# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Mohr, Fabian' _publ_contact_author_email fmohr@uni-wuppertal.de loop_ _publ_author_name A.Molter F.Mohr data_FMINS2 _database_code_depnum_ccdc_archive 'CCDC 800140' #TrackingRef 'Cifs-all.cif' _audit_creation_method SHELXL-97 _chemical_formula_moiety ? _chemical_formula_sum 'C10 H13 Br2 In N4 Se' _chemical_formula_weight 542.84 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? 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' In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 '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' _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_angle_alpha 67.763(5) _cell_angle_beta 84.663(4) _cell_angle_gamma 77.020(5) _cell_formula_units_Z 2 _cell_length_a 8.8744(5) _cell_length_b 9.0004(5) _cell_length_c 10.5203(6) _cell_measurement_reflns_used 3054 _cell_measurement_temperature 150.0 _cell_measurement_theta_min 2.5954 _cell_measurement_theta_max 29.0169 _cell_volume 757.90(7) _exptl_absorpt_coefficient_mu 9.221 _exptl_absorpt_correction_T_min 0.46956 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_F_000 508 _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 2.379 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_special_details ? _diffrn_ambient_temperature 150.0 _diffrn_detector_area_resol_mean 16.2705 _diffrn_measured_fraction_theta_full 0.949 _diffrn_measured_fraction_theta_max 0.814 _diffrn_measurement_device_type 'Oxford Diffraction Gemini Ultra' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0651 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5252 _diffrn_reflns_theta_full 25.05 _diffrn_reflns_theta_max 29.09 _diffrn_reflns_theta_min 3.06 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2454 _reflns_number_total 3313 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)/Bruker' _refine_diff_density_max 2.649 _refine_diff_density_min -2.079 _refine_diff_density_rms 0.459 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0410 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 3313 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1135 _refine_ls_wR_factor_ref 0.1483 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0950P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap 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 In1 In 0.35606(6) 0.11618(6) 0.29865(6) 0.01759(18) Uani 1 1 d . . . Se1 Se 0.10187(9) 0.16235(10) 0.42960(9) 0.0227(2) Uani 1 1 d . . . Br1 Br 0.28210(10) 0.10335(10) 0.07497(9) 0.0259(2) Uani 1 1 d . . . Br2 Br 0.48906(9) -0.17834(9) 0.43855(9) 0.0216(2) Uani 1 1 d . . . N1 N 0.5807(7) 0.1989(8) 0.2193(7) 0.0180(14) Uani 1 1 d . . . N4 N -0.0696(8) 0.4820(9) 0.3496(8) 0.0291(18) Uani 1 1 d . . . N2 N 0.3151(8) 0.3897(8) 0.2453(7) 0.0216(16) Uani 1 1 d . . . N3 N 0.1749(8) 0.4804(8) 0.2650(8) 0.0232(16) Uani 1 1 d . . . C7 C 0.4103(10) 0.6451(9) 0.1644(9) 0.026(2) Uani 1 1 d . . . H7AB H 0.4348 0.7002 0.0673 0.039 Uiso 1 1 calc R . . H7AC H 0.4818 0.6606 0.2216 0.039 Uiso 1 1 calc R . . H7AA H 0.3040 0.6919 0.1838 0.039 Uiso 1 1 calc R . . C1 C 0.5741(9) 0.3619(9) 0.1755(8) 0.0175(17) Uani 1 1 d . . . C6 C 0.4261(9) 0.4651(9) 0.1956(8) 0.0180(17) Uani 1 1 d . . . C2 C 0.7058(10) 0.4254(11) 0.1207(9) 0.0242(19) Uani 1 1 d . . . H2AA H 0.7026 0.5395 0.0923 0.029 Uiso 1 1 calc R . . C3 C 0.8423(10) 0.3183(11) 0.1083(10) 0.030(2) Uani 1 1 d . . . H3AA H 0.9324 0.3599 0.0698 0.036 Uiso 1 1 calc R . . C5 C 0.7123(10) 0.0988(10) 0.2054(10) 0.029(2) Uani 1 1 d . . . H5AA H 0.7142 -0.0151 0.2336 0.034 Uiso 1 1 calc R . . C10 C -0.1922(10) 0.4123(12) 0.4371(10) 0.031(2) Uani 1 1 d . . . H10A H -0.1688 0.2932 0.4617 0.046 Uiso 1 1 calc R . . H10B H -0.2905 0.4596 0.3880 0.046 Uiso 1 1 calc R . . H10C H -0.1999 0.4373 0.5207 0.046 Uiso 1 1 calc R . . C8 C 0.0700(9) 0.3943(10) 0.3355(9) 0.0225(18) Uani 1 1 d . . . C4 C 0.8465(10) 0.1561(12) 0.1509(10) 0.030(2) Uani 1 1 d . . . H4AA H 0.9391 0.0823 0.1439 0.036 Uiso 1 1 calc R . . C9 C -0.1032(11) 0.6627(11) 0.2814(11) 0.037(2) Uani 1 1 d . . . H9AC H -0.0306 0.7081 0.3137 0.056 Uiso 1 1 calc R . . H9AB H -0.2092 0.7071 0.3036 0.056 Uiso 1 1 calc R . . H9AA H -0.0919 0.6927 0.1818 0.056 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 In1 0.0156(3) 0.0126(3) 0.0208(3) -0.0021(2) 0.0004(2) -0.0026(2) Se1 0.0196(4) 0.0188(4) 0.0252(5) -0.0038(3) 0.0043(4) -0.0047(3) Br1 0.0277(5) 0.0263(4) 0.0235(4) -0.0078(4) -0.0018(4) -0.0071(3) Br2 0.0229(4) 0.0153(4) 0.0221(4) -0.0027(3) -0.0030(3) -0.0013(3) N1 0.020(3) 0.021(3) 0.011(3) -0.004(3) -0.006(3) -0.003(3) N4 0.022(4) 0.025(4) 0.034(4) -0.006(3) 0.003(3) -0.002(3) N2 0.020(3) 0.016(3) 0.022(4) -0.002(3) 0.002(3) -0.001(3) N3 0.022(4) 0.016(3) 0.028(4) -0.006(3) 0.002(3) 0.000(3) C7 0.037(5) 0.017(4) 0.028(5) -0.008(3) -0.005(4) -0.009(4) C1 0.019(4) 0.020(4) 0.013(4) -0.004(3) -0.005(3) -0.006(3) C6 0.025(4) 0.018(4) 0.013(4) -0.006(3) -0.004(3) -0.005(3) C2 0.031(5) 0.031(4) 0.016(4) -0.008(3) -0.006(4) -0.015(4) C3 0.024(4) 0.038(5) 0.028(5) -0.008(4) 0.002(4) -0.011(4) C5 0.023(4) 0.018(4) 0.036(5) -0.002(4) 0.003(4) 0.001(3) C10 0.018(4) 0.042(5) 0.035(5) -0.017(4) -0.001(4) -0.006(4) C8 0.021(4) 0.024(4) 0.023(4) -0.009(3) -0.004(4) -0.002(3) C4 0.021(4) 0.038(5) 0.029(5) -0.012(4) 0.005(4) -0.005(4) C9 0.033(5) 0.028(5) 0.043(6) -0.009(4) -0.001(5) 0.002(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 In1 N2 2.257(6) . ? In1 N1 2.261(6) . ? In1 Br1 2.5512(12) . ? In1 Br2 2.5594(9) . ? In1 Se1 2.5677(9) . ? Se1 C8 1.908(8) . ? N1 C5 1.339(10) . ? N1 C1 1.350(10) . ? N4 C8 1.339(10) . ? N4 C10 1.452(10) . ? N4 C9 1.479(11) . ? N2 C6 1.281(10) . ? N2 N3 1.372(9) . ? N3 C8 1.334(10) . ? C7 C6 1.502(10) . ? C7 H7AB 0.9800 . ? C7 H7AC 0.9800 . ? C7 H7AA 0.9800 . ? C1 C2 1.397(11) . ? C1 C6 1.477(10) . ? C2 C3 1.398(13) . ? C2 H2AA 0.9500 . ? C3 C4 1.348(13) . ? C3 H3AA 0.9500 . ? C5 C4 1.392(12) . ? C5 H5AA 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C4 H4AA 0.9500 . ? C9 H9AC 0.9800 . ? C9 H9AB 0.9800 . ? C9 H9AA 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 In1 N1 71.7(2) . . ? N2 In1 Br1 101.3(2) . . ? N1 In1 Br1 95.99(18) . . ? N2 In1 Br2 151.7(2) . . ? N1 In1 Br2 94.02(16) . . ? Br1 In1 Br2 104.40(4) . . ? N2 In1 Se1 79.52(16) . . ? N1 In1 Se1 146.51(18) . . ? Br1 In1 Se1 106.24(4) . . ? Br2 In1 Se1 104.01(3) . . ? C8 Se1 In1 91.9(2) . . ? C5 N1 C1 119.8(7) . . ? C5 N1 In1 124.1(6) . . ? C1 N1 In1 115.9(5) . . ? C8 N4 C10 124.1(7) . . ? C8 N4 C9 120.2(7) . . ? C10 N4 C9 115.6(7) . . ? C6 N2 N3 117.7(6) . . ? C6 N2 In1 119.7(5) . . ? N3 N2 In1 122.6(5) . . ? C8 N3 N2 115.6(6) . . ? C6 C7 H7AB 109.5 . . ? C6 C7 H7AC 109.5 . . ? H7AB C7 H7AC 109.5 . . ? C6 C7 H7AA 109.5 . . ? H7AB C7 H7AA 109.5 . . ? H7AC C7 H7AA 109.5 . . ? N1 C1 C2 120.1(7) . . ? N1 C1 C6 117.1(7) . . ? C2 C1 C6 122.7(7) . . ? N2 C6 C1 115.5(7) . . ? N2 C6 C7 122.8(7) . . ? C1 C6 C7 121.7(7) . . ? C1 C2 C3 119.0(8) . . ? C1 C2 H2AA 120.5 . . ? C3 C2 H2AA 120.5 . . ? C4 C3 C2 120.1(8) . . ? C4 C3 H3AA 119.9 . . ? C2 C3 H3AA 119.9 . . ? N1 C5 C4 122.2(8) . . ? N1 C5 H5AA 118.9 . . ? C4 C5 H5AA 118.9 . . ? N4 C10 H10A 109.5 . . ? N4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C8 N4 115.9(7) . . ? N3 C8 Se1 127.1(6) . . ? N4 C8 Se1 116.8(6) . . ? C3 C4 C5 118.7(8) . . ? C3 C4 H4AA 120.7 . . ? C5 C4 H4AA 120.7 . . ? N4 C9 H9AC 109.5 . . ? N4 C9 H9AB 109.5 . . ? H9AC C9 H9AB 109.5 . . ? N4 C9 H9AA 109.5 . . ? H9AC C9 H9AA 109.5 . . ? H9AB C9 H9AA 109.5 . . ? data_FMINS _database_code_depnum_ccdc_archive 'CCDC 800141' _audit_creation_method SHELXL-97 _chemical_formula_moiety ? _chemical_formula_sum 'C11 H17 Br2 In N4 O S' _chemical_formula_weight 527.99 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? 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' In In -0.7276 1.3100 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_angle_alpha 81.442(5) _cell_angle_beta 74.886(5) _cell_angle_gamma 71.157(5) _cell_formula_units_Z 2 _cell_length_a 7.1840(4) _cell_length_b 10.0281(6) _cell_length_c 12.6768(7) _cell_measurement_reflns_used 3589 _cell_measurement_temperature 150.0 _cell_measurement_theta_min 3.0689 _cell_measurement_theta_max 29.2338 _cell_volume 832.33(8) _exptl_absorpt_coefficient_mu 6.346 _exptl_absorpt_correction_T_min 0.37266 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_F_000 508 _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 2.107 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_special_details ? _diffrn_ambient_temperature 150.0 _diffrn_detector_area_resol_mean 16.2705 _diffrn_measured_fraction_theta_full 0.968 _diffrn_measured_fraction_theta_max 0.811 _diffrn_measurement_device_type 'Oxford Diffraction Gemini Ultra' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0673 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5858 _diffrn_reflns_theta_full 25.05 _diffrn_reflns_theta_max 29.24 _diffrn_reflns_theta_min 3.08 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2869 _reflns_number_total 3676 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)/Bruker' _refine_diff_density_max 1.195 _refine_diff_density_min -1.060 _refine_diff_density_rms 0.243 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0423 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 189 _refine_ls_number_reflns 3676 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0901 _refine_ls_wR_factor_ref 0.0987 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0499P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 In1 In 0.47193(5) 0.17402(4) 0.24866(3) 0.01554(11) Uani 1 1 d . . . Br2 Br 0.14405(8) 0.26178(6) 0.16601(4) 0.02465(15) Uani 1 1 d . . . Br1 Br 0.51559(9) -0.08755(7) 0.25825(5) 0.03099(17) Uani 1 1 d . . . S1 S 0.3267(2) 0.24775(16) 0.43846(11) 0.0231(3) Uani 1 1 d . . . O1 O 0.7989(5) 0.1104(5) 0.2866(3) 0.0262(9) Uani 1 1 d . . . N1 N 0.6612(6) 0.2056(5) 0.0789(3) 0.0170(9) Uani 1 1 d . . . N2 N 0.5064(6) 0.3904(5) 0.2320(3) 0.0147(9) Uani 1 1 d . . . N3 N 0.4247(6) 0.4790(5) 0.3141(3) 0.0174(9) Uani 1 1 d . . . C10 C 0.3379(7) 0.4224(6) 0.4087(4) 0.0192(11) Uani 1 1 d . . . C7 C 0.6539(8) 0.5724(6) 0.1237(4) 0.0220(12) Uani 1 1 d . . . H7B H 0.7973 0.5572 0.1197 0.033 Uiso 1 1 calc R . . H7C H 0.5716 0.6302 0.1848 0.033 Uiso 1 1 calc R . . H7A H 0.6203 0.6211 0.0551 0.033 Uiso 1 1 calc R . . C1 C 0.6981(7) 0.3312(6) 0.0540(4) 0.0169(11) Uani 1 1 d . . . C6 C 0.6122(7) 0.4332(6) 0.1410(4) 0.0156(10) Uani 1 1 d . . . C3 C 0.8866(8) 0.2613(7) -0.1251(5) 0.0290(14) Uani 1 1 d . . . H3A H 0.9635 0.2808 -0.1956 0.035 Uiso 1 1 calc R . . C4 C 0.8481(9) 0.1351(7) -0.0988(5) 0.0318(15) Uani 1 1 d . . . H4A H 0.8989 0.0651 -0.1505 0.038 Uiso 1 1 calc R . . C2 C 0.8125(8) 0.3613(7) -0.0479(4) 0.0233(12) Uani 1 1 d . . . H2A H 0.8397 0.4496 -0.0646 0.028 Uiso 1 1 calc R . . C5 C 0.7342(8) 0.1095(7) 0.0038(4) 0.0241(12) Uani 1 1 d . . . H5A H 0.7070 0.0212 0.0216 0.029 Uiso 1 1 calc R . . N4 N 0.2534(7) 0.5092(5) 0.4914(3) 0.0229(10) Uani 1 1 d . . . C11 C 0.8659(9) 0.0179(6) 0.3759(5) 0.0266(13) Uani 1 1 d . . . H11C H 1.0113 0.0007 0.3664 0.040 Uiso 1 1 calc R . . H11A H 0.8382 -0.0719 0.3772 0.040 Uiso 1 1 calc R . . H11B H 0.7938 0.0618 0.4450 0.040 Uiso 1 1 calc R . . C9 C 0.1726(8) 0.4610(7) 0.6039(4) 0.0271(13) Uani 1 1 d . . . H9A H 0.0415 0.4474 0.6087 0.041 Uiso 1 1 calc R . . H9C H 0.1558 0.5320 0.6539 0.041 Uiso 1 1 calc R . . H9B H 0.2665 0.3715 0.6245 0.041 Uiso 1 1 calc R . . C8 C 0.2454(9) 0.6572(7) 0.4727(5) 0.0285(14) Uani 1 1 d . . . H8B H 0.3806 0.6657 0.4647 0.043 Uiso 1 1 calc R . . H8C H 0.1525 0.7088 0.5349 0.043 Uiso 1 1 calc R . . H8A H 0.1977 0.6970 0.4057 0.043 Uiso 1 1 calc R . . H1A H 0.877(8) 0.169(6) 0.259(4) 0.017(14) 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 In1 0.01581(18) 0.0142(2) 0.01633(19) 0.00155(14) -0.00398(13) -0.00506(14) Br2 0.0187(3) 0.0292(4) 0.0285(3) 0.0097(2) -0.0113(2) -0.0108(2) Br1 0.0388(3) 0.0153(3) 0.0422(4) 0.0016(3) -0.0152(3) -0.0094(3) S1 0.0266(7) 0.0223(8) 0.0175(7) 0.0014(6) -0.0005(5) -0.0083(6) O1 0.0186(19) 0.032(3) 0.028(2) 0.0150(18) -0.0116(16) -0.0103(18) N1 0.018(2) 0.020(3) 0.012(2) -0.0017(18) -0.0056(16) -0.0021(19) N2 0.016(2) 0.014(2) 0.015(2) -0.0006(17) -0.0052(16) -0.0051(17) N3 0.019(2) 0.016(3) 0.018(2) -0.0032(18) -0.0047(17) -0.0043(19) C10 0.015(2) 0.019(3) 0.022(3) 0.001(2) -0.006(2) -0.002(2) C7 0.024(3) 0.020(3) 0.024(3) 0.000(2) -0.005(2) -0.011(2) C1 0.012(2) 0.022(3) 0.017(3) 0.003(2) -0.0065(19) -0.005(2) C6 0.015(2) 0.014(3) 0.020(3) 0.003(2) -0.0078(19) -0.005(2) C3 0.026(3) 0.037(4) 0.018(3) -0.004(3) 0.003(2) -0.006(3) C4 0.030(3) 0.034(4) 0.022(3) -0.012(3) -0.002(2) 0.004(3) C2 0.020(3) 0.030(4) 0.018(3) 0.003(2) -0.002(2) -0.008(2) C5 0.026(3) 0.020(3) 0.025(3) -0.004(2) -0.009(2) -0.001(2) N4 0.024(2) 0.023(3) 0.019(2) -0.004(2) -0.0047(18) -0.003(2) C11 0.033(3) 0.021(3) 0.022(3) 0.006(2) -0.011(2) -0.003(3) C9 0.029(3) 0.032(4) 0.017(3) -0.011(3) -0.002(2) -0.003(3) C8 0.028(3) 0.026(4) 0.033(3) -0.015(3) -0.004(2) -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 In1 N2 2.235(4) . ? In1 N1 2.265(4) . ? In1 O1 2.384(4) . ? In1 S1 2.4792(14) . ? In1 Br1 2.5273(7) . ? In1 Br2 2.6634(6) . ? S1 C10 1.759(6) . ? O1 C11 1.434(6) . ? O1 H1A 0.91(5) . ? N1 C5 1.340(7) . ? N1 C1 1.345(7) . ? N2 C6 1.304(6) . ? N2 N3 1.355(6) . ? N3 C10 1.336(7) . ? C10 N4 1.351(7) . ? C7 C6 1.494(7) . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7 H7A 0.9800 . ? C1 C2 1.388(7) . ? C1 C6 1.489(8) . ? C3 C4 1.357(9) . ? C3 C2 1.387(9) . ? C3 H3A 0.9500 . ? C4 C5 1.381(8) . ? C4 H4A 0.9500 . ? C2 H2A 0.9500 . ? C5 H5A 0.9500 . ? N4 C8 1.452(8) . ? N4 C9 1.466(7) . ? C11 H11C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C9 H9A 0.9800 . ? C9 H9C 0.9800 . ? C9 H9B 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C8 H8A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 In1 N1 72.32(15) . . ? N2 In1 O1 81.70(15) . . ? N1 In1 O1 79.36(14) . . ? N2 In1 S1 78.21(11) . . ? N1 In1 S1 149.32(12) . . ? O1 In1 S1 88.28(10) . . ? N2 In1 Br1 167.57(10) . . ? N1 In1 Br1 100.81(12) . . ? O1 In1 Br1 86.88(11) . . ? S1 In1 Br1 106.48(4) . . ? N2 In1 Br2 93.25(10) . . ? N1 In1 Br2 89.09(10) . . ? O1 In1 Br2 168.33(9) . . ? S1 In1 Br2 101.04(4) . . ? Br1 In1 Br2 97.04(2) . . ? C10 S1 In1 96.19(18) . . ? C11 O1 In1 126.7(3) . . ? C11 O1 H1A 112(4) . . ? In1 O1 H1A 118(4) . . ? C5 N1 C1 119.4(4) . . ? C5 N1 In1 124.5(4) . . ? C1 N1 In1 116.1(3) . . ? C6 N2 N3 118.1(4) . . ? C6 N2 In1 119.4(3) . . ? N3 N2 In1 122.6(3) . . ? C10 N3 N2 114.7(4) . . ? N3 C10 N4 115.8(5) . . ? N3 C10 S1 127.6(4) . . ? N4 C10 S1 116.6(4) . . ? C6 C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C7 H7A 109.5 . . ? H7B C7 H7A 109.5 . . ? H7C C7 H7A 109.5 . . ? N1 C1 C2 120.7(5) . . ? N1 C1 C6 116.7(4) . . ? C2 C1 C6 122.6(5) . . ? N2 C6 C1 115.5(5) . . ? N2 C6 C7 123.6(5) . . ? C1 C6 C7 120.8(4) . . ? C4 C3 C2 119.2(5) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 119.4(5) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C3 C2 C1 119.4(6) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? N1 C5 C4 121.9(6) . . ? N1 C5 H5A 119.1 . . ? C4 C5 H5A 119.1 . . ? C10 N4 C8 120.4(4) . . ? C10 N4 C9 123.2(5) . . ? C8 N4 C9 116.4(4) . . ? O1 C11 H11C 109.5 . . ? O1 C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11C C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C9 H9A 109.5 . . ? N4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? N4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? H9C C9 H9B 109.5 . . ? N4 C8 H8B 109.5 . . ? N4 C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N4 C8 H8A 109.5 . . ? H8B C8 H8A 109.5 . . ? H8C C8 H8A 109.5 . . ? data_AMS215_2 _database_code_depnum_ccdc_archive 'CCDC 800142' _audit_creation_method SHELXL-97 _chemical_formula_moiety ? _chemical_formula_sum 'C10 H13 Cl2 N4 Sb Se' _chemical_formula_weight 460.85 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? 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' Se Se -0.0929 2.2259 '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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz '-x, -y, -z' 'x, y, z' '-x+1/2, y+1/2, -z+1/2' 'x-1/2, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 96.400(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.4928(3) _cell_length_b 15.1918(6) _cell_length_c 11.4316(4) _cell_measurement_reflns_used 3197 _cell_measurement_temperature 150 _cell_measurement_theta_max 29.476 _cell_measurement_theta_min 3.1561 _cell_volume 1465.72(10) _exptl_absorpt_coefficient_mu 4.718 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.70702 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_F_000 880 _exptl_crystal_colour ? _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 2.088 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_special_details ? _diffrn_ambient_temperature 150.0 _diffrn_detector_area_resol_mean 16.2705 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.839 _diffrn_measurement_details ; 1 omega -42.00 10.00 1.0000 27.0000 omega____ theta____ kappa____ phi______ frames - -19.6975 -77.0000 -90.0000 52 2 omega -89.00 -6.00 1.0000 27.0000 omega____ theta____ kappa____ phi______ frames - -19.6975 -77.0000 120.0000 83 3 omega -59.00 -33.00 1.0000 27.0000 omega____ theta____ kappa____ phi______ frames - -19.6975 94.0000 -161.0000 26 4 omega -96.00 -24.00 1.0000 27.0000 omega____ theta____ kappa____ phi______ frames - -19.6975 161.0000 -53.0000 72 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0453809575 _diffrn_orient_matrix_UB_12 -0.0347792888 _diffrn_orient_matrix_UB_13 0.0279951457 _diffrn_orient_matrix_UB_21 -0.0692178615 _diffrn_orient_matrix_UB_22 -0.0261772223 _diffrn_orient_matrix_UB_23 -0.0014553542 _diffrn_orient_matrix_UB_31 0.0139532653 _diffrn_orient_matrix_UB_32 -0.0168539916 _diffrn_orient_matrix_UB_33 -0.0557098486 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0522 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6752 _diffrn_reflns_theta_full 25.05 _diffrn_reflns_theta_max 29.54 _diffrn_reflns_theta_min 3.23 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2356 _reflns_number_total 3434 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)/Bruker' _refine_diff_density_max 3.481 _refine_diff_density_min -1.112 _refine_diff_density_rms 0.153 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0375 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 160 _refine_ls_number_reflns 3434 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0946 _refine_ls_wR_factor_ref 0.0999 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.42595(4) 0.59398(2) 0.83223(3) 0.01987(11) Uani 1 1 d . . . Se1 Se 0.43118(7) 0.76811(4) 0.83721(5) 0.03154(16) Uani 1 1 d . . . Cl2 Cl 0.19096(14) 0.59921(9) 0.67232(11) 0.0281(3) Uani 1 1 d . . . Cl1 Cl 0.71154(16) 0.58917(10) 0.93715(11) 0.0312(3) Uani 1 1 d . . . C1 C 0.5980(5) 0.4693(4) 0.6617(4) 0.0179(10) Uani 1 1 d . . . C8 C 0.5311(5) 0.7731(4) 0.6986(4) 0.0218(11) Uani 1 1 d . . . N2 N 0.5633(4) 0.6232(3) 0.6814(3) 0.0204(9) Uani 1 1 d . . . N3 N 0.5873(5) 0.7068(3) 0.6432(4) 0.0197(9) Uani 1 1 d . . . C6 C 0.6305(5) 0.5608(3) 0.6284(4) 0.0187(10) Uani 1 1 d . . . N1 N 0.5011(5) 0.4619(3) 0.7480(4) 0.0226(9) Uani 1 1 d . . . N4 N 0.5549(5) 0.8535(3) 0.6520(4) 0.0248(10) Uani 1 1 d . . . C7 C 0.7401(6) 0.5806(4) 0.5391(4) 0.0240(12) Uani 1 1 d . . . H7B H 0.6887 0.6212 0.4802 0.036 Uiso 1 1 calc R . . H7A H 0.7670 0.5259 0.5004 0.036 Uiso 1 1 calc R . . H7C H 0.8370 0.6076 0.5778 0.036 Uiso 1 1 calc R . . C4 C 0.5158(6) 0.3049(4) 0.7374(5) 0.0328(10) Uani 1 1 d . . . H4 H 0.4848 0.2487 0.7631 0.039 Uiso 1 1 calc R . . C3 C 0.6161(6) 0.3136(4) 0.6510(5) 0.0273(12) Uani 1 1 d . . . H3 H 0.6578 0.2625 0.6179 0.033 Uiso 1 1 calc R . . C2 C 0.6568(6) 0.3958(3) 0.6119(5) 0.0239(11) Uani 1 1 d . . . H2 H 0.7245 0.4013 0.5515 0.029 Uiso 1 1 calc R . . C9 C 0.4961(7) 0.9350(4) 0.6993(5) 0.0324(13) Uani 1 1 d . . . H9A H 0.3935 0.9501 0.6561 0.049 Uiso 1 1 calc R . . H9C H 0.5718 0.9826 0.6907 0.049 Uiso 1 1 calc R . . H9B H 0.4837 0.9269 0.7828 0.049 Uiso 1 1 calc R . . C10 C 0.6296(7) 0.8608(4) 0.5454(5) 0.0339(13) Uani 1 1 d . . . H10B H 0.7184 0.8193 0.5482 0.051 Uiso 1 1 calc R . . H10C H 0.6690 0.9209 0.5378 0.051 Uiso 1 1 calc R . . H10A H 0.5524 0.8470 0.4777 0.051 Uiso 1 1 calc R . . C5 C 0.4605(6) 0.3845(4) 0.7869(6) 0.0328(10) Uani 1 1 d . . . H5 H 0.3939 0.3813 0.8483 0.039 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 0.02147(18) 0.01877(19) 0.02070(17) -0.00144(16) 0.00828(12) 0.00097(15) Se1 0.0366(3) 0.0253(3) 0.0350(3) -0.0044(3) 0.0144(2) 0.0020(3) Cl2 0.0220(6) 0.0285(8) 0.0343(7) -0.0033(6) 0.0052(5) 0.0007(5) Cl1 0.0321(7) 0.0327(8) 0.0275(6) -0.0006(6) -0.0029(5) 0.0042(6) C1 0.012(2) 0.023(3) 0.017(2) -0.002(2) -0.0019(18) 0.003(2) C8 0.013(2) 0.029(3) 0.024(2) -0.004(2) 0.0012(19) 0.001(2) N2 0.017(2) 0.023(2) 0.021(2) 0.0037(18) 0.0038(17) -0.0030(18) N3 0.022(2) 0.015(2) 0.023(2) 0.0009(18) 0.0068(17) -0.0010(17) C6 0.017(2) 0.017(3) 0.021(2) -0.001(2) -0.0010(19) 0.001(2) N1 0.023(2) 0.019(2) 0.026(2) -0.0038(19) 0.0013(18) 0.0013(19) N4 0.026(2) 0.019(2) 0.029(2) -0.002(2) 0.0007(19) 0.0021(19) C7 0.021(3) 0.027(3) 0.025(2) 0.001(2) 0.007(2) 0.004(2) C4 0.0205(19) 0.027(2) 0.048(3) 0.019(2) -0.0087(17) -0.0086(16) C3 0.023(3) 0.016(3) 0.040(3) 0.003(3) -0.007(2) 0.003(2) C2 0.023(3) 0.021(3) 0.027(3) -0.005(2) 0.001(2) 0.004(2) C9 0.036(3) 0.026(3) 0.034(3) -0.002(3) -0.002(2) 0.004(3) C10 0.038(3) 0.022(3) 0.043(3) 0.000(3) 0.009(3) -0.003(3) C5 0.0205(19) 0.027(2) 0.048(3) 0.019(2) -0.0087(17) -0.0086(16) _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 Se1 2.6462(7) . ? Sb1 Cl2 2.5529(13) . ? Sb1 Cl1 2.5843(13) . ? Sb1 N2 2.231(4) . ? Sb1 N1 2.345(4) . ? Se1 C8 1.881(5) . ? C1 C6 1.476(7) . ? C1 N1 1.357(6) . ? C1 C2 1.372(7) . ? C8 N3 1.308(7) . ? C8 N4 1.358(7) . ? N2 N3 1.365(6) . ? N2 C6 1.292(6) . ? C6 C7 1.487(6) . ? N1 C5 1.317(7) . ? N4 C9 1.461(7) . ? N4 C10 1.439(7) . ? C7 H7B 0.9800 . ? C7 H7A 0.9800 . ? C7 H7C 0.9800 . ? C4 H4 0.9500 . ? C4 C3 1.381(8) . ? C4 C5 1.436(8) . ? C3 H3 0.9500 . ? C3 C2 1.382(7) . ? C2 H2 0.9500 . ? C9 H9A 0.9800 . ? C9 H9C 0.9800 . ? C9 H9B 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10 H10A 0.9800 . ? C5 H5 0.9500 . ? 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 Cl2 Sb1 Se1 89.67(4) . . ? Cl2 Sb1 Cl1 162.10(4) . . ? Cl1 Sb1 Se1 90.32(4) . . ? C1 C6 C7 121.1(4) . . ? C1 N1 Sb1 116.3(3) . . ? C1 C2 C3 119.0(5) . . ? C1 C2 H2 120.5 . . ? C8 Se1 Sb1 91.71(17) . . ? C8 N3 N2 119.1(4) . . ? C8 N4 C9 123.1(4) . . ? C8 N4 C10 120.0(5) . . ? N2 Sb1 Se1 78.99(12) . . ? N2 Sb1 Cl2 82.80(10) . . ? N2 Sb1 Cl1 79.63(10) . . ? N2 Sb1 N1 70.31(15) . . ? N2 C6 C1 117.7(4) . . ? N2 C6 C7 121.1(5) . . ? N3 C8 Se1 126.9(4) . . ? N3 C8 N4 115.2(5) . . ? N3 N2 Sb1 122.8(3) . . ? C6 N2 Sb1 120.9(4) . . ? C6 N2 N3 116.3(4) . . ? C6 C7 H7B 109.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7C 109.5 . . ? N1 Sb1 Se1 149.28(11) . . ? N1 Sb1 Cl2 87.68(10) . . ? N1 Sb1 Cl1 83.22(10) . . ? N1 C1 C6 114.3(4) . . ? N1 C1 C2 120.9(5) . . ? N1 C5 C4 120.6(6) . . ? N1 C5 H5 119.7 . . ? N4 C8 Se1 117.9(4) . . ? N4 C9 H9A 109.5 . . ? N4 C9 H9C 109.5 . . ? N4 C9 H9B 109.5 . . ? N4 C10 H10B 109.5 . . ? N4 C10 H10C 109.5 . . ? N4 C10 H10A 109.5 . . ? H7B C7 H7A 109.5 . . ? H7B C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? C4 C3 H3 119.5 . . ? C4 C3 C2 120.9(5) . . ? C4 C5 H5 119.7 . . ? C3 C4 H4 121.4 . . ? C3 C4 C5 117.1(5) . . ? C3 C2 H2 120.5 . . ? C2 C1 C6 124.9(5) . . ? C2 C3 H3 119.5 . . ? H9A C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9C C9 H9B 109.5 . . ? C10 N4 C9 116.7(5) . . ? H10B C10 H10C 109.5 . . ? H10B C10 H10A 109.5 . . ? H10C C10 H10A 109.5 . . ? C5 N1 Sb1 122.1(4) . . ? C5 N1 C1 121.5(5) . . ? C5 C4 H4 121.4 . . ? data_FMSBS_2 _database_code_depnum_ccdc_archive 'CCDC 803630' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C10 H13 Cl2 N4 S Sb' _chemical_formula_sum 'C10 H13 Cl2 N4 S Sb' _chemical_formula_weight 413.95 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? 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' Cl Cl 0.1484 0.1585 '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' 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 Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 95.786(13) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.3795(12) _cell_length_b 15.2295(17) _cell_length_c 11.4394(18) _cell_measurement_reflns_used 1121 _cell_measurement_temperature 150 _cell_measurement_theta_max 29.1548 _cell_measurement_theta_min 3.1687 _cell_volume 1452.4(3) _exptl_absorpt_coefficient_mu 2.399 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.35297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_F_000 808 _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.893 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_special_details ? _diffrn_ambient_temperature 150 _diffrn_detector_area_resol_mean 16.2705 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.845 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 1.00 41.00 1.0000 110.0000 omega____ theta____ kappa____ phi______ frames - 18.0026 77.0000 -90.0000 40 #__ type_ start__ end____ width___ exp.time_ 2 omega -90.00 -1.00 1.0000 110.0000 omega____ theta____ kappa____ phi______ frames - -19.7214 -37.0000 -60.0000 89 #__ type_ start__ end____ width___ exp.time_ 3 omega -91.00 4.00 1.0000 110.0000 omega____ theta____ kappa____ phi______ frames - -19.7214 -37.0000 -150.0000 95 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0654402789 _diffrn_orient_matrix_UB_12 -0.0058482571 _diffrn_orient_matrix_UB_13 0.0339982446 _diffrn_orient_matrix_UB_21 -0.0542154392 _diffrn_orient_matrix_UB_22 0.0078841129 _diffrn_orient_matrix_UB_23 -0.0505660666 _diffrn_orient_matrix_UB_31 -0.0009852063 _diffrn_orient_matrix_UB_32 -0.0455050421 _diffrn_orient_matrix_UB_33 -0.0131813186 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.1813 _diffrn_reflns_av_sigmaI/netI 0.3835 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 5999 _diffrn_reflns_theta_full 25.05 _diffrn_reflns_theta_max 29.23 _diffrn_reflns_theta_min 3.18 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1157 _reflns_number_total 3342 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution ; A short history of SHELX (Sheldrick, 2007)/Bruker ; _refine_diff_density_max 1.697 _refine_diff_density_min -0.847 _refine_diff_density_rms 0.200 _refine_ls_R_factor_all 0.2101 _refine_ls_R_factor_gt 0.0622 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.730 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 126 _refine_ls_number_reflns 3342 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.730 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.0841 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0147P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.42788(10) 0.09652(4) 0.83056(6) 0.01884(19) Uani 1 1 d . . . S1 S 0.4346(4) 0.26295(14) 0.8264(3) 0.0318(7) Uani 1 1 d . . . Cl2 Cl 0.1902(2) 0.10069(18) 0.67388(19) 0.0273(6) Uani 1 1 d . . . Cl1 Cl 0.7156(3) 0.09181(18) 0.93402(18) 0.0298(6) Uani 1 1 d . . . N2 N 0.5663(10) 0.1237(4) 0.6788(7) 0.0232(19) Uani 1 1 d . . . N3 N 0.5929(9) 0.2077(4) 0.6411(6) 0.016(2) Uiso 1 1 d . . . N1 N 0.5020(10) -0.0368(5) 0.7472(7) 0.025(2) Uani 1 1 d . . . C3 C 0.6118(11) -0.1847(6) 0.6500(8) 0.015(3) Uiso 1 1 d . . . H3 H 0.6521 -0.2365 0.6173 0.018 Uiso 1 1 calc R . . C4 C 0.6552(10) -0.1048(6) 0.6094(7) 0.025(2) Uiso 1 1 d . . . H4 H 0.7217 -0.1010 0.5471 0.029 Uiso 1 1 calc R . . C5 C 0.6002(12) -0.0286(5) 0.6607(9) 0.014(3) Uiso 1 1 d . . . C1 C 0.4571(11) -0.1132(6) 0.7918(8) 0.027(3) Uiso 1 1 d . . . H1 H 0.3931 -0.1159 0.8557 0.033 Uiso 1 1 calc R . . C2 C 0.5125(13) -0.1917(7) 0.7362(9) 0.033(3) Uani 1 1 d . . . H2 H 0.4792 -0.2479 0.7601 0.040 Uiso 1 1 calc R . . C8 C 0.5312(11) 0.2717(6) 0.6999(8) 0.019(2) Uiso 1 1 d . . . C6 C 0.6340(11) 0.0613(5) 0.6269(8) 0.019(2) Uiso 1 1 d . . . N4 N 0.5540(11) 0.3540(4) 0.6574(7) 0.024(2) Uiso 1 1 d . . . C7 C 0.7462(11) 0.0839(7) 0.5345(7) 0.028(3) Uani 1 1 d . . . H7B H 0.7843 0.0296 0.5006 0.042 Uiso 1 1 calc R . . H7C H 0.8380 0.1173 0.5711 0.042 Uiso 1 1 calc R . . H7A H 0.6885 0.1193 0.4724 0.042 Uiso 1 1 calc R . . C10 C 0.6331(11) 0.3633(5) 0.5522(8) 0.027(3) Uani 1 1 d . . . H10B H 0.7064 0.3138 0.5457 0.041 Uiso 1 1 calc R . . H10C H 0.6939 0.4183 0.5556 0.041 Uiso 1 1 calc R . . H10A H 0.5528 0.3641 0.4837 0.041 Uiso 1 1 calc R . . C9 C 0.4910(12) 0.4319(5) 0.7070(9) 0.032(3) Uani 1 1 d . . . H9C H 0.5719 0.4786 0.7102 0.048 Uiso 1 1 calc R . . H9B H 0.4637 0.4193 0.7866 0.048 Uiso 1 1 calc R . . H9A H 0.3946 0.4510 0.6580 0.048 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 0.0245(4) 0.0149(3) 0.0185(3) -0.0013(5) 0.0094(3) -0.0004(5) S1 0.0378(17) 0.0204(13) 0.0390(17) -0.0042(16) 0.0127(13) 0.0037(17) Cl2 0.0228(14) 0.0269(14) 0.0330(15) -0.0071(15) 0.0066(11) -0.0041(15) Cl1 0.0360(16) 0.0276(14) 0.0250(14) 0.0021(15) -0.0016(11) 0.0050(16) N2 0.019(4) 0.026(5) 0.023(4) -0.013(4) -0.005(3) 0.008(5) N1 0.014(5) 0.041(5) 0.019(5) -0.001(5) -0.007(4) -0.009(4) C2 0.032(7) 0.036(7) 0.029(7) 0.004(6) -0.005(5) -0.023(6) C7 0.019(6) 0.043(7) 0.023(6) 0.000(6) 0.004(5) 0.003(6) C10 0.022(7) 0.018(5) 0.042(7) 0.006(5) 0.000(5) -0.003(5) C9 0.030(7) 0.012(6) 0.052(8) -0.006(5) 0.000(5) 0.000(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 S1 2.536(2) . ? Sb1 Cl2 2.542(2) . ? Sb1 Cl1 2.577(3) . ? Sb1 N2 2.222(8) . ? Sb1 N1 2.353(8) . ? S1 C8 1.733(9) . ? N2 N3 1.376(8) . ? N2 C6 1.282(9) . ? N3 C8 1.319(9) . ? N1 C5 1.355(11) . ? N1 C1 1.339(10) . ? C3 H3 0.9500 . ? C3 C4 1.364(12) . ? C3 C2 1.357(12) . ? C4 H4 0.9500 . ? C4 C5 1.400(12) . ? C5 C6 1.459(11) . ? C1 H1 0.9500 . ? C1 C2 1.452(12) . ? C2 H2 0.9500 . ? C8 N4 1.365(10) . ? C6 C7 1.523(10) . ? N4 C10 1.438(11) . ? N4 C9 1.438(9) . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7 H7A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10 H10A 0.9800 . ? C9 H9C 0.9800 . ? C9 H9B 0.9800 . ? C9 H9A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 Sb1 Cl2 88.80(11) . . ? S1 Sb1 Cl1 90.86(11) . . ? Cl2 Sb1 Cl1 162.64(6) . . ? N2 Sb1 S1 77.58(17) . . ? N2 Sb1 Cl2 83.0(2) . . ? N2 Sb1 Cl1 80.0(2) . . ? N2 Sb1 N1 70.4(2) . . ? N2 C6 C5 117.7(8) . . ? N2 C6 C7 119.2(8) . . ? N3 N2 Sb1 122.2(5) . . ? N3 C8 S1 127.6(7) . . ? N3 C8 N4 114.8(8) . . ? N1 Sb1 S1 148.0(2) . . ? N1 Sb1 Cl2 87.5(2) . . ? N1 Sb1 Cl1 83.6(2) . . ? N1 C5 C4 118.7(8) . . ? N1 C5 C6 115.4(8) . . ? N1 C1 H1 122.2 . . ? N1 C1 C2 115.7(8) . . ? C3 C4 H4 120.4 . . ? C3 C4 C5 119.1(8) . . ? C3 C2 C1 120.0(9) . . ? C3 C2 H2 120.0 . . ? C4 C3 H3 119.3 . . ? C4 C5 C6 125.9(8) . . ? C5 N1 Sb1 114.9(6) . . ? C5 C4 H4 120.4 . . ? C5 C6 C7 123.1(8) . . ? C1 N1 Sb1 120.0(6) . . ? C1 N1 C5 124.9(8) . . ? C1 C2 H2 120.0 . . ? C2 C3 H3 119.3 . . ? C2 C3 C4 121.4(10) . . ? C2 C1 H1 122.2 . . ? C8 S1 Sb1 96.1(3) . . ? C8 N3 N2 116.2(7) . . ? C8 N4 C10 118.8(7) . . ? C8 N4 C9 123.2(8) . . ? C6 N2 Sb1 120.9(5) . . ? C6 N2 N3 116.7(8) . . ? C6 C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? C6 C7 H7A 109.5 . . ? N4 C8 S1 117.5(7) . . ? N4 C10 H10B 109.5 . . ? N4 C10 H10C 109.5 . . ? N4 C10 H10A 109.5 . . ? N4 C9 H9C 109.5 . . ? N4 C9 H9B 109.5 . . ? N4 C9 H9A 109.5 . . ? H7B C7 H7C 109.5 . . ? H7B C7 H7A 109.5 . . ? H7C C7 H7A 109.5 . . ? C10 N4 C9 117.8(7) . . ? H10B C10 H10C 109.5 . . ? H10B C10 H10A 109.5 . . ? H10C C10 H10A 109.5 . . ? H9C C9 H9B 109.5 . . ? H9C C9 H9A 109.5 . . ? H9B C9 H9A 109.5 . . ?