# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_msicl _database_code_depnum_ccdc_archive 'CCDC 889628' #TrackingRef 'web_deposit_cif_file_0_AlexanderKorlyukov_1341240229.all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H19 N2 O2 S2 Si, Cl' _chemical_formula_sum 'C9 H19 Cl N2 O2 S2 Si' _chemical_formula_weight 314.92 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' Si Si 0.0817 0.0704 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P n' _symmetry_space_group_name_Hall 'P -2yac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 7.9299(4) _cell_length_b 9.3820(5) _cell_length_c 9.9990(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.4890(10) _cell_angle_gamma 90.00 _cell_volume 743.66(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9959 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 31.08 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.611 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8876 _exptl_absorpt_correction_T_max 0.9193 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1998a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Smart 1000 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13827 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 29.99 _reflns_number_total 4269 _reflns_number_gt 4163 _reflns_threshold_expression I>2u(I) _computing_data_collection 'SMART (Bruker, 1998b)' _computing_cell_refinement 'SAINTPlus (Bruker, 1998a)' _computing_data_reduction 'SAINTPlus (Bruker, 1998a)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _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^)+(0.0202P)^2^+0.6370P] 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(5) _refine_ls_number_reflns 4269 _refine_ls_number_parameters 159 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0649 _refine_ls_wR_factor_gt 0.0643 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.12784(6) 0.00231(5) 0.10075(5) 0.02295(9) Uani 1 1 d . . . S1 S 0.47437(5) 0.38771(4) 0.34779(4) 0.01878(8) Uani 1 1 d . . . S2 S 0.21450(5) 0.71377(5) 0.43298(5) 0.02196(9) Uani 1 1 d . . . Si1 Si 0.40077(6) 0.55469(5) 0.48365(5) 0.01615(9) Uani 1 1 d . . . O1 O 0.21920(16) 0.44326(13) 0.53213(12) 0.0183(2) Uani 1 1 d . . . O2 O 0.56271(15) 0.66382(13) 0.40443(13) 0.0169(2) Uani 1 1 d . . . N1 N 0.03490(19) 0.26951(16) 0.48201(14) 0.0181(3) Uani 1 1 d . . . N2 N 0.64516(19) 0.85589(16) 0.29067(15) 0.0181(3) Uani 1 1 d . . . C1 C 0.1856(2) 0.32469(18) 0.47246(17) 0.0164(3) Uani 1 1 d . . . C2 C 0.3232(2) 0.25305(19) 0.39682(18) 0.0181(3) Uani 1 1 d . . . H2A H 0.2749 0.2049 0.3165 0.022 Uiso 1 1 calc R . . H2B H 0.3799 0.1804 0.4540 0.022 Uiso 1 1 calc R . . C3 C -0.1016(2) 0.3474(2) 0.54648(19) 0.0237(4) Uani 1 1 d . . . H3A H -0.0537 0.4105 0.6157 0.036 Uiso 1 1 calc R . . H3B H -0.1787 0.2794 0.5873 0.036 Uiso 1 1 calc R . . H3C H -0.1636 0.4044 0.4794 0.036 Uiso 1 1 calc R . . C4 C -0.0097(3) 0.1328(2) 0.4175(2) 0.0269(4) Uani 1 1 d . . . H4A H 0.0881 0.0688 0.4218 0.040 Uiso 1 1 calc R . . H4B H -0.0430 0.1496 0.3238 0.040 Uiso 1 1 calc R . . H4C H -0.1037 0.0890 0.4642 0.040 Uiso 1 1 calc R . . C5 C 0.5275(2) 0.78603(17) 0.35290(16) 0.0160(3) Uani 1 1 d . . . C6 C 0.3546(2) 0.84744(18) 0.36835(18) 0.0183(3) Uani 1 1 d . . . H6A H 0.3105 0.8817 0.2806 0.022 Uiso 1 1 calc R . . H6B H 0.3604 0.9297 0.4303 0.022 Uiso 1 1 calc R . . C7 C 0.8195(2) 0.8022(2) 0.3005(2) 0.0230(4) Uani 1 1 d . . . H7A H 0.8213 0.7013 0.2753 0.035 Uiso 1 1 calc R . . H7B H 0.8628 0.8128 0.3927 0.035 Uiso 1 1 calc R . . H7C H 0.8904 0.8567 0.2401 0.035 Uiso 1 1 calc R . . C8 C 0.6175(3) 1.0019(2) 0.2409(2) 0.0232(4) Uani 1 1 d . . . H8A H 0.5064 1.0080 0.1960 0.035 Uiso 1 1 calc R . . H8B H 0.7051 1.0262 0.1774 0.035 Uiso 1 1 calc R . . H8C H 0.6225 1.0688 0.3162 0.035 Uiso 1 1 calc R . . C9 C 0.4968(3) 0.5617(2) 0.65499(19) 0.0266(4) Uani 1 1 d . . . H9A H 0.4075 0.5695 0.7205 0.040 Uiso 1 1 calc R . . H9B H 0.5715 0.6447 0.6627 0.040 Uiso 1 1 calc R . . H9C H 0.5621 0.4746 0.6721 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.02216(19) 0.0287(2) 0.01803(16) 0.00397(15) 0.00204(14) 0.00669(16) S1 0.01796(18) 0.01499(17) 0.02359(19) -0.00121(15) 0.00427(14) -0.00070(14) S2 0.01421(18) 0.01699(19) 0.0347(2) 0.00050(17) 0.00050(16) 0.00067(15) Si1 0.0157(2) 0.0136(2) 0.0191(2) -0.00056(16) -0.00024(16) -0.00070(16) O1 0.0192(6) 0.0152(6) 0.0205(6) -0.0032(4) 0.0046(5) -0.0031(4) O2 0.0134(5) 0.0138(5) 0.0235(6) 0.0026(5) -0.0013(4) -0.0006(4) N1 0.0171(7) 0.0211(7) 0.0160(6) -0.0022(5) 0.0009(5) -0.0039(5) N2 0.0195(7) 0.0168(7) 0.0179(7) -0.0006(5) -0.0001(5) -0.0002(5) C1 0.0167(8) 0.0160(7) 0.0165(7) 0.0033(6) -0.0003(6) -0.0022(6) C2 0.0165(8) 0.0170(8) 0.0207(8) -0.0014(6) 0.0022(6) -0.0016(6) C3 0.0176(8) 0.0307(9) 0.0229(8) -0.0005(7) 0.0034(6) 0.0011(7) C4 0.0269(9) 0.0297(10) 0.0244(9) -0.0074(7) 0.0059(7) -0.0127(8) C5 0.0172(7) 0.0151(7) 0.0157(7) -0.0014(6) -0.0023(6) -0.0005(6) C6 0.0167(8) 0.0138(7) 0.0243(8) 0.0018(6) -0.0036(6) 0.0002(6) C7 0.0178(8) 0.0214(8) 0.0301(9) -0.0018(7) 0.0048(7) -0.0019(6) C8 0.0258(9) 0.0199(8) 0.0236(8) 0.0052(6) -0.0009(7) -0.0037(7) C9 0.0310(10) 0.0279(9) 0.0205(8) 0.0028(7) -0.0058(7) -0.0068(8) _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 S1 C2 1.8176(18) . ? S1 Si1 2.1637(6) . ? S2 C6 1.8062(18) . ? S2 Si1 2.1511(6) . ? Si1 O2 1.8379(13) . ? Si1 O1 1.8540(13) . ? Si1 C9 1.8580(19) . ? O1 C1 1.287(2) . ? O2 C5 1.285(2) . ? N1 C1 1.308(2) . ? N1 C3 1.469(2) . ? N1 C4 1.475(2) . ? N2 C5 1.311(2) . ? N2 C8 1.472(2) . ? N2 C7 1.472(2) . ? C1 C2 1.502(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.499(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? 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 C2 S1 Si1 98.24(6) . . ? C6 S2 Si1 98.10(6) . . ? O2 Si1 O1 169.39(6) . . ? O2 Si1 C9 95.93(8) . . ? O1 Si1 C9 94.67(8) . . ? O2 Si1 S2 89.72(4) . . ? O1 Si1 S2 85.39(5) . . ? C9 Si1 S2 117.07(8) . . ? O2 Si1 S1 85.98(4) . . ? O1 Si1 S1 88.85(4) . . ? C9 Si1 S1 119.59(8) . . ? S2 Si1 S1 123.32(3) . . ? C1 O1 Si1 121.26(11) . . ? C5 O2 Si1 121.53(11) . . ? C1 N1 C3 121.34(16) . . ? C1 N1 C4 121.42(16) . . ? C3 N1 C4 116.99(15) . . ? C5 N2 C8 121.61(15) . . ? C5 N2 C7 118.43(15) . . ? C8 N2 C7 118.20(15) . . ? O1 C1 N1 119.12(16) . . ? O1 C1 C2 118.42(15) . . ? N1 C1 C2 122.44(16) . . ? C1 C2 S1 108.51(12) . . ? C1 C2 H2A 110.0 . . ? S1 C2 H2A 110.0 . . ? C1 C2 H2B 110.0 . . ? S1 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 N2 119.11(15) . . ? O2 C5 C6 119.46(15) . . ? N2 C5 C6 121.41(15) . . ? C5 C6 S2 110.04(12) . . ? C5 C6 H6A 109.7 . . ? S2 C6 H6A 109.7 . . ? C5 C6 H6B 109.7 . . ? S2 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? Si1 C9 H9A 109.5 . . ? Si1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? Si1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 S2 Si1 O2 -6.53(7) . . . . ? C6 S2 Si1 O1 -177.11(7) . . . . ? C6 S2 Si1 C9 89.99(10) . . . . ? C6 S2 Si1 S1 -91.54(7) . . . . ? C2 S1 Si1 O2 -177.95(7) . . . . ? C2 S1 Si1 O1 -7.21(7) . . . . ? C2 S1 Si1 C9 87.51(10) . . . . ? C2 S1 Si1 S2 -90.93(7) . . . . ? O2 Si1 O1 C1 55.2(4) . . . . ? C9 Si1 O1 C1 -125.18(14) . . . . ? S2 Si1 O1 C1 117.98(13) . . . . ? S1 Si1 O1 C1 -5.58(13) . . . . ? O1 Si1 O2 C5 64.2(4) . . . . ? C9 Si1 O2 C5 -115.41(14) . . . . ? S2 Si1 O2 C5 1.79(12) . . . . ? S1 Si1 O2 C5 125.22(12) . . . . ? Si1 O1 C1 N1 -161.19(12) . . . . ? Si1 O1 C1 C2 20.2(2) . . . . ? C3 N1 C1 O1 6.9(3) . . . . ? C4 N1 C1 O1 -178.99(16) . . . . ? C3 N1 C1 C2 -174.59(16) . . . . ? C4 N1 C1 C2 -0.5(3) . . . . ? O1 C1 C2 S1 -24.8(2) . . . . ? N1 C1 C2 S1 156.62(14) . . . . ? Si1 S1 C2 C1 17.14(12) . . . . ? Si1 O2 C5 N2 -176.01(12) . . . . ? Si1 O2 C5 C6 5.7(2) . . . . ? C8 N2 C5 O2 -174.06(15) . . . . ? C7 N2 C5 O2 -9.4(2) . . . . ? C8 N2 C5 C6 4.2(2) . . . . ? C7 N2 C5 C6 168.85(16) . . . . ? O2 C5 C6 S2 -11.2(2) . . . . ? N2 C5 C6 S2 170.46(13) . . . . ? Si1 S2 C6 C5 10.27(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.344 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.059 data_1 _database_code_depnum_ccdc_archive 'CCDC 889629' #TrackingRef 'web_deposit_cif_file_0_AlexanderKorlyukov_1341240229.all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C9 H19 Ge N2 O2 S2), H2 O, 2(Br)' _chemical_formula_sum 'C18 H40 Br2 Ge2 N4 O5 S4' _chemical_formula_weight 825.78 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ge Ge 0.1547 1.8001 '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 Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.0970(13) _cell_length_b 8.0810(4) _cell_length_c 19.9782(11) _cell_angle_alpha 90.00 _cell_angle_beta 128.8890(10) _cell_angle_gamma 90.00 _cell_volume 3153.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5711 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 30.50 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.739 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 4.739 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5177 _exptl_absorpt_correction_T_max 0.6237 _exptl_absorpt_process_details 'APEX2 (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20463 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 31.00 _reflns_number_total 4959 _reflns_number_gt 4077 _reflns_threshold_expression I>2u(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'APEX2 (Bruker, 2005)' _computing_data_reduction 'APEX2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _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^)+(0.0319P)^2^+1.5592P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4959 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0643 _refine_ls_wR_factor_gt 0.0602 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.028564(11) 0.24386(3) 0.149583(13) 0.02256(6) Uani 1 1 d . . . Ge1 Ge 0.243705(10) 0.56968(2) 0.143034(13) 0.01344(5) Uani 1 1 d . . . S1 S 0.14295(3) 0.68467(6) 0.08253(3) 0.01919(11) Uani 1 1 d . . . S2 S 0.28113(3) 0.52254(6) 0.06982(3) 0.01826(10) Uani 1 1 d . . . O1 O 0.19214(7) 0.35178(17) 0.09182(9) 0.0178(3) Uani 1 1 d . . . O2 O 0.28119(7) 0.80059(17) 0.16256(9) 0.0161(3) Uani 1 1 d . . . N1 N 0.09120(9) 0.2226(2) -0.00097(11) 0.0162(3) Uani 1 1 d . . . N2 N 0.35117(9) 0.9759(2) 0.16427(11) 0.0156(3) Uani 1 1 d . . . C1 C 0.12714(10) 0.3517(2) 0.04587(12) 0.0147(4) Uani 1 1 d . . . C2 C 0.09071(10) 0.5004(2) 0.04497(14) 0.0185(4) Uani 1 1 d . . . H2A H 0.0779 0.4785 0.0820 0.022 Uiso 1 1 calc R . . H2B H 0.0481 0.5191 -0.0144 0.022 Uiso 1 1 calc R . . C3 C 0.12528(12) 0.0793(3) -0.00367(17) 0.0274(5) Uani 1 1 d . . . H3A H 0.1654 0.0501 0.0549 0.041 Uiso 1 1 calc R . . H3B H 0.1398 0.1062 -0.0379 0.041 Uiso 1 1 calc R . . H3C H 0.0935 -0.0144 -0.0299 0.041 Uiso 1 1 calc R . . C4 C 0.01616(11) 0.2149(3) -0.05220(15) 0.0249(5) Uani 1 1 d . . . H4A H 0.0041 0.2379 -0.0150 0.037 Uiso 1 1 calc R . . H4B H -0.0001 0.1043 -0.0773 0.037 Uiso 1 1 calc R . . H4C H -0.0053 0.2975 -0.0983 0.037 Uiso 1 1 calc R . . C5 C 0.32268(10) 0.8298(2) 0.14735(12) 0.0143(4) Uani 1 1 d . . . C6 C 0.33992(10) 0.6966(2) 0.11111(13) 0.0174(4) Uani 1 1 d . . . H6A H 0.3871 0.6570 0.1566 0.021 Uiso 1 1 calc R . . H6B H 0.3384 0.7436 0.0642 0.021 Uiso 1 1 calc R . . C7 C 0.33867(12) 1.1026(2) 0.20549(15) 0.0219(4) Uani 1 1 d . . . H7A H 0.2896 1.1071 0.1770 0.033 Uiso 1 1 calc R . . H7B H 0.3538 1.2106 0.2006 0.033 Uiso 1 1 calc R . . H7C H 0.3642 1.0750 0.2663 0.033 Uiso 1 1 calc R . . C8 C 0.40069(11) 1.0150(3) 0.15072(14) 0.0232(4) Uani 1 1 d . . . H8A H 0.4290 0.9174 0.1639 0.035 Uiso 1 1 calc R . . H8B H 0.4300 1.1064 0.1886 0.035 Uiso 1 1 calc R . . H8C H 0.3763 1.0472 0.0907 0.035 Uiso 1 1 calc R . . C9 C 0.30027(11) 0.5098(3) 0.26224(13) 0.0228(4) Uani 1 1 d . . . H9A H 0.2955 0.5930 0.2939 0.034 Uiso 1 1 calc R . . H9B H 0.3482 0.5043 0.2856 0.034 Uiso 1 1 calc R . . H9C H 0.2860 0.4016 0.2682 0.034 Uiso 1 1 calc R . . O1W O 0.5000 0.4495(3) 0.2500 0.0450(7) Uani 1 2 d S . . H1WA H 0.5066 0.5127 0.2218 0.068 Uiso 1 1 d 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 Br1 0.01816(11) 0.02646(11) 0.01728(10) -0.00337(8) 0.00834(9) 0.00000(8) Ge1 0.01228(10) 0.01415(10) 0.01436(10) 0.00158(7) 0.00859(8) 0.00146(7) S1 0.0133(2) 0.0138(2) 0.0267(3) -0.00276(19) 0.0107(2) 0.00056(18) S2 0.0201(2) 0.0185(2) 0.0211(2) -0.00288(19) 0.0153(2) -0.00059(19) O1 0.0148(7) 0.0149(7) 0.0234(7) 0.0008(6) 0.0118(6) 0.0014(5) O2 0.0167(7) 0.0158(6) 0.0200(7) 0.0004(5) 0.0135(6) 0.0000(5) N1 0.0164(8) 0.0156(8) 0.0195(8) -0.0033(6) 0.0125(7) -0.0010(6) N2 0.0141(8) 0.0172(8) 0.0170(8) 0.0031(6) 0.0104(7) 0.0010(6) C1 0.0155(9) 0.0158(9) 0.0160(9) 0.0010(7) 0.0115(8) 0.0007(7) C2 0.0146(9) 0.0161(9) 0.0254(10) -0.0038(8) 0.0128(9) -0.0015(7) C3 0.0280(12) 0.0166(10) 0.0425(14) -0.0064(9) 0.0245(11) 0.0009(9) C4 0.0192(11) 0.0238(10) 0.0302(12) -0.0094(9) 0.0147(10) -0.0043(9) C5 0.0110(8) 0.0171(9) 0.0123(8) 0.0035(7) 0.0060(7) 0.0030(7) C6 0.0179(10) 0.0180(9) 0.0198(9) 0.0029(8) 0.0136(9) 0.0020(8) C7 0.0244(11) 0.0150(9) 0.0300(11) -0.0026(8) 0.0188(10) -0.0005(8) C8 0.0211(11) 0.0273(11) 0.0253(11) -0.0004(9) 0.0165(9) -0.0060(9) C9 0.0201(10) 0.0283(11) 0.0168(10) 0.0058(8) 0.0101(9) 0.0002(9) O1W 0.0489(18) 0.0406(16) 0.0443(16) 0.000 0.0286(15) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Ge1 C9 1.917(2) . ? Ge1 O2 2.0145(14) . ? Ge1 O1 2.0395(14) . ? Ge1 S1 2.2092(5) . ? Ge1 S2 2.2117(5) . ? S1 C2 1.807(2) . ? S2 C6 1.818(2) . ? O1 C1 1.274(2) . ? O2 C5 1.277(2) . ? N1 C1 1.311(2) . ? N1 C3 1.460(3) . ? N1 C4 1.476(3) . ? N2 C5 1.310(3) . ? N2 C8 1.463(3) . ? N2 C7 1.466(3) . ? C1 C2 1.503(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.504(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? O1W H1WA 0.8500 . ? 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 C9 Ge1 O2 95.82(8) . . ? C9 Ge1 O1 98.46(8) . . ? O2 Ge1 O1 165.69(6) . . ? C9 Ge1 S1 119.10(7) . . ? O2 Ge1 S1 87.21(4) . . ? O1 Ge1 S1 86.61(4) . . ? C9 Ge1 S2 119.17(7) . . ? O2 Ge1 S2 86.96(4) . . ? O1 Ge1 S2 85.34(4) . . ? S1 Ge1 S2 121.74(2) . . ? C2 S1 Ge1 99.41(7) . . ? C6 S2 Ge1 97.31(7) . . ? C1 O1 Ge1 118.95(13) . . ? C5 O2 Ge1 118.46(12) . . ? C1 N1 C3 120.07(18) . . ? C1 N1 C4 122.34(17) . . ? C3 N1 C4 117.60(17) . . ? C5 N2 C8 122.40(17) . . ? C5 N2 C7 120.00(17) . . ? C8 N2 C7 117.36(17) . . ? O1 C1 N1 120.71(18) . . ? O1 C1 C2 120.14(17) . . ? N1 C1 C2 119.15(17) . . ? C1 C2 S1 112.12(14) . . ? C1 C2 H2A 109.2 . . ? S1 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? S1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 N2 119.97(18) . . ? O2 C5 C6 120.42(17) . . ? N2 C5 C6 119.60(17) . . ? C5 C6 S2 112.03(14) . . ? C5 C6 H6A 109.2 . . ? S2 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? S2 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? Ge1 C9 H9A 109.5 . . ? Ge1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? Ge1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 Ge1 S1 C2 -90.46(11) . . . . ? O2 Ge1 S1 C2 174.43(8) . . . . ? O1 Ge1 S1 C2 7.35(8) . . . . ? S2 Ge1 S1 C2 89.73(8) . . . . ? C9 Ge1 S2 C6 -77.49(10) . . . . ? O2 Ge1 S2 C6 17.49(8) . . . . ? O1 Ge1 S2 C6 -174.59(8) . . . . ? S1 Ge1 S2 C6 102.32(7) . . . . ? C9 Ge1 O1 C1 120.42(15) . . . . ? O2 Ge1 O1 C1 -63.1(3) . . . . ? S1 Ge1 O1 C1 1.49(13) . . . . ? S2 Ge1 O1 C1 -120.76(14) . . . . ? C9 Ge1 O2 C5 104.26(15) . . . . ? O1 Ge1 O2 C5 -72.3(3) . . . . ? S1 Ge1 O2 C5 -136.76(14) . . . . ? S2 Ge1 O2 C5 -14.76(13) . . . . ? Ge1 O1 C1 N1 167.23(14) . . . . ? Ge1 O1 C1 C2 -12.9(2) . . . . ? C3 N1 C1 O1 -2.5(3) . . . . ? C4 N1 C1 O1 177.41(19) . . . . ? C3 N1 C1 C2 177.61(19) . . . . ? C4 N1 C1 C2 -2.5(3) . . . . ? O1 C1 C2 S1 19.4(2) . . . . ? N1 C1 C2 S1 -160.75(15) . . . . ? Ge1 S1 C2 C1 -14.95(15) . . . . ? Ge1 O2 C5 N2 -175.90(13) . . . . ? Ge1 O2 C5 C6 3.3(2) . . . . ? C8 N2 C5 O2 178.04(18) . . . . ? C7 N2 C5 O2 3.7(3) . . . . ? C8 N2 C5 C6 -1.2(3) . . . . ? C7 N2 C5 C6 -175.47(18) . . . . ? O2 C5 C6 S2 14.0(2) . . . . ? N2 C5 C6 S2 -166.80(14) . . . . ? Ge1 S2 C6 C5 -20.89(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1W H1WA Br1 0.85 2.62 3.4645(17) 171 3_555 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.576 _refine_diff_density_min -0.558 _refine_diff_density_rms 0.093