# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Darrin Richeson' _publ_contact_author_address ; Department of Chemistry University of Ottawa Ottawa Ontario K1N6N5 CANADA ; _publ_contact_author_email DARRIN@SCIENCE.UOTTAWA.CA _publ_section_title ; Low Coordinate Compounds of Arsenic and Antimony Supported by an Extended pi-Conjugated Framework ; loop_ _publ_author_name 'Darrin Richeson' 'Ilia V. Korobkov' 'Heather A. Spinney' # Attachment 'dr74anew.cif' data_dr74a _database_code_depnum_ccdc_archive 'CCDC 629186' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H26 N3 Sb' _chemical_formula_weight 406.17 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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 14.606(3) _cell_length_b 9.7332(17) _cell_length_c 12.753(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1813.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 969 _cell_measurement_theta_min 2.12 _cell_measurement_theta_max 24.77 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas n/a _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 1.523 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7505 _exptl_absorpt_correction_T_max 0.8626 _exptl_absorpt_process_details 'SADABS, Bruker (2000)' _exptl_special_details ; Data collection is performed with three batch runs at phi = 0.00 deg (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg (650 frames). A fourth batch run is collected at phi = 0.00 deg (50 frames) to monitor crystal and diffractometer stability. Frame width = 0.30 deg in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data. ; _diffrn_ambient_temperature 203(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_% <1 _diffrn_reflns_number 12716 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 24.80 _reflns_number_total 3066 _reflns_number_gt 2578 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker (2000)' _computing_cell_refinement 'SMART, Bruker (2000)' _computing_data_reduction 'XPREP, Bruker (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker (2000)' _computing_publication_material 'SHELXTL, Bruker (2000)' _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^)+(0.0279P)^2^+1.9366P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(4) _refine_ls_number_reflns 3066 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0643 _refine_ls_wR_factor_gt 0.0599 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.001 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 0.533599(13) 0.00114(3) 0.62075(9) 0.03332(9) Uani 1 1 d . . . N1 N 0.5708(2) 0.1370(3) 0.5086(3) 0.0353(7) Uani 1 1 d . . . N2 N 0.4644(2) -0.0982(4) 0.5056(3) 0.0425(8) Uani 1 1 d . . . N3 N 0.4225(2) 0.1126(4) 0.6716(3) 0.0422(8) Uani 1 1 d . . . C1 C 0.5055(3) 0.1940(4) 0.4433(3) 0.0351(9) Uani 1 1 d . . . C2 C 0.5172(4) 0.3255(5) 0.4017(4) 0.0545(13) Uani 1 1 d . . . H2A H 0.5706 0.3745 0.4187 0.065 Uiso 1 1 calc R . . C3 C 0.4532(5) 0.3871(6) 0.3364(4) 0.0658(16) Uani 1 1 d . . . H3A H 0.4645 0.4755 0.3096 0.079 Uiso 1 1 calc R . . C4 C 0.3762(4) 0.3221(7) 0.3113(4) 0.0677(17) Uani 1 1 d . . . H4A H 0.3323 0.3670 0.2696 0.081 Uiso 1 1 calc R . . C5 C 0.3591(3) 0.1878(6) 0.3458(3) 0.0548(14) Uani 1 1 d . . . C6 C 0.4235(3) 0.1181(4) 0.4132(3) 0.0372(10) Uani 1 1 d . . . C7 C 0.2801(4) 0.1185(9) 0.3119(4) 0.0715(18) Uani 1 1 d . . . H7A H 0.2376 0.1648 0.2692 0.086 Uiso 1 1 calc R . . C8 C 0.2638(4) -0.0127(9) 0.3392(5) 0.078(2) Uani 1 1 d . . . H8A H 0.2111 -0.0574 0.3143 0.094 Uiso 1 1 calc R . . C9 C 0.3247(3) -0.0833(7) 0.4044(4) 0.0663(16) Uani 1 1 d . . . H9A H 0.3113 -0.1747 0.4228 0.080 Uiso 1 1 calc R . . C10 C 0.4042(3) -0.0236(5) 0.4431(4) 0.0466(13) Uani 1 1 d . . . C11 C 0.6650(3) 0.1949(5) 0.5127(4) 0.0516(12) Uani 1 1 d . . . H11A H 0.6770 0.2379 0.4437 0.062 Uiso 1 1 calc R . . C12 C 0.6774(4) 0.3073(6) 0.5957(5) 0.0767(18) Uani 1 1 d . . . H12A H 0.6321 0.3788 0.5849 0.115 Uiso 1 1 calc R . . H12B H 0.7383 0.3463 0.5898 0.115 Uiso 1 1 calc R . . H12C H 0.6696 0.2679 0.6650 0.115 Uiso 1 1 calc R . . C13 C 0.7346(3) 0.0823(7) 0.5264(4) 0.0647(15) Uani 1 1 d . . . H13A H 0.7261 0.0135 0.4722 0.097 Uiso 1 1 calc R . . H13B H 0.7269 0.0403 0.5947 0.097 Uiso 1 1 calc R . . H13C H 0.7957 0.1207 0.5209 0.097 Uiso 1 1 calc R . . C14 C 0.4630(5) -0.2512(5) 0.5082(5) 0.0664(16) Uani 1 1 d . . . H14A H 0.4379 -0.2832 0.4404 0.080 Uiso 1 1 calc R . . C15 C 0.4008(6) -0.3048(7) 0.5938(5) 0.111(3) Uani 1 1 d . . . H15A H 0.3398 -0.2673 0.5845 0.167 Uiso 1 1 calc R . . H15B H 0.4245 -0.2771 0.6617 0.167 Uiso 1 1 calc R . . H15C H 0.3982 -0.4043 0.5902 0.167 Uiso 1 1 calc R . . C16 C 0.5581(5) -0.3072(6) 0.5178(5) 0.086(2) Uani 1 1 d . . . H16A H 0.5958 -0.2708 0.4616 0.129 Uiso 1 1 calc R . . H16B H 0.5563 -0.4066 0.5131 0.129 Uiso 1 1 calc R . . H16C H 0.5839 -0.2803 0.5848 0.129 Uiso 1 1 calc R . . C17 C 0.4393(5) 0.2537(6) 0.6982(5) 0.0692(17) Uani 1 1 d . . . H17A H 0.3825 0.2963 0.7207 0.104 Uiso 1 1 calc R . . H17B H 0.4629 0.3018 0.6373 0.104 Uiso 1 1 calc R . . H17C H 0.4837 0.2583 0.7546 0.104 Uiso 1 1 calc R . . C18 C 0.3731(4) 0.0423(7) 0.7543(5) 0.0694(17) Uani 1 1 d . . . H18A H 0.3213 0.0979 0.7760 0.104 Uiso 1 1 calc R . . H18B H 0.4135 0.0278 0.8136 0.104 Uiso 1 1 calc R . . H18C H 0.3514 -0.0456 0.7286 0.104 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 0.03312(13) 0.03471(13) 0.03212(12) 0.00425(11) 0.0016(2) 0.00105(12) N1 0.0350(18) 0.0337(18) 0.0372(18) 0.0090(16) -0.0031(16) -0.0033(14) N2 0.046(2) 0.038(2) 0.043(2) -0.0083(18) 0.0031(17) -0.0069(16) N3 0.038(2) 0.051(2) 0.0377(18) -0.0062(17) -0.0008(16) 0.0043(17) C1 0.044(2) 0.035(2) 0.0266(19) -0.0009(17) 0.0010(18) 0.0071(19) C2 0.075(4) 0.045(3) 0.043(3) 0.006(2) -0.006(2) 0.004(2) C3 0.102(5) 0.052(3) 0.043(3) 0.011(3) -0.005(3) 0.021(3) C4 0.079(4) 0.087(4) 0.038(3) 0.005(3) -0.011(3) 0.050(4) C5 0.040(3) 0.093(4) 0.031(2) -0.023(3) -0.0060(18) 0.025(3) C6 0.033(2) 0.052(3) 0.027(2) -0.0080(19) 0.0013(16) 0.0079(19) C7 0.041(3) 0.128(6) 0.046(3) -0.030(4) -0.013(2) 0.027(4) C8 0.036(3) 0.144(7) 0.056(3) -0.053(4) 0.001(2) -0.011(4) C9 0.050(3) 0.093(4) 0.056(3) -0.030(3) 0.007(3) -0.021(3) C10 0.037(3) 0.060(3) 0.043(3) -0.024(2) 0.009(2) -0.002(2) C11 0.041(2) 0.067(3) 0.047(2) 0.020(2) -0.004(2) -0.021(2) C12 0.067(3) 0.077(4) 0.086(5) 0.007(3) -0.022(3) -0.035(3) C13 0.035(3) 0.106(5) 0.053(3) 0.022(3) -0.001(2) -0.002(3) C14 0.111(5) 0.040(3) 0.049(3) -0.008(2) 0.010(3) -0.023(3) C15 0.180(8) 0.079(4) 0.075(5) -0.001(3) 0.021(5) -0.070(5) C16 0.139(6) 0.050(3) 0.068(4) -0.002(3) -0.006(4) 0.034(4) C17 0.072(4) 0.071(4) 0.064(4) -0.014(3) -0.004(3) 0.018(3) C18 0.055(3) 0.095(4) 0.058(4) 0.004(3) 0.021(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 N1 2.022(3) . ? Sb1 N2 2.028(4) . ? Sb1 N3 2.056(4) . ? N1 C1 1.382(5) . ? N1 C11 1.488(5) . ? N2 C10 1.391(6) . ? N2 C14 1.489(6) . ? N3 C17 1.436(7) . ? N3 C18 1.450(7) . ? C1 C2 1.396(6) . ? C1 C6 1.459(6) . ? C2 C3 1.388(7) . ? C3 C4 1.331(9) . ? C4 C5 1.401(9) . ? C5 C7 1.406(8) . ? C5 C6 1.443(6) . ? C6 C10 1.458(6) . ? C7 C8 1.345(9) . ? C8 C9 1.398(9) . ? C9 C10 1.389(7) . ? C11 C13 1.505(7) . ? C11 C12 1.533(8) . ? C14 C16 1.497(8) . ? C14 C15 1.513(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 N1 Sb1 N2 86.19(16) . . ? N1 Sb1 N3 95.16(14) . . ? N2 Sb1 N3 94.96(15) . . ? C1 N1 C11 120.5(3) . . ? C1 N1 Sb1 120.2(3) . . ? C11 N1 Sb1 118.1(3) . . ? C10 N2 C14 121.7(4) . . ? C10 N2 Sb1 118.8(3) . . ? C14 N2 Sb1 117.9(4) . . ? C17 N3 C18 111.3(4) . . ? C17 N3 Sb1 116.4(3) . . ? C18 N3 Sb1 111.9(3) . . ? C2 C1 N1 120.8(4) . . ? C2 C1 C6 117.7(4) . . ? N1 C1 C6 121.5(4) . . ? C1 C2 C3 122.8(5) . . ? C4 C3 C2 120.5(5) . . ? C3 C4 C5 121.2(5) . . ? C7 C5 C4 119.8(5) . . ? C7 C5 C6 119.5(6) . . ? C4 C5 C6 120.7(5) . . ? C5 C6 C10 118.4(4) . . ? C5 C6 C1 117.0(4) . . ? C10 C6 C1 124.6(4) . . ? C8 C7 C5 121.4(6) . . ? C7 C8 C9 120.6(5) . . ? C8 C9 C10 122.5(6) . . ? N2 C10 C9 120.9(5) . . ? N2 C10 C6 121.5(4) . . ? C9 C10 C6 117.6(5) . . ? C13 C11 N1 110.7(4) . . ? C13 C11 C12 111.1(4) . . ? N1 C11 C12 113.8(4) . . ? C16 C14 N2 110.7(5) . . ? C16 C14 C15 111.9(6) . . ? N2 C14 C15 111.7(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 N2 Sb1 N1 C1 49.9(3) . . . . ? N3 Sb1 N1 C1 -44.8(3) . . . . ? N2 Sb1 N1 C11 -142.5(3) . . . . ? N3 Sb1 N1 C11 122.8(3) . . . . ? N1 Sb1 N2 C10 -51.4(3) . . . . ? N3 Sb1 N2 C10 43.4(4) . . . . ? N1 Sb1 N2 C14 143.0(4) . . . . ? N3 Sb1 N2 C14 -122.2(4) . . . . ? N1 Sb1 N3 C17 -52.4(4) . . . . ? N2 Sb1 N3 C17 -139.0(4) . . . . ? N1 Sb1 N3 C18 177.9(4) . . . . ? N2 Sb1 N3 C18 91.3(4) . . . . ? C11 N1 C1 C2 -17.2(6) . . . . ? Sb1 N1 C1 C2 150.1(3) . . . . ? C11 N1 C1 C6 161.2(4) . . . . ? Sb1 N1 C1 C6 -31.5(5) . . . . ? N1 C1 C2 C3 -179.6(5) . . . . ? C6 C1 C2 C3 1.9(7) . . . . ? C1 C2 C3 C4 0.8(8) . . . . ? C2 C3 C4 C5 -3.0(8) . . . . ? C3 C4 C5 C7 -175.5(5) . . . . ? C3 C4 C5 C6 2.4(7) . . . . ? C7 C5 C6 C10 0.5(6) . . . . ? C4 C5 C6 C10 -177.4(4) . . . . ? C7 C5 C6 C1 178.2(4) . . . . ? C4 C5 C6 C1 0.4(6) . . . . ? C2 C1 C6 C5 -2.4(6) . . . . ? N1 C1 C6 C5 179.2(4) . . . . ? C2 C1 C6 C10 175.2(4) . . . . ? N1 C1 C6 C10 -3.3(6) . . . . ? C4 C5 C7 C8 176.6(5) . . . . ? C6 C5 C7 C8 -1.3(7) . . . . ? C5 C7 C8 C9 1.4(8) . . . . ? C7 C8 C9 C10 -0.6(8) . . . . ? C14 N2 C10 C9 18.7(7) . . . . ? Sb1 N2 C10 C9 -146.3(4) . . . . ? C14 N2 C10 C6 -159.5(4) . . . . ? Sb1 N2 C10 C6 35.5(6) . . . . ? C8 C9 C10 N2 -178.3(5) . . . . ? C8 C9 C10 C6 -0.1(7) . . . . ? C5 C6 C10 N2 178.4(4) . . . . ? C1 C6 C10 N2 0.8(7) . . . . ? C5 C6 C10 C9 0.2(6) . . . . ? C1 C6 C10 C9 -177.4(4) . . . . ? C1 N1 C11 C13 -143.6(4) . . . . ? Sb1 N1 C11 C13 48.9(5) . . . . ? C1 N1 C11 C12 90.5(5) . . . . ? Sb1 N1 C11 C12 -77.1(5) . . . . ? C10 N2 C14 C16 143.2(5) . . . . ? Sb1 N2 C14 C16 -51.7(6) . . . . ? C10 N2 C14 C15 -91.5(7) . . . . ? Sb1 N2 C14 C15 73.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 24.80 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.437 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.061 data_dr25 _database_code_depnum_ccdc_archive 'CCDC 629187' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37.60 H46.40 Cl2 N4 Sb2' _chemical_formula_weight 868.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 15.669(4) _cell_length_b 11.931(3) _cell_length_c 21.118(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.125(4) _cell_angle_gamma 90.00 _cell_volume 3945.3(15) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 711 _cell_measurement_theta_min 1.59 _cell_measurement_theta_max 26.37 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas n/a _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 1.535 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6560 _exptl_absorpt_correction_T_max 0.7489 _exptl_absorpt_process_details 'SADABS, Bruker (2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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_% <1 _diffrn_reflns_number 18116 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 26.37 _reflns_number_total 7934 _reflns_number_gt 5939 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0663P)^2^+7.7637P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7934 _refine_ls_number_parameters 381 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 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 0.88205(2) 0.90468(3) 0.16102(2) 0.04401(13) Uani 1 1 d . . . Cl1 Cl 0.84812(13) 0.82511(16) 0.05918(9) 0.0679(5) Uani 1 1 d . . . N1 N 0.7636(3) 0.8938(4) 0.1953(3) 0.0463(12) Uani 1 1 d . . . N2 N 0.8522(3) 1.0644(4) 0.1381(2) 0.0372(10) Uani 1 1 d . . . C1 C 0.6932(4) 0.9294(5) 0.1579(3) 0.0409(13) Uani 1 1 d . . . C2 C 0.6140(4) 0.8792(6) 0.1635(4) 0.0594(18) Uani 1 1 d . . . H2A H 0.6093 0.8193 0.1921 0.071 Uiso 1 1 calc R . . C3 C 0.5411(4) 0.9134(6) 0.1289(4) 0.066(2) Uani 1 1 d . . . H3A H 0.4888 0.8769 0.1346 0.080 Uiso 1 1 calc R . . C4 C 0.5454(4) 0.9980(6) 0.0879(3) 0.0535(17) Uani 1 1 d . . . H4A H 0.4960 1.0202 0.0645 0.064 Uiso 1 1 calc R . . C5 C 0.6228(3) 1.0543(5) 0.0790(3) 0.0404(13) Uani 1 1 d . . . C6 C 0.6244(4) 1.1450(6) 0.0368(3) 0.0495(16) Uani 1 1 d . . . H6A H 0.5738 1.1651 0.0142 0.059 Uiso 1 1 calc R . . C7 C 0.6960(4) 1.2041(5) 0.0276(3) 0.0471(15) Uani 1 1 d . . . H7A H 0.6951 1.2654 -0.0003 0.057 Uiso 1 1 calc R . . C8 C 0.7728(4) 1.1731(5) 0.0605(3) 0.0418(13) Uani 1 1 d . . . H8A H 0.8230 1.2132 0.0528 0.050 Uiso 1 1 calc R . . C9 C 0.7762(3) 1.0862(4) 0.1035(2) 0.0331(11) Uani 1 1 d . . . C10 C 0.6999(3) 1.0215(4) 0.1141(2) 0.0341(11) Uani 1 1 d . . . C11 C 0.7532(5) 0.8102(6) 0.2464(3) 0.0618(19) Uani 1 1 d . . . H11A H 0.6952 0.8198 0.2627 0.074 Uiso 1 1 calc R . . C12 C 0.8161(6) 0.8326(8) 0.3007(4) 0.085(3) Uani 1 1 d . . . H12A H 0.8092 0.9089 0.3155 0.127 Uiso 1 1 calc R . . H12B H 0.8738 0.8225 0.2864 0.127 Uiso 1 1 calc R . . H12C H 0.8059 0.7808 0.3350 0.127 Uiso 1 1 calc R . . C13 C 0.7595(6) 0.6889(7) 0.2209(4) 0.088(3) Uani 1 1 d . . . H13A H 0.7170 0.6779 0.1869 0.132 Uiso 1 1 calc R . . H13B H 0.7495 0.6363 0.2548 0.132 Uiso 1 1 calc R . . H13C H 0.8161 0.6766 0.2050 0.132 Uiso 1 1 calc R . . C14 C 0.9259(3) 1.1414(5) 0.1325(3) 0.0449(14) Uani 1 1 d . . . H14A H 0.9028 1.2180 0.1267 0.054 Uiso 1 1 calc R . . C15 C 0.9795(4) 1.1405(7) 0.1944(3) 0.0592(18) Uani 1 1 d . . . H15A H 0.9434 1.1580 0.2294 0.089 Uiso 1 1 calc R . . H15B H 1.0245 1.1961 0.1923 0.089 Uiso 1 1 calc R . . H15C H 1.0046 1.0669 0.2008 0.089 Uiso 1 1 calc R . . C16 C 0.9788(4) 1.1160(7) 0.0759(3) 0.0580(17) Uani 1 1 d . . . H16A H 0.9428 1.1184 0.0376 0.087 Uiso 1 1 calc R . . H16B H 1.0038 1.0419 0.0806 0.087 Uiso 1 1 calc R . . H16C H 1.0239 1.1713 0.0732 0.087 Uiso 1 1 calc R . . Sb2 Sb 0.24864(2) 1.06941(3) 0.245006(17) 0.03410(12) Uani 1 1 d . . . Cl2 Cl 0.34144(10) 0.90995(13) 0.26229(8) 0.0512(4) Uani 1 1 d . . . N3 N 0.1495(3) 1.0074(4) 0.2921(2) 0.0352(10) Uani 1 1 d . . . N4 N 0.1898(3) 1.0154(4) 0.1641(2) 0.0340(10) Uani 1 1 d . . . C17 C 0.1161(3) 0.9007(4) 0.2775(3) 0.0353(12) Uani 1 1 d . . . C18 C 0.0784(4) 0.8380(5) 0.3246(3) 0.0471(15) Uani 1 1 d . . . H18A H 0.0781 0.8669 0.3660 0.057 Uiso 1 1 calc R . . C19 C 0.0411(4) 0.7333(6) 0.3122(3) 0.0535(16) Uani 1 1 d . . . H19A H 0.0164 0.6935 0.3453 0.064 Uiso 1 1 calc R . . C20 C 0.0400(4) 0.6894(5) 0.2545(3) 0.0503(16) Uani 1 1 d . . . H20A H 0.0137 0.6196 0.2470 0.060 Uiso 1 1 calc R . . C21 C 0.0784(3) 0.7473(4) 0.2035(3) 0.0408(13) Uani 1 1 d . . . C22 C 0.0742(4) 0.6979(5) 0.1436(3) 0.0511(16) Uani 1 1 d . . . H22A H 0.0484 0.6274 0.1380 0.061 Uiso 1 1 calc R . . C23 C 0.1073(4) 0.7515(5) 0.0932(3) 0.0560(17) Uani 1 1 d . . . H23A H 0.1028 0.7187 0.0527 0.067 Uiso 1 1 calc R . . C24 C 0.1481(4) 0.8548(5) 0.1012(3) 0.0456(14) Uani 1 1 d . . . H24A H 0.1728 0.8890 0.0662 0.055 Uiso 1 1 calc R . . C25 C 0.1529(3) 0.9080(4) 0.1595(3) 0.0338(11) Uani 1 1 d . . . C26 C 0.1174(3) 0.8547(4) 0.2137(3) 0.0347(12) Uani 1 1 d . . . C27 C 0.1378(4) 1.0558(5) 0.3554(3) 0.0408(13) Uani 1 1 d . . . H27A H 0.0818 1.0297 0.3699 0.049 Uiso 1 1 calc R . . C28 C 0.1348(5) 1.1841(5) 0.3528(3) 0.0553(17) Uani 1 1 d . . . H28A H 0.0909 1.2076 0.3220 0.083 Uiso 1 1 calc R . . H28B H 0.1897 1.2126 0.3405 0.083 Uiso 1 1 calc R . . H28C H 0.1218 1.2133 0.3942 0.083 Uiso 1 1 calc R . . C29 C 0.2060(4) 1.0168(6) 0.4044(3) 0.0531(16) Uani 1 1 d . . . H29A H 0.2069 0.9356 0.4058 0.080 Uiso 1 1 calc R . . H29B H 0.1929 1.0460 0.4458 0.080 Uiso 1 1 calc R . . H29C H 0.2615 1.0443 0.3926 0.080 Uiso 1 1 calc R . . C30 C 0.2185(4) 1.0721(5) 0.1053(3) 0.0394(12) Uani 1 1 d . . . H30A H 0.1776 1.0518 0.0703 0.047 Uiso 1 1 calc R . . C31 C 0.2161(4) 1.1986(5) 0.1127(3) 0.0470(14) Uani 1 1 d . . . H31A H 0.1594 1.2215 0.1243 0.071 Uiso 1 1 calc R . . H31B H 0.2299 1.2337 0.0730 0.071 Uiso 1 1 calc R . . H31C H 0.2574 1.2214 0.1456 0.071 Uiso 1 1 calc R . . C32 C 0.3065(4) 1.0316(6) 0.0870(3) 0.0560(17) Uani 1 1 d . . . H32A H 0.3058 0.9507 0.0826 0.084 Uiso 1 1 calc R . . H32B H 0.3485 1.0529 0.1197 0.084 Uiso 1 1 calc R . . H32C H 0.3211 1.0655 0.0471 0.084 Uiso 1 1 calc R . . C33 C 1.0015(9) 0.4319(14) 0.0716(6) 0.070(3) Uiso 0.30 1 d PGD A -1 H33 H 1.0116 0.3924 0.1097 0.084 Uiso 0.30 1 calc PR A -1 C34 C 1.0655(7) 0.4405(15) 0.0280(8) 0.070(3) Uiso 0.30 1 d PG A -1 H34 H 1.1189 0.4068 0.0366 0.084 Uiso 0.30 1 calc PR A -1 C35 C 1.0506(9) 0.4989(17) -0.0282(7) 0.070(3) Uiso 0.30 1 d PG A -1 H35 H 1.0939 0.5047 -0.0577 0.084 Uiso 0.30 1 calc PR A -1 C36 C 0.9716(10) 0.5488(15) -0.0409(6) 0.070(3) Uiso 0.30 1 d PG A -1 H36 H 0.9615 0.5883 -0.0789 0.084 Uiso 0.30 1 calc PR A -1 C37 C 0.9076(8) 0.5402(14) 0.0027(7) 0.070(3) Uiso 0.30 1 d PGD A -1 H37 H 0.8542 0.5740 -0.0059 0.084 Uiso 0.30 1 calc PR A -1 C38 C 0.9226(8) 0.4818(14) 0.0590(6) 0.070(3) Uiso 0.30 1 d PGD A -1 C39 C 0.8603(13) 0.480(2) 0.1051(10) 0.070(3) Uiso 0.30 1 d PD A -1 H39A H 0.8821 0.4392 0.1421 0.104 Uiso 0.30 1 calc PR A -1 H39B H 0.8093 0.4428 0.0880 0.104 Uiso 0.30 1 calc PR A -1 H39C H 0.8464 0.5559 0.1171 0.104 Uiso 0.30 1 calc PR A -1 C40 C 0.9954(10) -0.0860(11) 0.4833(8) 0.114(3) Uiso 0.50 1 d PGD B -2 H40 H 1.0103 -0.1622 0.4807 0.137 Uiso 0.50 1 calc PR B -2 C41 C 0.9308(9) -0.0429(13) 0.4436(7) 0.114(3) Uiso 0.50 1 d PG B -2 H41 H 0.9020 -0.0898 0.4141 0.137 Uiso 0.50 1 calc PR B -2 C42 C 0.9087(9) 0.0697(14) 0.4474(7) 0.114(3) Uiso 0.50 1 d PG B -2 H42 H 0.8650 0.0989 0.4206 0.137 Uiso 0.50 1 calc PR B -2 C43 C 0.9513(9) 0.1391(11) 0.4910(7) 0.114(3) Uiso 0.50 1 d PG B -2 H43 H 0.9364 0.2152 0.4936 0.137 Uiso 0.50 1 calc PR B -2 C44 C 1.0159(9) 0.0960(12) 0.5307(7) 0.114(3) Uiso 0.50 1 d PGD B -2 H44 H 1.0447 0.1429 0.5602 0.137 Uiso 0.50 1 calc PR B -2 C45 C 1.0380(10) -0.0166(12) 0.5269(8) 0.114(3) Uiso 0.50 1 d PGD B -2 C46 C 1.1129(14) -0.0595(17) 0.5698(11) 0.114(3) Uiso 0.50 1 d PD B -2 H46A H 1.1356 0.0019 0.5954 0.171 Uiso 0.50 1 calc PR B -2 H46B H 1.1574 -0.0889 0.5437 0.171 Uiso 0.50 1 calc PR B -2 H46C H 1.0928 -0.1183 0.5972 0.171 Uiso 0.50 1 calc PR B -2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb1 0.0377(2) 0.0444(2) 0.0496(3) 0.00966(18) -0.00213(17) 0.00880(16) Cl1 0.0855(13) 0.0603(11) 0.0579(11) -0.0143(8) 0.0047(9) 0.0155(9) N1 0.038(2) 0.046(3) 0.055(3) 0.010(2) 0.003(2) -0.003(2) N2 0.036(2) 0.039(3) 0.037(3) 0.005(2) -0.0002(19) 0.0015(19) C1 0.039(3) 0.044(3) 0.040(3) -0.001(3) 0.002(2) 0.003(2) C2 0.049(4) 0.059(4) 0.071(5) 0.009(4) 0.002(3) -0.015(3) C3 0.038(3) 0.068(5) 0.094(6) 0.000(4) 0.001(3) -0.012(3) C4 0.031(3) 0.060(4) 0.068(4) -0.016(4) -0.008(3) 0.002(3) C5 0.034(3) 0.046(3) 0.042(3) -0.016(3) -0.001(2) 0.009(2) C6 0.051(4) 0.053(4) 0.044(4) -0.010(3) -0.012(3) 0.022(3) C7 0.059(4) 0.048(4) 0.034(3) 0.005(3) -0.005(3) 0.016(3) C8 0.046(3) 0.040(3) 0.040(3) 0.006(3) 0.001(2) 0.001(2) C9 0.036(3) 0.034(3) 0.029(3) -0.009(2) 0.005(2) 0.003(2) C10 0.035(3) 0.035(3) 0.032(3) -0.004(2) 0.003(2) 0.004(2) C11 0.070(4) 0.062(5) 0.054(4) 0.024(3) 0.002(3) -0.012(4) C12 0.097(6) 0.098(7) 0.057(5) 0.029(5) -0.013(4) -0.013(5) C13 0.118(7) 0.061(5) 0.086(6) 0.025(5) 0.013(5) 0.000(5) C14 0.031(3) 0.042(3) 0.062(4) 0.005(3) -0.003(3) -0.002(2) C15 0.045(4) 0.076(5) 0.056(4) -0.004(4) -0.007(3) -0.008(3) C16 0.042(3) 0.074(5) 0.058(4) 0.005(4) 0.006(3) -0.008(3) Sb2 0.03495(19) 0.03164(19) 0.0355(2) -0.00541(15) -0.00092(14) -0.00451(14) Cl2 0.0451(8) 0.0474(9) 0.0607(10) 0.0007(7) -0.0030(7) 0.0072(6) N3 0.039(2) 0.033(2) 0.034(2) -0.0041(19) 0.0077(19) -0.0018(19) N4 0.036(2) 0.030(2) 0.036(2) -0.0075(19) -0.0026(18) -0.0035(18) C17 0.030(2) 0.030(3) 0.046(3) 0.002(2) 0.001(2) 0.005(2) C18 0.047(3) 0.045(4) 0.049(4) 0.002(3) 0.009(3) -0.003(3) C19 0.045(3) 0.049(4) 0.067(5) 0.013(3) 0.014(3) -0.006(3) C20 0.039(3) 0.034(3) 0.078(5) 0.005(3) 0.000(3) -0.005(2) C21 0.030(3) 0.028(3) 0.063(4) -0.001(3) -0.006(2) 0.001(2) C22 0.055(4) 0.025(3) 0.072(5) -0.010(3) -0.014(3) 0.000(3) C23 0.078(5) 0.037(3) 0.052(4) -0.014(3) -0.018(3) -0.004(3) C24 0.058(4) 0.037(3) 0.041(3) -0.008(3) -0.003(3) -0.002(3) C25 0.035(3) 0.025(3) 0.041(3) -0.004(2) -0.006(2) 0.003(2) C26 0.028(2) 0.032(3) 0.044(3) -0.002(2) -0.005(2) 0.005(2) C27 0.048(3) 0.039(3) 0.035(3) -0.004(2) 0.008(2) 0.005(2) C28 0.090(5) 0.039(3) 0.037(3) -0.003(3) 0.008(3) 0.018(3) C29 0.068(4) 0.053(4) 0.037(3) 0.000(3) -0.002(3) 0.006(3) C30 0.048(3) 0.040(3) 0.031(3) -0.004(2) 0.006(2) -0.007(2) C31 0.065(4) 0.041(3) 0.035(3) 0.005(3) 0.005(3) -0.005(3) C32 0.047(3) 0.067(4) 0.055(4) -0.017(3) 0.015(3) 0.002(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 N2 2.017(4) . ? Sb1 N1 2.021(5) . ? Sb1 Cl1 2.3926(19) . ? N1 C1 1.398(7) . ? N1 C11 1.484(8) . ? N2 C9 1.398(7) . ? N2 C14 1.484(7) . ? C1 C2 1.387(8) . ? C1 C10 1.443(8) . ? C2 C3 1.395(10) . ? C3 C4 1.334(10) . ? C4 C5 1.405(8) . ? C5 C6 1.403(9) . ? C5 C10 1.447(7) . ? C6 C7 1.345(9) . ? C7 C8 1.415(8) . ? C8 C9 1.378(8) . ? C9 C10 1.448(7) . ? C11 C12 1.506(10) . ? C11 C13 1.548(11) . ? C14 C16 1.509(9) . ? C14 C15 1.528(8) . ? Sb2 N3 2.016(4) . ? Sb2 N4 2.017(4) . ? Sb2 Cl2 2.4141(16) . ? N3 C17 1.406(7) . ? N3 C27 1.474(7) . ? N4 C25 1.409(6) . ? N4 C30 1.497(7) . ? C17 C18 1.394(8) . ? C17 C26 1.455(8) . ? C18 C19 1.400(9) . ? C19 C20 1.326(9) . ? C20 C21 1.431(8) . ? C21 C22 1.396(9) . ? C21 C26 1.431(7) . ? C22 C23 1.360(9) . ? C23 C24 1.395(9) . ? C24 C25 1.386(8) . ? C25 C26 1.439(8) . ? C27 C29 1.532(8) . ? C27 C28 1.532(8) . ? C30 C31 1.519(8) . ? C30 C32 1.523(8) . ? C33 C34 1.3900 . ? C33 C38 1.3900 . ? C34 C35 1.3900 . ? C35 C36 1.3900 . ? C36 C37 1.3900 . ? C37 C38 1.3900 . ? C38 C39 1.405(16) . ? C40 C41 1.3900 . ? C40 C45 1.3900 . ? C41 C42 1.3900 . ? C42 C43 1.3900 . ? C43 C44 1.3900 . ? C44 C45 1.3900 . ? C45 C46 1.543(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Sb1 N1 86.49(19) . . ? N2 Sb1 Cl1 96.73(14) . . ? N1 Sb1 Cl1 96.87(16) . . ? C1 N1 C11 120.7(5) . . ? C1 N1 Sb1 119.6(4) . . ? C11 N1 Sb1 115.5(4) . . ? C9 N2 C14 119.6(4) . . ? C9 N2 Sb1 119.1(3) . . ? C14 N2 Sb1 115.4(3) . . ? C2 C1 N1 120.6(6) . . ? C2 C1 C10 118.0(5) . . ? N1 C1 C10 121.3(5) . . ? C3 C2 C1 123.2(7) . . ? C4 C3 C2 120.1(6) . . ? C3 C4 C5 120.9(6) . . ? C4 C5 C6 119.3(6) . . ? C4 C5 C10 120.7(6) . . ? C6 C5 C10 120.0(5) . . ? C7 C6 C5 121.9(5) . . ? C6 C7 C8 119.5(6) . . ? C9 C8 C7 122.0(6) . . ? C8 C9 N2 119.7(5) . . ? C8 C9 C10 119.4(5) . . ? N2 C9 C10 120.8(5) . . ? C5 C10 C1 117.1(5) . . ? C5 C10 C9 117.1(5) . . ? C1 C10 C9 125.8(5) . . ? N1 C11 C12 110.4(6) . . ? N1 C11 C13 111.3(6) . . ? C12 C11 C13 112.5(7) . . ? N2 C14 C16 113.0(5) . . ? N2 C14 C15 109.4(5) . . ? C16 C14 C15 112.1(5) . . ? N3 Sb2 N4 87.96(18) . . ? N3 Sb2 Cl2 96.14(13) . . ? N4 Sb2 Cl2 97.48(13) . . ? C17 N3 C27 119.7(4) . . ? C17 N3 Sb2 120.8(3) . . ? C27 N3 Sb2 115.3(3) . . ? C25 N4 C30 119.4(4) . . ? C25 N4 Sb2 121.5(3) . . ? C30 N4 Sb2 114.6(3) . . ? C18 C17 N3 119.6(5) . . ? C18 C17 C26 118.6(5) . . ? N3 C17 C26 121.8(5) . . ? C17 C18 C19 122.0(6) . . ? C20 C19 C18 121.0(6) . . ? C19 C20 C21 120.6(6) . . ? C22 C21 C26 121.3(5) . . ? C22 C21 C20 118.1(5) . . ? C26 C21 C20 120.5(6) . . ? C23 C22 C21 120.3(5) . . ? C22 C23 C24 120.4(6) . . ? C25 C24 C23 121.4(6) . . ? C24 C25 N4 119.0(5) . . ? C24 C25 C26 119.7(5) . . ? N4 C25 C26 121.2(5) . . ? C21 C26 C25 116.8(5) . . ? C21 C26 C17 117.2(5) . . ? C25 C26 C17 126.0(5) . . ? N3 C27 C29 112.7(5) . . ? N3 C27 C28 111.3(5) . . ? C29 C27 C28 110.3(5) . . ? N4 C30 C31 110.7(4) . . ? N4 C30 C32 111.7(5) . . ? C31 C30 C32 111.6(5) . . ? C34 C33 C38 120.0 . . ? C33 C34 C35 120.0 . . ? C34 C35 C36 120.0 . . ? C37 C36 C35 120.0 . . ? C38 C37 C36 120.0 . . ? C39 C38 C37 120.2(8) . . ? C39 C38 C33 119.7(8) . . ? C37 C38 C33 120.0 . . ? C41 C40 C45 120.0 . . ? C40 C41 C42 120.0 . . ? C41 C42 C43 120.0 . . ? C42 C43 C44 120.0 . . ? C45 C44 C43 120.0 . . ? C46 C45 C44 118.1(7) . . ? C46 C45 C40 121.8(7) . . ? C44 C45 C40 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Sb1 N1 C1 49.5(4) . . . . ? Cl1 Sb1 N1 C1 -46.9(4) . . . . ? N2 Sb1 N1 C11 -153.4(5) . . . . ? Cl1 Sb1 N1 C11 110.3(4) . . . . ? N1 Sb1 N2 C9 -51.2(4) . . . . ? Cl1 Sb1 N2 C9 45.3(4) . . . . ? N1 Sb1 N2 C14 155.9(4) . . . . ? Cl1 Sb1 N2 C14 -107.6(4) . . . . ? C11 N1 C1 C2 -6.5(9) . . . . ? Sb1 N1 C1 C2 149.4(5) . . . . ? C11 N1 C1 C10 171.2(6) . . . . ? Sb1 N1 C1 C10 -32.9(7) . . . . ? N1 C1 C2 C3 178.0(7) . . . . ? C10 C1 C2 C3 0.1(10) . . . . ? C1 C2 C3 C4 0.2(12) . . . . ? C2 C3 C4 C5 -0.4(11) . . . . ? C3 C4 C5 C6 -178.1(6) . . . . ? C3 C4 C5 C10 0.3(9) . . . . ? C4 C5 C6 C7 178.1(6) . . . . ? C10 C5 C6 C7 -0.3(9) . . . . ? C5 C6 C7 C8 1.2(9) . . . . ? C6 C7 C8 C9 -2.1(9) . . . . ? C7 C8 C9 N2 -175.3(5) . . . . ? C7 C8 C9 C10 2.1(8) . . . . ? C14 N2 C9 C8 5.5(7) . . . . ? Sb1 N2 C9 C8 -146.3(4) . . . . ? C14 N2 C9 C10 -171.9(5) . . . . ? Sb1 N2 C9 C10 36.3(6) . . . . ? C4 C5 C10 C1 0.1(8) . . . . ? C6 C5 C10 C1 178.4(5) . . . . ? C4 C5 C10 C9 -178.1(5) . . . . ? C6 C5 C10 C9 0.2(7) . . . . ? C2 C1 C10 C5 -0.2(8) . . . . ? N1 C1 C10 C5 -178.1(5) . . . . ? C2 C1 C10 C9 177.8(6) . . . . ? N1 C1 C10 C9 0.0(9) . . . . ? C8 C9 C10 C5 -1.1(7) . . . . ? N2 C9 C10 C5 176.2(5) . . . . ? C8 C9 C10 C1 -179.2(5) . . . . ? N2 C9 C10 C1 -1.8(8) . . . . ? C1 N1 C11 C12 -147.2(7) . . . . ? Sb1 N1 C11 C12 56.0(8) . . . . ? C1 N1 C11 C13 87.2(8) . . . . ? Sb1 N1 C11 C13 -69.7(7) . . . . ? C9 N2 C14 C16 -83.7(6) . . . . ? Sb1 N2 C14 C16 69.1(6) . . . . ? C9 N2 C14 C15 150.7(5) . . . . ? Sb1 N2 C14 C15 -56.5(6) . . . . ? N4 Sb2 N3 C17 44.6(4) . . . . ? Cl2 Sb2 N3 C17 -52.7(4) . . . . ? N4 Sb2 N3 C27 -158.5(4) . . . . ? Cl2 Sb2 N3 C27 104.2(4) . . . . ? N3 Sb2 N4 C25 -44.8(4) . . . . ? Cl2 Sb2 N4 C25 51.1(4) . . . . ? N3 Sb2 N4 C30 159.4(4) . . . . ? Cl2 Sb2 N4 C30 -104.7(3) . . . . ? C27 N3 C17 C18 -5.2(7) . . . . ? Sb2 N3 C17 C18 150.7(4) . . . . ? C27 N3 C17 C26 172.9(5) . . . . ? Sb2 N3 C17 C26 -31.3(6) . . . . ? N3 C17 C18 C19 177.3(5) . . . . ? C26 C17 C18 C19 -0.8(8) . . . . ? C17 C18 C19 C20 -0.1(10) . . . . ? C18 C19 C20 C21 1.1(10) . . . . ? C19 C20 C21 C22 -179.1(6) . . . . ? C19 C20 C21 C26 -1.1(9) . . . . ? C26 C21 C22 C23 -0.1(9) . . . . ? C20 C21 C22 C23 177.8(6) . . . . ? C21 C22 C23 C24 1.9(10) . . . . ? C22 C23 C24 C25 -2.8(10) . . . . ? C23 C24 C25 N4 -175.9(5) . . . . ? C23 C24 C25 C26 1.9(9) . . . . ? C30 N4 C25 C24 3.4(7) . . . . ? Sb2 N4 C25 C24 -151.3(4) . . . . ? C30 N4 C25 C26 -174.4(5) . . . . ? Sb2 N4 C25 C26 30.9(6) . . . . ? C22 C21 C26 C25 -0.8(7) . . . . ? C20 C21 C26 C25 -178.7(5) . . . . ? C22 C21 C26 C17 178.0(5) . . . . ? C20 C21 C26 C17 0.2(7) . . . . ? C24 C25 C26 C21 -0.1(7) . . . . ? N4 C25 C26 C21 177.6(4) . . . . ? C24 C25 C26 C17 -178.8(5) . . . . ? N4 C25 C26 C17 -1.1(8) . . . . ? C18 C17 C26 C21 0.7(7) . . . . ? N3 C17 C26 C21 -177.4(4) . . . . ? C18 C17 C26 C25 179.5(5) . . . . ? N3 C17 C26 C25 1.4(8) . . . . ? C17 N3 C27 C29 84.7(6) . . . . ? Sb2 N3 C27 C29 -72.4(5) . . . . ? C17 N3 C27 C28 -150.7(5) . . . . ? Sb2 N3 C27 C28 52.2(6) . . . . ? C25 N4 C30 C31 153.0(5) . . . . ? Sb2 N4 C30 C31 -50.6(6) . . . . ? C25 N4 C30 C32 -81.9(6) . . . . ? Sb2 N4 C30 C32 74.4(5) . . . . ? C38 C33 C34 C35 0.0 . . . . ? C33 C34 C35 C36 0.0 . . . . ? C34 C35 C36 C37 0.0 . . . . ? C35 C36 C37 C38 0.0 . . . . ? C36 C37 C38 C39 175.4(19) . . . . ? C36 C37 C38 C33 0.0 . . . . ? C34 C33 C38 C39 -175.4(19) . . . . ? C34 C33 C38 C37 0.0 . . . . ? C45 C40 C41 C42 0.0 . . . . ? C40 C41 C42 C43 0.0 . . . . ? C41 C42 C43 C44 0.0 . . . . ? C42 C43 C44 C45 0.0 . . . . ? C43 C44 C45 C46 177(2) . . . . ? C43 C44 C45 C40 0.0 . . . . ? C41 C40 C45 C46 -177(2) . . . . ? C41 C40 C45 C44 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.247 _refine_diff_density_min -1.038 _refine_diff_density_rms 0.121 # Attachment 'dr29.cif' data_dr29 _database_code_depnum_ccdc_archive 'CCDC 629188' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 As Cl N2' _chemical_formula_weight 350.71 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' As As 0.0499 2.0058 '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 8.8383(19) _cell_length_b 16.434(3) _cell_length_c 11.551(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.825(3) _cell_angle_gamma 90.00 _cell_volume 1606.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 417 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 26.47 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas n/a _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 2.275 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4631 _exptl_absorpt_correction_T_max 0.6001 _exptl_absorpt_process_details 'SADABS, Bruker (2000)' _exptl_special_details ; Data collection is performed with three batch runs at phi = 0.00 deg (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg (650 frames). A fourth batch run is collected at phi = 0.00 deg (50 frames) to monitor crystal and diffractometer stability. Frame width = 0.30 deg in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data. ; _diffrn_ambient_temperature 213(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_% <1 _diffrn_reflns_number 9898 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 26.47 _reflns_number_total 3256 _reflns_number_gt 2656 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker (2000)' _computing_cell_refinement 'SMART, Bruker (2000)' _computing_data_reduction 'XPREP, Bruker (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker (2000)' _computing_publication_material 'SHELXTL, Bruker (2000)' _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^)+(0.0344P)^2^+0.9209P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3256 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0763 _refine_ls_wR_factor_gt 0.0711 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.001 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 As1 As 0.30546(3) 0.098173(17) 0.62167(2) 0.03914(10) Uani 1 1 d . . . Cl1 Cl 0.35256(8) 0.17405(4) 0.79392(6) 0.04777(18) Uani 1 1 d . . . N1 N 0.4108(2) 0.15856(13) 0.53900(18) 0.0385(5) Uani 1 1 d . . . N2 N 0.4599(2) 0.02281(13) 0.67398(19) 0.0394(5) Uani 1 1 d . . . C1 C 0.5741(3) 0.17399(15) 0.5854(2) 0.0371(5) Uani 1 1 d . . . C2 C 0.6404(3) 0.24131(18) 0.5461(3) 0.0497(7) Uani 1 1 d . . . H2 H 0.5745 0.2773 0.4906 0.060 Uiso 1 1 calc R . . C3 C 0.8027(4) 0.25684(19) 0.5869(3) 0.0542(7) Uani 1 1 d . . . H3 H 0.8444 0.3027 0.5582 0.065 Uiso 1 1 calc R . . C4 C 0.9001(3) 0.2065(2) 0.6673(3) 0.0518(7) Uani 1 1 d . . . H4 H 1.0089 0.2179 0.6946 0.062 Uiso 1 1 calc R . . C5 C 0.8403(3) 0.13705(18) 0.7107(2) 0.0434(6) Uani 1 1 d . . . C6 C 0.9456(3) 0.0840(2) 0.7910(3) 0.0522(7) Uani 1 1 d . . . H6 H 1.0539 0.0966 0.8175 0.063 Uiso 1 1 calc R . . C7 C 0.8923(4) 0.0154(2) 0.8300(3) 0.0587(8) Uani 1 1 d . . . H7 H 0.9641 -0.0195 0.8831 0.070 Uiso 1 1 calc R . . C8 C 0.7309(3) -0.00443(18) 0.7923(3) 0.0515(7) Uani 1 1 d . . . H8 H 0.6965 -0.0525 0.8210 0.062 Uiso 1 1 calc R . . C9 C 0.6209(3) 0.04539(16) 0.7135(2) 0.0384(6) Uani 1 1 d . . . C10 C 0.6740(3) 0.11872(15) 0.6699(2) 0.0358(5) Uani 1 1 d . . . C11 C 0.3100(3) 0.21487(18) 0.4477(2) 0.0461(6) Uani 1 1 d . . . H11 H 0.3700 0.2299 0.3906 0.055 Uiso 1 1 calc R . . C12 C 0.2720(4) 0.29306(19) 0.5041(3) 0.0538(7) Uani 1 1 d . . . H12A H 0.3696 0.3192 0.5494 0.081 Uiso 1 1 calc R . . H12B H 0.2092 0.2805 0.5580 0.081 Uiso 1 1 calc R . . H12C H 0.2131 0.3293 0.4408 0.081 Uiso 1 1 calc R . . C13 C 0.1589(4) 0.1727(2) 0.3752(3) 0.0655(9) Uani 1 1 d . . . H13A H 0.1855 0.1231 0.3398 0.098 Uiso 1 1 calc R . . H13B H 0.0999 0.2086 0.3115 0.098 Uiso 1 1 calc R . . H13C H 0.0951 0.1594 0.4283 0.098 Uiso 1 1 calc R . . C14 C 0.4090(4) -0.05422(18) 0.7182(3) 0.0534(7) Uani 1 1 d . . . H14 H 0.4878 -0.0963 0.7150 0.064 Uiso 1 1 calc R . . C15 C 0.4063(5) -0.0478(2) 0.8497(3) 0.0719(10) Uani 1 1 d . . . H15A H 0.5091 -0.0303 0.9000 0.108 Uiso 1 1 calc R . . H15B H 0.3813 -0.1006 0.8771 0.108 Uiso 1 1 calc R . . H15C H 0.3267 -0.0086 0.8555 0.108 Uiso 1 1 calc R . . C16 C 0.2492(4) -0.0825(2) 0.6356(4) 0.0744(11) Uani 1 1 d . . . H16A H 0.2547 -0.0865 0.5531 0.112 Uiso 1 1 calc R . . H16B H 0.1682 -0.0436 0.6392 0.112 Uiso 1 1 calc R . . H16C H 0.2236 -0.1354 0.6622 0.112 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 As1 0.03004(14) 0.04300(17) 0.04432(15) -0.00587(12) 0.01065(10) -0.00611(11) Cl1 0.0423(3) 0.0533(4) 0.0515(4) -0.0145(3) 0.0195(3) -0.0048(3) N1 0.0352(11) 0.0397(12) 0.0399(11) 0.0022(9) 0.0099(9) 0.0032(9) N2 0.0412(11) 0.0334(11) 0.0468(12) -0.0023(9) 0.0180(9) -0.0042(9) C1 0.0397(13) 0.0367(14) 0.0387(13) -0.0023(11) 0.0175(10) -0.0004(11) C2 0.0505(16) 0.0479(17) 0.0550(16) 0.0086(13) 0.0220(13) 0.0009(13) C3 0.0595(18) 0.0480(18) 0.0640(18) 0.0006(14) 0.0320(15) -0.0123(14) C4 0.0376(14) 0.063(2) 0.0599(17) -0.0109(15) 0.0226(13) -0.0136(13) C5 0.0358(13) 0.0522(17) 0.0451(14) -0.0095(13) 0.0165(11) 0.0007(12) C6 0.0352(14) 0.064(2) 0.0555(17) -0.0062(15) 0.0103(12) 0.0053(13) C7 0.0492(17) 0.065(2) 0.0552(17) 0.0031(15) 0.0049(14) 0.0202(15) C8 0.0551(17) 0.0412(16) 0.0583(17) 0.0089(13) 0.0163(14) 0.0067(13) C9 0.0402(13) 0.0379(14) 0.0398(13) -0.0029(11) 0.0158(11) 0.0018(11) C10 0.0326(12) 0.0409(14) 0.0371(12) -0.0036(10) 0.0151(10) 0.0004(10) C11 0.0468(15) 0.0469(16) 0.0436(14) 0.0035(12) 0.0116(12) 0.0136(12) C12 0.0623(18) 0.0442(17) 0.0545(16) 0.0020(14) 0.0163(14) 0.0124(14) C13 0.0587(19) 0.063(2) 0.0581(18) -0.0067(15) -0.0090(15) 0.0143(16) C14 0.0623(18) 0.0356(16) 0.0732(19) -0.0034(14) 0.0369(16) -0.0070(13) C15 0.097(3) 0.057(2) 0.078(2) 0.0170(18) 0.051(2) -0.0013(19) C16 0.074(2) 0.051(2) 0.107(3) -0.021(2) 0.039(2) -0.0258(17) _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 As1 N2 1.812(2) . ? As1 N1 1.810(2) . ? As1 Cl1 2.2820(8) . ? N1 C1 1.410(3) . ? N1 C11 1.489(3) . ? N2 C9 1.413(3) . ? N2 C14 1.483(3) . ? C1 C2 1.389(4) . ? C1 C10 1.435(4) . ? C2 C3 1.398(4) . ? C3 C4 1.351(4) . ? C4 C5 1.409(4) . ? C5 C6 1.409(4) . ? C5 C10 1.439(3) . ? C6 C7 1.349(5) . ? C7 C8 1.404(4) . ? C8 C9 1.389(4) . ? C9 C10 1.436(4) . ? C11 C12 1.521(4) . ? C11 C13 1.523(4) . ? C14 C16 1.529(5) . ? C14 C15 1.531(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 As1 N1 95.61(9) . . ? N2 As1 Cl1 98.80(7) . . ? N1 As1 Cl1 99.70(7) . . ? C1 N1 C11 119.6(2) . . ? C1 N1 As1 121.62(16) . . ? C11 N1 As1 114.90(17) . . ? C9 N2 C14 119.4(2) . . ? C9 N2 As1 121.30(17) . . ? C14 N2 As1 115.07(17) . . ? C2 C1 N1 120.1(2) . . ? C2 C1 C10 119.5(2) . . ? N1 C1 C10 120.4(2) . . ? C1 C2 C3 121.6(3) . . ? C4 C3 C2 120.5(3) . . ? C3 C4 C5 120.7(3) . . ? C4 C5 C6 119.4(3) . . ? C4 C5 C10 120.4(2) . . ? C6 C5 C10 120.2(3) . . ? C7 C6 C5 120.6(3) . . ? C6 C7 C8 120.8(3) . . ? C9 C8 C7 121.4(3) . . ? C8 C9 N2 120.3(2) . . ? C8 C9 C10 119.1(2) . . ? N2 C9 C10 120.5(2) . . ? C9 C10 C5 117.9(2) . . ? C9 C10 C1 124.8(2) . . ? C5 C10 C1 117.3(2) . . ? N1 C11 C12 112.5(2) . . ? N1 C11 C13 110.8(2) . . ? C12 C11 C13 110.7(2) . . ? N2 C14 C16 111.2(3) . . ? N2 C14 C15 112.1(2) . . ? C16 C14 C15 111.3(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 N2 As1 N1 C1 -40.5(2) . . . . ? Cl1 As1 N1 C1 59.47(19) . . . . ? N2 As1 N1 C11 161.83(18) . . . . ? Cl1 As1 N1 C11 -98.22(17) . . . . ? N1 As1 N2 C9 40.4(2) . . . . ? Cl1 As1 N2 C9 -60.37(19) . . . . ? N1 As1 N2 C14 -162.93(19) . . . . ? Cl1 As1 N2 C14 96.32(18) . . . . ? C11 N1 C1 C2 0.0(4) . . . . ? As1 N1 C1 C2 -156.7(2) . . . . ? C11 N1 C1 C10 -177.6(2) . . . . ? As1 N1 C1 C10 25.7(3) . . . . ? N1 C1 C2 C3 -177.7(3) . . . . ? C10 C1 C2 C3 -0.1(4) . . . . ? C1 C2 C3 C4 -0.5(5) . . . . ? C2 C3 C4 C5 0.6(5) . . . . ? C3 C4 C5 C6 177.6(3) . . . . ? C3 C4 C5 C10 -0.1(4) . . . . ? C4 C5 C6 C7 -177.3(3) . . . . ? C10 C5 C6 C7 0.4(4) . . . . ? C5 C6 C7 C8 -0.5(5) . . . . ? C6 C7 C8 C9 0.3(5) . . . . ? C7 C8 C9 N2 178.0(3) . . . . ? C7 C8 C9 C10 0.0(4) . . . . ? C14 N2 C9 C8 0.5(4) . . . . ? As1 N2 C9 C8 156.2(2) . . . . ? C14 N2 C9 C10 178.5(2) . . . . ? As1 N2 C9 C10 -25.7(3) . . . . ? C8 C9 C10 C5 0.0(4) . . . . ? N2 C9 C10 C5 -178.1(2) . . . . ? C8 C9 C10 C1 177.8(2) . . . . ? N2 C9 C10 C1 -0.2(4) . . . . ? C4 C5 C10 C9 177.5(2) . . . . ? C6 C5 C10 C9 -0.1(4) . . . . ? C4 C5 C10 C1 -0.5(4) . . . . ? C6 C5 C10 C1 -178.1(2) . . . . ? C2 C1 C10 C9 -177.3(2) . . . . ? N1 C1 C10 C9 0.3(4) . . . . ? C2 C1 C10 C5 0.5(4) . . . . ? N1 C1 C10 C5 178.2(2) . . . . ? C1 N1 C11 C12 -77.4(3) . . . . ? As1 N1 C11 C12 80.7(3) . . . . ? C1 N1 C11 C13 158.1(2) . . . . ? As1 N1 C11 C13 -43.7(3) . . . . ? C9 N2 C14 C16 -160.5(2) . . . . ? As1 N2 C14 C16 42.3(3) . . . . ? C9 N2 C14 C15 74.2(3) . . . . ? As1 N2 C14 C15 -83.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.47 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.380 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.056 # Attachment 'dr38.cif' data_dr38 _database_code_depnum_ccdc_archive 'CCDC 629189' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17.75 H22 As Cl4 Ga N2' _chemical_formula_weight 549.81 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' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' As As 0.0499 2.0058 '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 7.233(2) _cell_length_b 17.314(6) _cell_length_c 19.580(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.501(6) _cell_angle_gamma 90.00 _cell_volume 2418.3(14) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 328 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 21.96 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas n/a _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1098 _exptl_absorpt_coefficient_mu 2.942 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5907 _exptl_absorpt_correction_T_max 0.9435 _exptl_absorpt_process_details 'SADABS, Bruker (2000)' _exptl_special_details ; Data collection is performed with three batch runs at phi = 0.00 deg (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg (650 frames). A fourth batch run is collected at phi = 0.00 deg (50 frames) to monitor crystal and diffractometer stability. Frame width = 0.30 deg in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data. ; _diffrn_ambient_temperature 198(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_% <1 _diffrn_reflns_number 13716 _diffrn_reflns_av_R_equivalents 0.1059 _diffrn_reflns_av_sigmaI/netI 0.0830 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 21.96 _reflns_number_total 2915 _reflns_number_gt 1858 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker (2000)' _computing_cell_refinement 'SMART, Bruker (2000)' _computing_data_reduction 'XPREP, Bruker (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker (2000)' _computing_publication_material 'SHELXTL, Bruker (2000)' _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^)+(0.0810P)^2^]' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2915 _refine_ls_number_parameters 233 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1085 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1550 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 As1 As 0.12674(15) 0.12442(5) 0.67040(5) 0.0482(4) Uani 1 1 d . . . N1 N 0.1930(9) 0.0264(4) 0.6716(4) 0.0392(19) Uani 1 1 d . . . N2 N 0.1362(10) 0.1497(4) 0.5841(4) 0.0419(19) Uani 1 1 d . . . C1 C 0.2421(11) -0.0158(5) 0.6140(5) 0.040(2) Uani 1 1 d . . . C2 C 0.3034(13) -0.0905(6) 0.6235(6) 0.053(3) Uani 1 1 d . . . H2A H 0.3214 -0.1117 0.6689 0.064 Uiso 1 1 calc R . . C3 C 0.3405(13) -0.1370(5) 0.5684(6) 0.053(3) Uani 1 1 d . . . H3A H 0.3755 -0.1896 0.5759 0.063 Uiso 1 1 calc R . . C4 C 0.3253(13) -0.1056(6) 0.5044(6) 0.054(3) Uani 1 1 d . . . H4A H 0.3521 -0.1365 0.4672 0.065 Uiso 1 1 calc R . . C5 C 0.2702(11) -0.0273(5) 0.4917(5) 0.045(3) Uani 1 1 d . . . C6 C 0.2542(12) 0.0044(6) 0.4244(6) 0.049(3) Uani 1 1 d . . . H6A H 0.2812 -0.0275 0.3878 0.059 Uiso 1 1 calc R . . C7 C 0.2039(12) 0.0755(6) 0.4107(5) 0.047(2) Uani 1 1 d . . . H7A H 0.1954 0.0945 0.3647 0.057 Uiso 1 1 calc R . . C8 C 0.1616(12) 0.1251(6) 0.4634(5) 0.047(2) Uani 1 1 d . . . H8A H 0.1233 0.1767 0.4526 0.057 Uiso 1 1 calc R . . C9 C 0.1760(12) 0.0984(5) 0.5309(5) 0.042(2) Uani 1 1 d . . . C10 C 0.2285(10) 0.0191(5) 0.5475(4) 0.030(2) Uani 1 1 d . . . C11 C 0.1986(14) -0.0130(6) 0.7390(5) 0.055(3) Uani 1 1 d . . . H11A H 0.1535 -0.0672 0.7294 0.066 Uiso 1 1 calc R . . C12 C 0.3976(16) -0.0172(7) 0.7776(6) 0.080(4) Uani 1 1 d . . . H12A H 0.4770 -0.0432 0.7487 0.120 Uiso 1 1 calc R . . H12B H 0.3998 -0.0462 0.8207 0.120 Uiso 1 1 calc R . . H12C H 0.4449 0.0352 0.7885 0.120 Uiso 1 1 calc R . . C13 C 0.0669(17) 0.0260(6) 0.7829(6) 0.079(4) Uani 1 1 d . . . H13A H -0.0608 0.0271 0.7567 0.118 Uiso 1 1 calc R . . H13B H 0.1095 0.0789 0.7940 0.118 Uiso 1 1 calc R . . H13C H 0.0681 -0.0033 0.8258 0.118 Uiso 1 1 calc R . . C14 C 0.1068(15) 0.2334(5) 0.5660(6) 0.056(3) Uani 1 1 d . . . H14A H 0.0197 0.2366 0.5208 0.067 Uiso 1 1 calc R . . C15 C 0.2914(16) 0.2711(6) 0.5567(6) 0.071(3) Uani 1 1 d . . . H15A H 0.3449 0.2435 0.5209 0.107 Uiso 1 1 calc R . . H15B H 0.3791 0.2690 0.6006 0.107 Uiso 1 1 calc R . . H15C H 0.2688 0.3251 0.5428 0.107 Uiso 1 1 calc R . . C16 C 0.014(2) 0.2748(6) 0.6203(7) 0.092(4) Uani 1 1 d . . . H16A H -0.1047 0.2494 0.6241 0.138 Uiso 1 1 calc R . . H16B H -0.0093 0.3288 0.6066 0.138 Uiso 1 1 calc R . . H16C H 0.0975 0.2728 0.6652 0.138 Uiso 1 1 calc R . . Ga1 Ga 0.63789(15) 0.23123(6) 0.77363(6) 0.0559(4) Uani 1 1 d . . . Cl1 Cl 0.6131(4) 0.14566(15) 0.69057(15) 0.0649(8) Uani 1 1 d . . . Cl2 Cl 0.6905(6) 0.34230(17) 0.73045(19) 0.1009(12) Uani 1 1 d . . . Cl3 Cl 0.3732(4) 0.23413(19) 0.8110(2) 0.0930(12) Uani 1 1 d . . . Cl4 Cl 0.8550(5) 0.1970(2) 0.85703(19) 0.1029(12) Uani 1 1 d . . . C17 C 0.604(3) 0.9595(13) 0.0076(15) 0.14(2) Uiso 0.25 1 d PG A -1 C18 C 0.461(3) 0.9434(12) 0.0449(13) 0.026(8) Uiso 0.25 1 d PGD A -1 H18A H 0.4688 0.8989 0.0736 0.031 Uiso 0.25 1 calc PR A -1 C19 C 0.308(3) 0.9924(15) 0.0402(13) 0.038(9) Uiso 0.25 1 d PG A -1 H19A H 0.2098 0.9814 0.0657 0.046 Uiso 0.25 1 calc PR A -1 C20 C 0.297(2) 1.0575(14) -0.0019(14) 0.103(19) Uiso 0.25 1 d PG A -1 H20A H 0.1915 1.0910 -0.0051 0.123 Uiso 0.25 1 calc PR A -1 C21 C 0.440(3) 1.0736(11) -0.0392(12) 0.026(8) Uiso 0.25 1 d PG A -1 H21A H 0.4324 1.1181 -0.0679 0.031 Uiso 0.25 1 calc PR A -1 C22 C 0.594(3) 1.0246(14) -0.0345(13) 0.029(8) Uiso 0.25 1 d PGD A -1 H22A H 0.6914 1.0357 -0.0600 0.035 Uiso 0.25 1 calc PR A -1 C23 C 0.783(10) 0.902(4) 0.012(4) 0.17(3) Uiso 0.25 1 d PD A -1 H23A H 0.7700 0.8596 0.0437 0.254 Uiso 0.25 1 calc PR A -1 H23B H 0.8985 0.9307 0.0285 0.254 Uiso 0.25 1 calc PR A -1 H23C H 0.7886 0.8811 -0.0343 0.254 Uiso 0.25 1 calc PR A -1 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 As1 0.0675(7) 0.0311(6) 0.0465(7) -0.0035(5) 0.0115(5) 0.0011(5) N1 0.054(5) 0.033(4) 0.031(4) 0.006(4) 0.008(4) 0.000(4) N2 0.055(5) 0.024(4) 0.046(5) 0.009(4) 0.006(4) 0.000(4) C1 0.034(5) 0.023(5) 0.062(7) 0.001(5) 0.004(5) 0.000(4) C2 0.055(6) 0.040(6) 0.066(7) 0.014(6) 0.013(5) -0.002(5) C3 0.052(6) 0.023(6) 0.082(9) -0.011(6) 0.007(6) 0.003(5) C4 0.042(6) 0.043(7) 0.078(9) -0.008(6) 0.009(6) 0.004(5) C5 0.027(5) 0.043(6) 0.066(8) -0.001(6) 0.009(5) -0.002(4) C6 0.049(6) 0.045(7) 0.055(7) -0.003(5) 0.012(5) -0.005(5) C7 0.048(6) 0.056(7) 0.039(6) -0.002(6) 0.009(5) -0.006(5) C8 0.044(6) 0.045(6) 0.053(7) 0.012(6) 0.011(5) -0.004(5) C9 0.038(5) 0.042(6) 0.045(6) -0.011(5) 0.000(5) -0.005(4) C10 0.023(5) 0.026(5) 0.039(6) -0.004(4) 0.000(4) -0.002(4) C11 0.069(7) 0.050(6) 0.045(7) 0.004(5) 0.011(6) -0.002(6) C12 0.113(10) 0.061(8) 0.053(8) 0.020(6) -0.024(7) -0.007(7) C13 0.131(10) 0.061(7) 0.053(7) -0.006(6) 0.042(7) -0.009(7) C14 0.071(7) 0.038(6) 0.057(7) 0.002(5) 0.003(6) 0.013(6) C15 0.096(9) 0.040(6) 0.073(9) 0.011(6) 0.002(7) -0.011(6) C16 0.149(12) 0.044(7) 0.088(10) -0.004(7) 0.032(9) 0.032(8) Ga1 0.0578(7) 0.0464(7) 0.0661(9) -0.0214(6) 0.0173(6) -0.0055(6) Cl1 0.0738(18) 0.0544(17) 0.0665(19) -0.0256(14) 0.0113(15) -0.0018(14) Cl2 0.162(3) 0.0493(18) 0.107(3) -0.0203(18) 0.069(3) -0.021(2) Cl3 0.073(2) 0.081(2) 0.136(3) -0.039(2) 0.053(2) -0.0070(17) Cl4 0.098(2) 0.104(3) 0.096(3) -0.040(2) -0.016(2) 0.007(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 As1 N1 1.762(7) . ? As1 N2 1.757(7) . ? N1 C1 1.437(11) . ? N1 C11 1.482(11) . ? N2 C9 1.434(11) . ? N2 C14 1.500(11) . ? C1 C2 1.371(12) . ? C1 C10 1.423(12) . ? C2 C3 1.408(14) . ? C3 C4 1.352(14) . ? C4 C5 1.423(13) . ? C5 C6 1.416(13) . ? C5 C10 1.429(12) . ? C6 C7 1.299(13) . ? C7 C8 1.414(13) . ? C8 C9 1.386(13) . ? C9 C10 1.447(12) . ? C11 C12 1.513(14) . ? C11 C13 1.539(13) . ? C14 C15 1.524(13) . ? C14 C16 1.526(14) . ? Ga1 Cl4 2.153(4) . ? Ga1 Cl2 2.160(3) . ? Ga1 Cl3 2.161(3) . ? Ga1 Cl1 2.185(3) . ? C17 C23 1.62(8) . ? C17 C18 1.3900 . ? C17 C22 1.3900 . ? C18 C19 1.3900 . ? C19 C20 1.3900 . ? C20 C21 1.3900 . ? C21 C22 1.3900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 As1 N2 101.4(3) . . ? C1 N1 C11 119.4(7) . . ? C1 N1 As1 125.5(6) . . ? C11 N1 As1 115.0(6) . . ? C9 N2 C14 117.6(7) . . ? C9 N2 As1 126.2(6) . . ? C14 N2 As1 116.2(6) . . ? C2 C1 N1 119.3(9) . . ? C2 C1 C10 119.9(9) . . ? N1 C1 C10 120.9(7) . . ? C1 C2 C3 122.2(10) . . ? C4 C3 C2 119.0(9) . . ? C3 C4 C5 121.5(10) . . ? C6 C5 C10 119.9(9) . . ? C6 C5 C4 120.7(10) . . ? C10 C5 C4 119.4(9) . . ? C7 C6 C5 122.5(10) . . ? C6 C7 C8 120.7(10) . . ? C9 C8 C7 120.2(9) . . ? C8 C9 N2 119.7(8) . . ? C8 C9 C10 120.4(9) . . ? N2 C9 C10 119.9(8) . . ? C5 C10 C1 117.9(8) . . ? C5 C10 C9 116.3(8) . . ? C1 C10 C9 125.8(8) . . ? N1 C11 C12 110.6(8) . . ? N1 C11 C13 111.5(8) . . ? C12 C11 C13 111.6(10) . . ? N2 C14 C15 110.5(8) . . ? N2 C14 C16 110.5(9) . . ? C15 C14 C16 112.0(10) . . ? Cl4 Ga1 Cl2 112.85(17) . . ? Cl4 Ga1 Cl3 108.99(17) . . ? Cl2 Ga1 Cl3 109.59(14) . . ? Cl4 Ga1 Cl1 109.74(13) . . ? Cl2 Ga1 Cl1 108.09(13) . . ? Cl3 Ga1 Cl1 107.44(12) . . ? C23 C17 C18 120.4(8) . . ? C23 C17 C22 119.6(8) . . ? C18 C17 C22 120.0 . . ? C19 C18 C17 120.0 . . ? C20 C19 C18 120.0 . . ? C19 C20 C21 120.0 . . ? C20 C21 C22 120.0 . . ? C21 C22 C17 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 As1 N1 C1 0.9(7) . . . . ? N2 As1 N1 C11 -179.9(6) . . . . ? N1 As1 N2 C9 3.8(7) . . . . ? N1 As1 N2 C14 -173.7(6) . . . . ? C11 N1 C1 C2 -3.6(12) . . . . ? As1 N1 C1 C2 175.6(6) . . . . ? C11 N1 C1 C10 176.6(7) . . . . ? As1 N1 C1 C10 -4.2(11) . . . . ? N1 C1 C2 C3 175.2(8) . . . . ? C10 C1 C2 C3 -5.0(13) . . . . ? C1 C2 C3 C4 3.8(14) . . . . ? C2 C3 C4 C5 -1.0(14) . . . . ? C3 C4 C5 C6 -179.7(9) . . . . ? C3 C4 C5 C10 -0.5(13) . . . . ? C10 C5 C6 C7 0.7(14) . . . . ? C4 C5 C6 C7 179.8(9) . . . . ? C5 C6 C7 C8 -0.2(14) . . . . ? C6 C7 C8 C9 0.9(13) . . . . ? C7 C8 C9 N2 178.8(8) . . . . ? C7 C8 C9 C10 -2.0(13) . . . . ? C14 N2 C9 C8 -8.5(12) . . . . ? As1 N2 C9 C8 174.0(6) . . . . ? C14 N2 C9 C10 172.4(8) . . . . ? As1 N2 C9 C10 -5.1(11) . . . . ? C6 C5 C10 C1 178.5(8) . . . . ? C4 C5 C10 C1 -0.7(12) . . . . ? C6 C5 C10 C9 -1.7(12) . . . . ? C4 C5 C10 C9 179.1(8) . . . . ? C2 C1 C10 C5 3.4(12) . . . . ? N1 C1 C10 C5 -176.8(7) . . . . ? C2 C1 C10 C9 -176.4(8) . . . . ? N1 C1 C10 C9 3.4(13) . . . . ? C8 C9 C10 C5 2.3(12) . . . . ? N2 C9 C10 C5 -178.5(7) . . . . ? C8 C9 C10 C1 -177.8(8) . . . . ? N2 C9 C10 C1 1.3(13) . . . . ? C1 N1 C11 C12 79.9(11) . . . . ? As1 N1 C11 C12 -99.4(8) . . . . ? C1 N1 C11 C13 -155.3(8) . . . . ? As1 N1 C11 C13 25.4(10) . . . . ? C9 N2 C14 C15 -71.1(10) . . . . ? As1 N2 C14 C15 106.6(8) . . . . ? C9 N2 C14 C16 164.3(9) . . . . ? As1 N2 C14 C16 -17.9(11) . . . . ? C23 C17 C18 C19 -179(4) . . . . ? C22 C17 C18 C19 0.0 . . . . ? C17 C18 C19 C20 0.0 . . . . ? C18 C19 C20 C21 0.0 . . . . ? C19 C20 C21 C22 0.0 . . . . ? C20 C21 C22 C17 0.0 . . . . ? C23 C17 C22 C21 179(4) . . . . ? C18 C17 C22 C21 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 21.96 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.875 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.112 # Attachment 'dr69.cif' data_dr69 _database_code_depnum_ccdc_archive 'CCDC 629190' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H54 F6 N6 O6 S2 Sb2' _chemical_formula_weight 1112.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5648(13) _cell_length_b 9.7606(15) _cell_length_c 27.018(4) _cell_angle_alpha 81.973(2) _cell_angle_beta 89.580(2) _cell_angle_gamma 81.727(2) _cell_volume 2213.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 884 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 24.79 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas n/a _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 1.391 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7683 _exptl_absorpt_correction_T_max 0.8734 _exptl_absorpt_process_details 'SADABS, Bruker (2000)' _exptl_special_details ; Data collection is performed with four batch runs at phi = 0.00 deg (650 frames), at phi = 90.00 deg (650 frames), at phi = 180.00 deg (650 frames), and at phi = 270.00 deg (650 frames). A fifth batch run is collected at phi = 0.00 deg (50 frames) to monitor crystal and diffractometer stability. Frame width = 0.30 deg in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data. ; _diffrn_ambient_temperature 203(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_% <1 _diffrn_reflns_number 20501 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 24.80 _reflns_number_total 7522 _reflns_number_gt 5704 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker (2000)' _computing_cell_refinement 'SMART, Bruker (2000)' _computing_data_reduction 'XPREP, Bruker (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker (2000)' _computing_publication_material 'SHELXTL, Bruker (2000)' _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^)+(0.0447P)^2^+2.6353P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7522 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.001 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 0.55672(4) -0.00416(3) 0.407436(11) 0.02871(10) Uani 1 1 d . . . N1 N 0.5718(4) -0.1009(4) 0.34666(14) 0.0271(9) Uani 1 1 d . . . N2 N 0.4112(4) 0.1600(4) 0.37364(14) 0.0256(8) Uani 1 1 d . . . N3 N 0.7779(4) 0.1029(4) 0.38601(15) 0.0308(9) Uani 1 1 d . . . H3B H 0.8418 0.0839 0.4141 0.037 Uiso 1 1 calc R . . C1 C 0.5539(5) -0.0277(5) 0.29715(17) 0.0265(10) Uani 1 1 d . . . C2 C 0.6126(6) -0.0969(5) 0.25805(18) 0.0362(12) Uani 1 1 d . . . H2A H 0.6568 -0.1915 0.2653 0.043 Uiso 1 1 calc R . . C3 C 0.6094(6) -0.0340(6) 0.20885(19) 0.0429(14) Uani 1 1 d . . . H3A H 0.6523 -0.0848 0.1836 0.051 Uiso 1 1 calc R . . C4 C 0.5440(6) 0.1013(6) 0.19730(19) 0.0427(13) Uani 1 1 d . . . H4A H 0.5419 0.1443 0.1639 0.051 Uiso 1 1 calc R . . C5 C 0.4791(6) 0.1785(5) 0.23474(18) 0.0321(11) Uani 1 1 d . . . C6 C 0.4819(5) 0.1165(5) 0.28637(17) 0.0272(10) Uani 1 1 d . . . C7 C 0.4092(6) 0.3187(6) 0.2197(2) 0.0446(14) Uani 1 1 d . . . H7A H 0.4081 0.3568 0.1858 0.053 Uiso 1 1 calc R . . C8 C 0.3440(7) 0.3983(6) 0.2537(2) 0.0458(14) Uani 1 1 d . . . H8A H 0.2976 0.4911 0.2435 0.055 Uiso 1 1 calc R . . C9 C 0.3458(6) 0.3420(5) 0.30442(19) 0.0372(12) Uani 1 1 d . . . H9A H 0.3006 0.3991 0.3276 0.045 Uiso 1 1 calc R . . C10 C 0.4115(5) 0.2056(5) 0.32191(17) 0.0269(10) Uani 1 1 d . . . C11 C 0.6426(6) -0.2506(5) 0.35385(19) 0.0337(11) Uani 1 1 d . . . H11A H 0.7337 -0.2609 0.3313 0.040 Uiso 1 1 calc R . . C12 C 0.5255(6) -0.3426(5) 0.3396(2) 0.0437(13) Uani 1 1 d . . . H12A H 0.4875 -0.3097 0.3057 0.066 Uiso 1 1 calc R . . H12B H 0.4373 -0.3382 0.3623 0.066 Uiso 1 1 calc R . . H12C H 0.5773 -0.4384 0.3417 0.066 Uiso 1 1 calc R . . C13 C 0.7019(7) -0.3036(5) 0.4066(2) 0.0429(13) Uani 1 1 d . . . H13A H 0.7771 -0.2460 0.4159 0.064 Uiso 1 1 calc R . . H13B H 0.7528 -0.3996 0.4084 0.064 Uiso 1 1 calc R . . H13C H 0.6138 -0.2993 0.4294 0.064 Uiso 1 1 calc R . . C14 C 0.3209(5) 0.2532(5) 0.40635(17) 0.0286(10) Uani 1 1 d . . . H14A H 0.3486 0.3484 0.3970 0.034 Uiso 1 1 calc R . . C15 C 0.1440(6) 0.2611(6) 0.3983(2) 0.0411(13) Uani 1 1 d . . . H15A H 0.1181 0.2899 0.3632 0.062 Uiso 1 1 calc R . . H15B H 0.0882 0.3285 0.4178 0.062 Uiso 1 1 calc R . . H15C H 0.1129 0.1699 0.4089 0.062 Uiso 1 1 calc R . . C16 C 0.3594(6) 0.2091(6) 0.46114(18) 0.0410(13) Uani 1 1 d . . . H16A H 0.4720 0.2040 0.4666 0.061 Uiso 1 1 calc R . . H16B H 0.3279 0.1181 0.4717 0.061 Uiso 1 1 calc R . . H16C H 0.3030 0.2769 0.4804 0.061 Uiso 1 1 calc R . . C17 C 0.8746(6) 0.0467(7) 0.3459(2) 0.0511(15) Uani 1 1 d . . . H17A H 0.9640 0.0971 0.3396 0.077 Uiso 1 1 calc R . . H17B H 0.8111 0.0579 0.3156 0.077 Uiso 1 1 calc R . . H17C H 0.9121 -0.0517 0.3561 0.077 Uiso 1 1 calc R . . C18 C 0.7403(6) 0.2570(5) 0.3764(2) 0.0475(14) Uani 1 1 d . . . H18A H 0.8359 0.2969 0.3677 0.071 Uiso 1 1 calc R . . H18B H 0.6956 0.2916 0.4061 0.071 Uiso 1 1 calc R . . H18C H 0.6647 0.2836 0.3489 0.071 Uiso 1 1 calc R . . S1 S 0.17509(15) 0.83754(13) 0.46167(5) 0.0344(3) Uani 1 1 d . . . O1 O 0.2809(5) 0.8685(4) 0.42151(15) 0.0541(10) Uani 1 1 d . . . O2 O 0.0121(4) 0.8795(4) 0.44984(16) 0.0586(11) Uani 1 1 d . . . O3 O 0.2267(5) 0.8665(4) 0.50877(14) 0.0526(10) Uani 1 1 d . . . C19 C 0.1965(7) 0.6477(6) 0.4700(2) 0.0464(14) Uani 1 1 d . . . F1 F 0.1535(5) 0.6018(4) 0.42869(15) 0.0751(11) Uani 1 1 d . . . F2 F 0.3448(5) 0.5913(4) 0.48018(17) 0.0826(13) Uani 1 1 d . . . F3 F 0.1100(5) 0.5982(4) 0.50709(15) 0.0819(12) Uani 1 1 d . . . Sb2 Sb 0.04668(4) 0.92293(3) 0.093770(13) 0.03742(11) Uani 1 1 d . . . N4 N 0.0715(5) 0.9687(4) 0.16245(16) 0.0372(10) Uani 1 1 d . . . N5 N -0.0695(5) 0.7641(4) 0.11766(16) 0.0371(10) Uani 1 1 d . . . N6 N 0.2933(5) 0.7891(4) 0.09741(16) 0.0415(11) Uani 1 1 d . . . H6A H 0.3056 0.7534 0.0676 0.050 Uiso 1 1 calc R . . C20 C 0.0740(6) 0.8704(5) 0.20604(19) 0.0363(12) Uani 1 1 d . . . C21 C 0.1529(6) 0.8940(6) 0.2480(2) 0.0485(14) Uani 1 1 d . . . H21A H 0.2114 0.9691 0.2453 0.058 Uiso 1 1 calc R . . C22 C 0.1482(7) 0.8094(8) 0.2944(2) 0.0601(18) Uani 1 1 d . . . H22A H 0.2021 0.8287 0.3222 0.072 Uiso 1 1 calc R . . C23 C 0.0654(7) 0.6994(7) 0.2989(2) 0.0566(18) Uani 1 1 d . . . H23A H 0.0609 0.6443 0.3302 0.068 Uiso 1 1 calc R . . C24 C -0.0136(7) 0.6669(6) 0.2577(2) 0.0447(14) Uani 1 1 d . . . C25 C -0.0060(6) 0.7494(5) 0.20896(18) 0.0349(12) Uani 1 1 d . . . C26 C -0.1026(8) 0.5564(6) 0.2651(2) 0.0555(17) Uani 1 1 d . . . H26A H -0.1074 0.5059 0.2972 0.067 Uiso 1 1 calc R . . C27 C -0.1811(8) 0.5217(6) 0.2271(3) 0.064(2) Uani 1 1 d . . . H27A H -0.2433 0.4493 0.2328 0.077 Uiso 1 1 calc R . . C28 C -0.1706(7) 0.5940(6) 0.1782(2) 0.0506(15) Uani 1 1 d . . . H28A H -0.2247 0.5671 0.1518 0.061 Uiso 1 1 calc R . . C29 C -0.0828(6) 0.7034(5) 0.16811(19) 0.0374(12) Uani 1 1 d . . . C30 C 0.1082(7) 1.1103(5) 0.1677(2) 0.0467(14) Uani 1 1 d . . . H30A H 0.2090 1.0989 0.1865 0.056 Uiso 1 1 calc R . . C31 C -0.0187(8) 1.1866(7) 0.1974(3) 0.0665(19) Uani 1 1 d . . . H31A H -0.0290 1.1313 0.2296 0.100 Uiso 1 1 calc R . . H31B H -0.1184 1.2009 0.1793 0.100 Uiso 1 1 calc R . . H31C H 0.0100 1.2765 0.2022 0.100 Uiso 1 1 calc R . . C32 C 0.1280(8) 1.1969(6) 0.1175(3) 0.0629(18) Uani 1 1 d . . . H32A H 0.2100 1.1477 0.0989 0.094 Uiso 1 1 calc R . . H32B H 0.1572 1.2863 0.1227 0.094 Uiso 1 1 calc R . . H32C H 0.0294 1.2121 0.0987 0.094 Uiso 1 1 calc R . . C33 C -0.1366(6) 0.6978(5) 0.0771(2) 0.0415(13) Uani 1 1 d . . . H33A H -0.2388 0.6702 0.0890 0.050 Uiso 1 1 calc R . . C34 C -0.0287(7) 0.5656(6) 0.0689(2) 0.0588(17) Uani 1 1 d . . . H34A H -0.0117 0.5036 0.1003 0.088 Uiso 1 1 calc R . . H34B H 0.0717 0.5895 0.0563 0.088 Uiso 1 1 calc R . . H34C H -0.0771 0.5191 0.0448 0.088 Uiso 1 1 calc R . . C35 C -0.1688(8) 0.7973(7) 0.0287(2) 0.0569(16) Uani 1 1 d . . . H35A H -0.2395 0.8798 0.0350 0.085 Uiso 1 1 calc R . . H35B H -0.2171 0.7512 0.0045 0.085 Uiso 1 1 calc R . . H35C H -0.0703 0.8245 0.0157 0.085 Uiso 1 1 calc R . . C36 C 0.3237(8) 0.6699(7) 0.1369(2) 0.0658(19) Uani 1 1 d . . . H36A H 0.4303 0.6227 0.1341 0.099 Uiso 1 1 calc R . . H36B H 0.2493 0.6055 0.1337 0.099 Uiso 1 1 calc R . . H36C H 0.3116 0.7025 0.1693 0.099 Uiso 1 1 calc R . . C37 C 0.4116(7) 0.8859(7) 0.0980(3) 0.0669(19) Uani 1 1 d . . . H37A H 0.5168 0.8332 0.0993 0.100 Uiso 1 1 calc R . . H37B H 0.3958 0.9340 0.1271 0.100 Uiso 1 1 calc R . . H37C H 0.3994 0.9538 0.0679 0.100 Uiso 1 1 calc R . . S4 S 0.66751(18) 0.20211(16) 0.04259(6) 0.0496(4) Uani 1 1 d . . . O4 O 0.7980(7) 0.2312(6) 0.0130(2) 0.1018(19) Uani 1 1 d . . . O5 O 0.7124(7) 0.0979(5) 0.08481(18) 0.0923(18) Uani 1 1 d . . . O6 O 0.5407(7) 0.1834(7) 0.0139(3) 0.134(3) Uani 1 1 d . . . C38 C 0.6018(8) 0.3615(6) 0.0687(2) 0.0555(16) Uani 1 1 d . . . F4 F 0.6111(5) 0.4752(4) 0.03711(17) 0.0900(13) Uani 1 1 d . . . F5 F 0.6843(6) 0.3703(4) 0.10895(15) 0.0855(13) Uani 1 1 d . . . F6 F 0.4526(5) 0.3654(5) 0.08284(19) 0.1003(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb1 0.0352(2) 0.02584(18) 0.02363(18) -0.00247(13) -0.00217(13) -0.00040(13) N1 0.032(2) 0.021(2) 0.027(2) -0.0073(16) -0.0016(17) 0.0018(16) N2 0.026(2) 0.025(2) 0.026(2) -0.0070(16) 0.0004(16) -0.0006(16) N3 0.028(2) 0.032(2) 0.032(2) -0.0085(18) -0.0072(17) 0.0010(17) C1 0.022(2) 0.031(3) 0.027(3) -0.007(2) -0.0023(19) -0.0036(19) C2 0.041(3) 0.033(3) 0.033(3) -0.013(2) -0.008(2) 0.007(2) C3 0.042(3) 0.055(4) 0.031(3) -0.019(3) 0.000(2) 0.010(3) C4 0.052(3) 0.052(4) 0.022(3) -0.004(2) 0.000(2) 0.001(3) C5 0.031(3) 0.037(3) 0.027(3) -0.004(2) -0.002(2) -0.003(2) C6 0.029(3) 0.026(2) 0.026(3) -0.0052(19) 0.000(2) -0.0020(19) C7 0.050(3) 0.045(3) 0.034(3) -0.002(2) 0.001(3) 0.003(3) C8 0.062(4) 0.031(3) 0.037(3) 0.003(2) 0.001(3) 0.009(3) C9 0.045(3) 0.032(3) 0.033(3) -0.008(2) 0.002(2) 0.004(2) C10 0.025(2) 0.031(3) 0.025(3) -0.004(2) -0.0004(19) -0.0049(19) C11 0.036(3) 0.026(3) 0.038(3) -0.005(2) -0.002(2) 0.003(2) C12 0.046(3) 0.028(3) 0.057(4) -0.010(3) 0.001(3) -0.002(2) C13 0.050(3) 0.034(3) 0.041(3) 0.000(2) -0.008(3) 0.006(2) C14 0.030(3) 0.028(3) 0.029(3) -0.006(2) 0.000(2) -0.005(2) C15 0.028(3) 0.046(3) 0.052(3) -0.019(3) 0.001(2) -0.002(2) C16 0.047(3) 0.047(3) 0.030(3) -0.014(2) 0.001(2) -0.001(2) C17 0.038(3) 0.073(4) 0.050(4) -0.026(3) 0.004(3) -0.016(3) C18 0.033(3) 0.033(3) 0.075(4) 0.002(3) -0.007(3) -0.008(2) S1 0.0354(7) 0.0321(7) 0.0367(7) -0.0086(5) -0.0037(6) -0.0041(5) O1 0.063(3) 0.051(2) 0.052(3) -0.0041(19) 0.015(2) -0.027(2) O2 0.043(2) 0.054(3) 0.075(3) -0.015(2) -0.016(2) 0.0094(19) O3 0.058(3) 0.057(3) 0.046(2) -0.0244(19) -0.0110(19) -0.0022(19) C19 0.057(4) 0.038(3) 0.045(3) -0.002(3) 0.001(3) -0.011(3) F1 0.114(3) 0.049(2) 0.071(3) -0.0288(19) -0.006(2) -0.022(2) F2 0.065(3) 0.046(2) 0.129(4) -0.008(2) -0.015(2) 0.0158(18) F3 0.104(3) 0.066(3) 0.078(3) 0.009(2) 0.027(2) -0.038(2) Sb2 0.0455(2) 0.0312(2) 0.0339(2) 0.00094(15) -0.00251(16) -0.00524(16) N4 0.040(2) 0.033(2) 0.039(3) -0.0101(19) -0.003(2) -0.0029(19) N5 0.044(3) 0.030(2) 0.037(2) -0.0064(19) 0.003(2) -0.0062(19) N6 0.044(3) 0.045(3) 0.035(3) -0.010(2) 0.010(2) -0.002(2) C20 0.035(3) 0.034(3) 0.036(3) -0.008(2) -0.002(2) 0.009(2) C21 0.036(3) 0.057(4) 0.051(4) -0.016(3) -0.007(3) 0.009(3) C22 0.046(4) 0.085(5) 0.041(4) -0.011(3) -0.009(3) 0.024(4) C23 0.056(4) 0.071(5) 0.030(3) -0.002(3) 0.002(3) 0.028(3) C24 0.047(3) 0.040(3) 0.037(3) 0.003(2) 0.012(3) 0.018(3) C25 0.035(3) 0.032(3) 0.034(3) -0.005(2) 0.006(2) 0.011(2) C26 0.073(4) 0.043(4) 0.041(4) 0.004(3) 0.020(3) 0.015(3) C27 0.085(5) 0.030(3) 0.073(5) -0.002(3) 0.040(4) -0.002(3) C28 0.066(4) 0.035(3) 0.052(4) -0.007(3) 0.015(3) -0.012(3) C29 0.043(3) 0.026(3) 0.039(3) -0.005(2) 0.009(2) 0.005(2) C30 0.043(3) 0.035(3) 0.063(4) -0.015(3) -0.009(3) 0.000(2) C31 0.062(4) 0.053(4) 0.088(5) -0.035(4) -0.004(4) 0.005(3) C32 0.065(4) 0.033(3) 0.093(5) -0.006(3) -0.009(4) -0.014(3) C33 0.045(3) 0.045(3) 0.039(3) -0.015(3) 0.008(3) -0.012(3) C34 0.067(4) 0.049(4) 0.067(4) -0.030(3) 0.011(3) -0.010(3) C35 0.066(4) 0.067(4) 0.042(3) -0.014(3) -0.009(3) -0.017(3) C36 0.062(4) 0.064(4) 0.058(4) 0.009(3) 0.014(3) 0.019(3) C37 0.036(3) 0.075(5) 0.094(5) -0.029(4) 0.008(3) -0.007(3) S4 0.0524(9) 0.0560(9) 0.0420(8) -0.0094(7) 0.0034(7) -0.0112(7) O4 0.093(4) 0.116(5) 0.094(4) -0.012(3) 0.044(3) -0.013(3) O5 0.146(5) 0.063(3) 0.061(3) -0.007(3) 0.025(3) 0.006(3) O6 0.102(5) 0.136(6) 0.180(7) -0.098(5) -0.061(5) 0.012(4) C38 0.063(4) 0.050(4) 0.054(4) -0.001(3) -0.007(3) -0.013(3) F4 0.115(4) 0.057(3) 0.090(3) 0.013(2) -0.025(3) -0.009(2) F5 0.134(4) 0.059(2) 0.067(3) -0.011(2) -0.040(3) -0.019(2) F6 0.071(3) 0.114(4) 0.123(4) -0.051(3) 0.028(3) -0.004(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 N2 1.997(4) . ? Sb1 N1 2.000(4) . ? Sb1 N3 2.323(4) . ? N1 C1 1.424(6) . ? N1 C11 1.486(6) . ? N2 C10 1.407(6) . ? N2 C14 1.490(6) . ? N3 C17 1.478(6) . ? N3 C18 1.479(6) . ? C1 C2 1.385(6) . ? C1 C6 1.444(6) . ? C2 C3 1.383(7) . ? C3 C4 1.352(7) . ? C4 C5 1.409(7) . ? C5 C7 1.417(7) . ? C5 C6 1.440(6) . ? C6 C10 1.455(6) . ? C7 C8 1.352(7) . ? C8 C9 1.402(7) . ? C9 C10 1.387(7) . ? C11 C13 1.512(7) . ? C11 C12 1.523(7) . ? C14 C16 1.508(7) . ? C14 C15 1.522(6) . ? S1 O2 1.423(4) . ? S1 O3 1.428(4) . ? S1 O1 1.436(4) . ? S1 C19 1.817(6) . ? C19 F3 1.320(6) . ? C19 F2 1.324(7) . ? C19 F1 1.333(6) . ? Sb2 N4 1.988(4) . ? Sb2 N5 1.991(4) . ? Sb2 N6 2.313(4) . ? N4 C20 1.410(6) . ? N4 C30 1.487(7) . ? N5 C29 1.419(6) . ? N5 C33 1.505(7) . ? N6 C36 1.460(7) . ? N6 C37 1.482(7) . ? C20 C21 1.386(7) . ? C20 C25 1.441(7) . ? C21 C22 1.406(8) . ? C22 C23 1.360(9) . ? C23 C24 1.404(9) . ? C24 C26 1.400(9) . ? C24 C25 1.449(7) . ? C25 C29 1.444(7) . ? C26 C27 1.339(9) . ? C27 C28 1.416(8) . ? C28 C29 1.388(7) . ? C30 C31 1.517(8) . ? C30 C32 1.517(8) . ? C33 C35 1.517(8) . ? C33 C34 1.517(7) . ? S4 O6 1.387(6) . ? S4 O4 1.408(5) . ? S4 O5 1.433(5) . ? S4 C38 1.813(7) . ? C38 F4 1.314(7) . ? C38 F5 1.320(7) . ? C38 F6 1.328(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Sb1 N1 93.00(15) . . ? N2 Sb1 N3 92.22(14) . . ? N1 Sb1 N3 92.66(14) . . ? C1 N1 C11 118.7(4) . . ? C1 N1 Sb1 122.9(3) . . ? C11 N1 Sb1 116.7(3) . . ? C10 N2 C14 118.4(4) . . ? C10 N2 Sb1 123.5(3) . . ? C14 N2 Sb1 117.0(3) . . ? C17 N3 C18 111.8(4) . . ? C17 N3 Sb1 115.3(3) . . ? C18 N3 Sb1 112.5(3) . . ? C2 C1 N1 118.4(4) . . ? C2 C1 C6 118.9(4) . . ? N1 C1 C6 122.7(4) . . ? C3 C2 C1 123.3(5) . . ? C4 C3 C2 119.5(5) . . ? C3 C4 C5 120.8(5) . . ? C7 C5 C4 117.7(5) . . ? C7 C5 C6 121.2(4) . . ? C4 C5 C6 121.1(4) . . ? C5 C6 C1 116.3(4) . . ? C5 C6 C10 116.5(4) . . ? C1 C6 C10 127.1(4) . . ? C8 C7 C5 120.7(5) . . ? C7 C8 C9 119.8(5) . . ? C10 C9 C8 122.9(5) . . ? C9 C10 N2 118.6(4) . . ? C9 C10 C6 119.0(4) . . ? N2 C10 C6 122.5(4) . . ? N1 C11 C13 113.4(4) . . ? N1 C11 C12 111.1(4) . . ? C13 C11 C12 108.9(4) . . ? N2 C14 C16 113.1(4) . . ? N2 C14 C15 111.1(4) . . ? C16 C14 C15 108.9(4) . . ? O2 S1 O3 116.0(2) . . ? O2 S1 O1 115.2(3) . . ? O3 S1 O1 113.7(3) . . ? O2 S1 C19 103.7(3) . . ? O3 S1 C19 103.0(3) . . ? O1 S1 C19 102.9(2) . . ? F3 C19 F2 107.2(5) . . ? F3 C19 F1 107.9(5) . . ? F2 C19 F1 107.2(5) . . ? F3 C19 S1 111.9(4) . . ? F2 C19 S1 111.3(4) . . ? F1 C19 S1 111.0(4) . . ? N4 Sb2 N5 92.77(17) . . ? N4 Sb2 N6 91.98(16) . . ? N5 Sb2 N6 95.34(16) . . ? C20 N4 C30 117.9(4) . . ? C20 N4 Sb2 123.8(3) . . ? C30 N4 Sb2 117.9(3) . . ? C29 N5 C33 118.6(4) . . ? C29 N5 Sb2 126.1(3) . . ? C33 N5 Sb2 115.1(3) . . ? C36 N6 C37 111.9(5) . . ? C36 N6 Sb2 117.8(3) . . ? C37 N6 Sb2 107.2(3) . . ? C21 C20 N4 118.3(5) . . ? C21 C20 C25 119.2(5) . . ? N4 C20 C25 122.5(5) . . ? C20 C21 C22 122.1(6) . . ? C23 C22 C21 119.8(6) . . ? C22 C23 C24 121.1(6) . . ? C26 C24 C23 118.5(6) . . ? C26 C24 C25 121.2(6) . . ? C23 C24 C25 120.2(6) . . ? C29 C25 C20 126.3(4) . . ? C29 C25 C24 116.4(5) . . ? C20 C25 C24 117.2(5) . . ? C27 C26 C24 120.9(6) . . ? C26 C27 C28 120.1(6) . . ? C29 C28 C27 122.0(6) . . ? C28 C29 N5 118.5(5) . . ? C28 C29 C25 119.1(5) . . ? N5 C29 C25 122.4(5) . . ? N4 C30 C31 110.5(5) . . ? N4 C30 C32 112.2(5) . . ? C31 C30 C32 110.1(5) . . ? N5 C33 C35 112.8(4) . . ? N5 C33 C34 109.9(5) . . ? C35 C33 C34 111.4(5) . . ? O6 S4 O4 112.0(5) . . ? O6 S4 O5 116.8(4) . . ? O4 S4 O5 111.9(4) . . ? O6 S4 C38 104.7(3) . . ? O4 S4 C38 105.0(3) . . ? O5 S4 C38 105.2(3) . . ? F4 C38 F5 107.1(5) . . ? F4 C38 F6 107.6(6) . . ? F5 C38 F6 106.4(6) . . ? F4 C38 S4 113.1(5) . . ? F5 C38 S4 112.0(4) . . ? F6 C38 S4 110.3(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 N2 Sb1 N1 C1 28.3(3) . . . . ? N3 Sb1 N1 C1 -64.0(3) . . . . ? N2 Sb1 N1 C11 -166.8(3) . . . . ? N3 Sb1 N1 C11 100.8(3) . . . . ? N1 Sb1 N2 C10 -29.2(4) . . . . ? N3 Sb1 N2 C10 63.6(4) . . . . ? N1 Sb1 N2 C14 162.9(3) . . . . ? N3 Sb1 N2 C14 -104.3(3) . . . . ? N2 Sb1 N3 C17 -106.4(4) . . . . ? N1 Sb1 N3 C17 -13.3(4) . . . . ? N2 Sb1 N3 C18 23.4(4) . . . . ? N1 Sb1 N3 C18 116.5(4) . . . . ? C11 N1 C1 C2 -4.1(6) . . . . ? Sb1 N1 C1 C2 160.5(3) . . . . ? C11 N1 C1 C6 177.9(4) . . . . ? Sb1 N1 C1 C6 -17.5(6) . . . . ? N1 C1 C2 C3 -176.4(5) . . . . ? C6 C1 C2 C3 1.6(7) . . . . ? C1 C2 C3 C4 -1.1(8) . . . . ? C2 C3 C4 C5 -0.1(8) . . . . ? C3 C4 C5 C7 -178.5(5) . . . . ? C3 C4 C5 C6 0.7(8) . . . . ? C7 C5 C6 C1 179.0(5) . . . . ? C4 C5 C6 C1 -0.2(7) . . . . ? C7 C5 C6 C10 -0.8(7) . . . . ? C4 C5 C6 C10 180.0(4) . . . . ? C2 C1 C6 C5 -0.9(6) . . . . ? N1 C1 C6 C5 177.0(4) . . . . ? C2 C1 C6 C10 178.9(5) . . . . ? N1 C1 C6 C10 -3.2(7) . . . . ? C4 C5 C7 C8 179.7(5) . . . . ? C6 C5 C7 C8 0.4(8) . . . . ? C5 C7 C8 C9 0.2(9) . . . . ? C7 C8 C9 C10 -0.4(9) . . . . ? C8 C9 C10 N2 178.4(5) . . . . ? C8 C9 C10 C6 0.0(8) . . . . ? C14 N2 C10 C9 8.4(6) . . . . ? Sb1 N2 C10 C9 -159.4(4) . . . . ? C14 N2 C10 C6 -173.3(4) . . . . ? Sb1 N2 C10 C6 18.9(6) . . . . ? C5 C6 C10 C9 0.6(7) . . . . ? C1 C6 C10 C9 -179.2(5) . . . . ? C5 C6 C10 N2 -177.7(4) . . . . ? C1 C6 C10 N2 2.5(7) . . . . ? C1 N1 C11 C13 161.9(4) . . . . ? Sb1 N1 C11 C13 -3.6(5) . . . . ? C1 N1 C11 C12 -75.1(5) . . . . ? Sb1 N1 C11 C12 119.4(4) . . . . ? C10 N2 C14 C16 -166.7(4) . . . . ? Sb1 N2 C14 C16 1.8(5) . . . . ? C10 N2 C14 C15 70.4(5) . . . . ? Sb1 N2 C14 C15 -121.1(4) . . . . ? O2 S1 C19 F3 -61.6(5) . . . . ? O3 S1 C19 F3 59.8(5) . . . . ? O1 S1 C19 F3 178.1(4) . . . . ? O2 S1 C19 F2 178.4(4) . . . . ? O3 S1 C19 F2 -60.3(5) . . . . ? O1 S1 C19 F2 58.1(5) . . . . ? O2 S1 C19 F1 59.0(5) . . . . ? O3 S1 C19 F1 -179.7(4) . . . . ? O1 S1 C19 F1 -61.3(5) . . . . ? N5 Sb2 N4 C20 26.5(4) . . . . ? N6 Sb2 N4 C20 -69.0(4) . . . . ? N5 Sb2 N4 C30 -160.9(4) . . . . ? N6 Sb2 N4 C30 103.6(4) . . . . ? N4 Sb2 N5 C29 -12.1(4) . . . . ? N6 Sb2 N5 C29 80.1(4) . . . . ? N4 Sb2 N5 C33 173.1(3) . . . . ? N6 Sb2 N5 C33 -94.7(3) . . . . ? N4 Sb2 N6 C36 59.1(5) . . . . ? N5 Sb2 N6 C36 -33.8(5) . . . . ? N4 Sb2 N6 C37 -68.1(4) . . . . ? N5 Sb2 N6 C37 -161.1(4) . . . . ? C30 N4 C20 C21 -18.5(7) . . . . ? Sb2 N4 C20 C21 154.1(4) . . . . ? C30 N4 C20 C25 159.6(4) . . . . ? Sb2 N4 C20 C25 -27.8(6) . . . . ? N4 C20 C21 C22 173.5(5) . . . . ? C25 C20 C21 C22 -4.7(7) . . . . ? C20 C21 C22 C23 0.6(8) . . . . ? C21 C22 C23 C24 1.2(8) . . . . ? C22 C23 C24 C26 -177.2(5) . . . . ? C22 C23 C24 C25 1.0(8) . . . . ? C21 C20 C25 C29 -174.8(5) . . . . ? N4 C20 C25 C29 7.1(7) . . . . ? C21 C20 C25 C24 6.6(7) . . . . ? N4 C20 C25 C24 -171.5(4) . . . . ? C26 C24 C25 C29 -5.5(7) . . . . ? C23 C24 C25 C29 176.4(4) . . . . ? C26 C24 C25 C20 173.3(5) . . . . ? C23 C24 C25 C20 -4.8(7) . . . . ? C23 C24 C26 C27 179.5(5) . . . . ? C25 C24 C26 C27 1.4(8) . . . . ? C24 C26 C27 C28 2.1(9) . . . . ? C26 C27 C28 C29 -1.3(9) . . . . ? C27 C28 C29 N5 175.8(5) . . . . ? C27 C28 C29 C25 -3.1(8) . . . . ? C33 N5 C29 C28 -6.3(7) . . . . ? Sb2 N5 C29 C28 179.1(4) . . . . ? C33 N5 C29 C25 172.5(4) . . . . ? Sb2 N5 C29 C25 -2.1(6) . . . . ? C20 C25 C29 C28 -172.5(5) . . . . ? C24 C25 C29 C28 6.2(7) . . . . ? C20 C25 C29 N5 8.7(7) . . . . ? C24 C25 C29 N5 -172.6(4) . . . . ? C20 N4 C30 C31 -66.2(6) . . . . ? Sb2 N4 C30 C31 120.8(5) . . . . ? C20 N4 C30 C32 170.5(5) . . . . ? Sb2 N4 C30 C32 -2.5(6) . . . . ? C29 N5 C33 C35 159.1(5) . . . . ? Sb2 N5 C33 C35 -25.7(5) . . . . ? C29 N5 C33 C34 -75.9(6) . . . . ? Sb2 N5 C33 C34 99.3(4) . . . . ? O6 S4 C38 F4 -79.9(6) . . . . ? O4 S4 C38 F4 38.2(6) . . . . ? O5 S4 C38 F4 156.5(5) . . . . ? O6 S4 C38 F5 159.0(6) . . . . ? O4 S4 C38 F5 -82.9(5) . . . . ? O5 S4 C38 F5 35.4(6) . . . . ? O6 S4 C38 F6 40.7(6) . . . . ? O4 S4 C38 F6 158.8(5) . . . . ? O5 S4 C38 F6 -83.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 24.80 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.850 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.096