) -0.00407(13) 0.00514(13) 0.00401(12) Br2 0.0532(2) 0.0682(3) 0.0370(2) 0.01185(18) -0.00202(16) 0.02547(18) N1 0.0325(13) 0.0542(17) 0.0295(15) -0.0049(13) 0.0016(11) 0.0158(12) C1 0.0240(13) 0.0242(14) 0.0298(17) -0.0021(12) -0.0056(11) 0.0019(11) C2 0.0257(13) 0.0304(15) 0.0372(18) 0.0026(13) -0.0035(12) -0.0001(12) C3 0.0265(15) 0.0386(18) 0.052(2) 0.0123(16) -0.0054(14) -0.0029(13) C4 0.0362(17) 0.0295(17) 0.082(3) 0.0075(18) -0.0150(18) -0.0052(14) C5 0.046(2) 0.0282(17) 0.077(3) -0.0174(18) -0.0169(19) 0.0056(14) C6 0.0307(15) 0.0303(16) 0.046(2) -0.0098(15) -0.0112(14) 0.0086(12) C7 0.0410(17) 0.056(2) 0.043(2) -0.0221(18) -0.0082(15) 0.0166(16) C8 0.0348(17) 0.060(2) 0.038(2) -0.0035(18) -0.0030(14) 0.0164(16) C9 0.052(2) 0.091(3) 0.032(2) 0.004(2) 0.0117(16) 0.024(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 C1 2.147(3) . ? Sb1 N1 2.409(3) . ? Sb1 Br2 2.5847(8) . ? Sb1 Br1 2.7528(6) . ? N1 C9 1.474(4) . ? N1 C7 1.481(5) . ? N1 C8 1.490(4) . ? C1 C6 1.396(4) . ? C1 C2 1.401(4) . ? C2 C3 1.386(4) . ? C3 C4 1.375(5) . ? C4 C5 1.378(6) . ? C5 C6 1.404(5) . ? C6 C7 1.498(5) . ? 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 C1 Sb1 N1 75.87(11) . . ? C1 Sb1 Br2 92.88(7) . . ? N1 Sb1 Br2 87.36(6) . . ? C1 Sb1 Br1 91.97(8) . . ? N1 Sb1 Br1 167.00(7) . . ? Br2 Sb1 Br1 88.717(16) . . ? C9 N1 C7 111.5(3) . . ? C9 N1 C8 109.9(2) . . ? C7 N1 C8 109.9(3) . . ? C9 N1 Sb1 114.0(2) . . ? C7 N1 Sb1 105.01(18) . . ? C8 N1 Sb1 106.2(2) . . ? C6 C1 C2 119.7(3) . . ? C6 C1 Sb1 116.0(2) . . ? C2 C1 Sb1 124.3(2) . . ? C3 C2 C1 120.1(3) . . ? C4 C3 C2 120.5(3) . . ? C3 C4 C5 120.1(3) . . ? C4 C5 C6 120.9(3) . . ? C1 C6 C5 118.8(3) . . ? C1 C6 C7 119.4(3) . . ? C5 C6 C7 121.7(3) . . ? N1 C7 C6 111.2(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 C1 Sb1 N1 C9 -149.9(2) . . . . ? Br2 Sb1 N1 C9 -56.3(2) . . . . ? Br1 Sb1 N1 C9 -128.9(3) . . . . ? C1 Sb1 N1 C7 -27.6(2) . . . . ? Br2 Sb1 N1 C7 66.1(2) . . . . ? Br1 Sb1 N1 C7 -6.5(4) . . . . ? C1 Sb1 N1 C8 88.9(2) . . . . ? Br2 Sb1 N1 C8 -177.5(2) . . . . ? Br1 Sb1 N1 C8 110.0(3) . . . . ? N1 Sb1 C1 C6 13.4(2) . . . . ? Br2 Sb1 C1 C6 -73.1(2) . . . . ? Br1 Sb1 C1 C6 -162.0(2) . . . . ? N1 Sb1 C1 C2 -166.1(2) . . . . ? Br2 Sb1 C1 C2 107.4(2) . . . . ? Br1 Sb1 C1 C2 18.6(2) . . . . ? C6 C1 C2 C3 -1.1(4) . . . . ? Sb1 C1 C2 C3 178.3(2) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C2 C3 C4 C5 0.7(5) . . . . ? C3 C4 C5 C6 -0.5(5) . . . . ? C2 C1 C6 C5 1.3(4) . . . . ? Sb1 C1 C6 C5 -178.2(2) . . . . ? C2 C1 C6 C7 -176.7(3) . . . . ? Sb1 C1 C6 C7 3.9(3) . . . . ? C4 C5 C6 C1 -0.5(5) . . . . ? C4 C5 C6 C7 177.4(3) . . . . ? C9 N1 C7 C6 161.1(3) . . . . ? C8 N1 C7 C6 -76.7(3) . . . . ? Sb1 N1 C7 C6 37.1(3) . . . . ? C1 C6 C7 N1 -30.5(4) . . . . ? C5 C6 C7 N1 151.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.94 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.355 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.079