# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_str1234 #TrackingRef '19749_web_deposit_cif_file_0_DavidRecatala_1366729890.str1234.cif' _audit_creation_date 2013-04-22 _audit_creation_method ; Olex2 1.2-alpha (compiled 2011.12.05 svn.r2101, GUI svn.r3974) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C28 H16 Mo2 N4 O2 S10, 2(C8 H20 N)' _chemical_formula_sum 'C44 H56 Mo2 N6 O2 S10' _chemical_formula_weight 1213.43 _chemical_melting_point ? _chemical_oxdiff_formula 'C44 H56 O2 S10 N6 Mo2' 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' Mo Mo -1.6832 0.6857 '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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.411(2) _cell_length_b 9.4996(4) _cell_length_c 21.3573(15) _cell_angle_alpha 90.00 _cell_angle_beta 114.965(9) _cell_angle_gamma 90.00 _cell_volume 5409.7(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6896 _cell_measurement_temperature 220.0 _cell_measurement_theta_max 29.3451 _cell_measurement_theta_min 2.8668 _exptl_absorpt_coefficient_mu 0.891 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_correction_T_min 0.958 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 2488 _exptl_crystal_size_max 0.4411 _exptl_crystal_size_mid 0.0638 _exptl_crystal_size_min 0.0272 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0795 _diffrn_reflns_av_unetI/netI 0.0792 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 31083 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.41 _diffrn_reflns_theta_min 2.87 _diffrn_ambient_temperature 220.0 _diffrn_detector_area_resol_mean 10.4051 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.918 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -99.00 61.00 1.0000 22.0000 omega____ theta____ kappa____ phi______ frames - -11.5596 0.0000 60.0000 160 #__ type_ start__ end____ width___ exp.time_ 2 omega 66.00 91.00 1.0000 22.0000 omega____ theta____ kappa____ phi______ frames - 12.2627 77.0000 30.0000 25 #__ type_ start__ end____ width___ exp.time_ 3 omega 14.00 41.00 1.0000 22.0000 omega____ theta____ kappa____ phi______ frames - 12.2627 77.0000 30.0000 27 #__ type_ start__ end____ width___ exp.time_ 4 omega -14.00 24.00 1.0000 22.0000 omega____ theta____ kappa____ phi______ frames - 12.2627 37.0000 150.0000 38 #__ type_ start__ end____ width___ exp.time_ 5 omega -88.00 15.00 1.0000 22.0000 omega____ theta____ kappa____ phi______ frames - -11.5596 -37.0000 -120.0000 103 #__ type_ start__ end____ width___ exp.time_ 6 omega -38.00 19.00 1.0000 22.0000 omega____ theta____ kappa____ phi______ frames - -11.5596 37.0000 -120.0000 57 #__ type_ start__ end____ width___ exp.time_ 7 omega -74.00 -29.00 1.0000 22.0000 omega____ theta____ kappa____ phi______ frames - -11.5596 133.0000 95.0000 45 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0185296000 _diffrn_orient_matrix_UB_12 -0.0520297000 _diffrn_orient_matrix_UB_13 0.0162801000 _diffrn_orient_matrix_UB_21 0.0080034000 _diffrn_orient_matrix_UB_22 0.0054951000 _diffrn_orient_matrix_UB_23 -0.0269340000 _diffrn_orient_matrix_UB_31 0.0173347000 _diffrn_orient_matrix_UB_32 0.0532438000 _diffrn_orient_matrix_UB_33 0.0187443000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4140 _reflns_number_total 6874 _reflns_odcompleteness_completeness 99.78 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 1.564 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.103 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 293 _refine_ls_number_reflns 6874 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1168 _refine_ls_R_factor_gt 0.0598 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+14.5716P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1193 _refine_ls_wR_factor_ref 0.1510 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H14 of C14, H9 of C9, {H10M,H10N} of C107, H7 of C7, {H10K,H10L} of C103, H12 of C12, H8 of C8, {H10I,H10J} of C101, H11 of C11, H6 of C6, H13 of C13, {H10G,H10H} of C105 At 1.5 times of: {H10A,H10B,H10C} of C104, {H10D,H10E,H10F} of C106, {H10R,H10S,H10T} of C102, {H10O,H10P,H10Q} of C108 2.a Secondary CH2 refined with riding coordinates: C105(H10G,H10H), C101(H10I,H10J), C103(H10K,H10L), C107(H10M,H10N) 2.b Aromatic/amide H refined with riding coordinates: C14(H14), C9(H9), C13(H13), C6(H6), C11(H11), C8(H8), C12(H12), C7(H7) 2.c Idealised Me refined as rotating group: C104(H10A,H10B,H10C), C106(H10D,H10E,H10F), C108(H10O,H10P,H10Q), C102(H10R, H10S,H10T) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _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 Mo1 Mo 0.470912(15) 0.98845(4) 0.67730(2) 0.04146(15) Uani 1 1 d . . . S5 S 0.42648(5) 0.79855(14) 0.43971(7) 0.0508(3) Uani 1 1 d . . . S4 S 0.33143(5) 0.82552(13) 0.45479(7) 0.0498(3) Uani 1 1 d . . . S1 S 0.55590(5) 0.93668(14) 0.73729(7) 0.0481(3) Uani 1 1 d . . . S2 S 0.38623(5) 0.90416(14) 0.60637(7) 0.0510(3) Uani 1 1 d . . . S3 S 0.48951(5) 0.88275(15) 0.58753(7) 0.0536(3) Uani 1 1 d . . . N2 N 0.37943(17) 0.4871(4) 0.3233(2) 0.0551(11) Uani 1 1 d . . . C10 C 0.37301(18) 0.6262(5) 0.3141(2) 0.0441(11) Uani 1 1 d . . . N100 N 0.36371(18) 0.3659(5) 0.5024(2) 0.0610(12) Uani 1 1 d . . . C4 C 0.33962(18) 0.6904(5) 0.3441(3) 0.0447(11) Uani 1 1 d . . . N1 N 0.25773(17) 0.7194(5) 0.3392(2) 0.0586(12) Uani 1 1 d . . . C5 C 0.28612(19) 0.6589(5) 0.3106(3) 0.0472(12) Uani 1 1 d . . . C3 C 0.36134(18) 0.7625(5) 0.4035(3) 0.0450(11) Uani 1 1 d . . . C2 C 0.43038(19) 0.8558(5) 0.5200(3) 0.0467(12) Uani 1 1 d . . . C14 C 0.4096(2) 0.4254(6) 0.2995(3) 0.0662(16) Uani 1 1 d . . . H14 H 0.4143 0.3286 0.3054 0.079 Uiso 1 1 calc R . . C1 C 0.38784(19) 0.8656(5) 0.5268(3) 0.0470(12) Uani 1 1 d . . . C104 C 0.2725(3) 0.3118(8) 0.4173(4) 0.099(2) Uani 1 1 d . . . H10A H 0.2471 0.3407 0.3735 0.148 Uiso 1 1 calc R . . H10B H 0.2597 0.3181 0.4518 0.148 Uiso 1 1 calc R . . H10C H 0.2821 0.2163 0.4142 0.148 Uiso 1 1 calc R . . C9 C 0.2091(2) 0.6891(7) 0.3121(3) 0.0730(17) Uani 1 1 d . . . H9 H 0.1898 0.7280 0.3327 0.088 Uiso 1 1 calc R . . C106 C 0.3305(4) 0.4900(8) 0.5805(4) 0.110(3) Uani 1 1 d . . . H10D H 0.2992 0.5122 0.5423 0.165 Uiso 1 1 calc R . . H10E H 0.3536 0.5662 0.5879 0.165 Uiso 1 1 calc R . . H10F H 0.3250 0.4762 0.6213 0.165 Uiso 1 1 calc R . . C105 C 0.3519(3) 0.3568(7) 0.5647(3) 0.0771(18) Uani 1 1 d . . . H10G H 0.3824 0.3327 0.6047 0.093 Uiso 1 1 calc R . . H10H H 0.3282 0.2809 0.5574 0.093 Uiso 1 1 calc R . . C13 C 0.4343(2) 0.4954(7) 0.2667(3) 0.0670(16) Uani 1 1 d . . . H13 H 0.4548 0.4475 0.2506 0.080 Uiso 1 1 calc R . . C6 C 0.2647(2) 0.5705(6) 0.2532(3) 0.0593(14) Uani 1 1 d . . . H6 H 0.2844 0.5296 0.2337 0.071 Uiso 1 1 calc R . . C11 C 0.3962(2) 0.7038(6) 0.2818(3) 0.0572(14) Uani 1 1 d . . . H11 H 0.3906 0.8002 0.2756 0.069 Uiso 1 1 calc R . . C101 C 0.3822(2) 0.2209(6) 0.4938(3) 0.0712(17) Uani 1 1 d . . . H10I H 0.4106 0.1962 0.5364 0.085 Uiso 1 1 calc R . . H10J H 0.3558 0.1532 0.4868 0.085 Uiso 1 1 calc R . . C8 C 0.1854(2) 0.6039(7) 0.2553(4) 0.0796(19) Uani 1 1 d . . . H8 H 0.1511 0.5871 0.2375 0.095 Uiso 1 1 calc R . . C12 C 0.4278(2) 0.6373(7) 0.2588(3) 0.0706(18) Uani 1 1 d . . . H12 H 0.4445 0.6887 0.2379 0.085 Uiso 1 1 calc R . . C103 C 0.3180(2) 0.4069(6) 0.4372(3) 0.0662(16) Uani 1 1 d . . . H10K H 0.3082 0.5017 0.4431 0.079 Uiso 1 1 calc R . . H10L H 0.3276 0.4091 0.3990 0.079 Uiso 1 1 calc R . . C7 C 0.2142(2) 0.5450(6) 0.2263(4) 0.0728(18) Uani 1 1 d . . . H7 H 0.1994 0.4870 0.1878 0.087 Uiso 1 1 calc R . . C107 C 0.4029(2) 0.4767(6) 0.5116(3) 0.0689(17) Uani 1 1 d . . . H10M H 0.4082 0.4801 0.4698 0.083 Uiso 1 1 calc R . . H10N H 0.3896 0.5674 0.5166 0.083 Uiso 1 1 calc R . . C108 C 0.4530(3) 0.4559(8) 0.5721(4) 0.113(3) Uani 1 1 d . . . H10O H 0.4672 0.3679 0.5672 0.170 Uiso 1 1 calc R . . H10P H 0.4485 0.4550 0.6141 0.170 Uiso 1 1 calc R . . H10Q H 0.4751 0.5314 0.5736 0.170 Uiso 1 1 calc R . . C102 C 0.3977(3) 0.2063(7) 0.4353(4) 0.097(2) Uani 1 1 d . . . H10R H 0.3711 0.2392 0.3933 0.145 Uiso 1 1 calc R . . H10S H 0.4045 0.1092 0.4302 0.145 Uiso 1 1 calc R . . H10T H 0.4273 0.2613 0.4451 0.145 Uiso 1 1 calc R . . O1 O 0.46548(13) 1.1627(3) 0.66060(17) 0.0528(9) 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 Mo1 0.0431(3) 0.0362(2) 0.0437(3) -0.00208(18) 0.01702(19) -0.00151(18) S5 0.0465(7) 0.0540(8) 0.0520(8) -0.0116(6) 0.0207(6) -0.0075(6) S4 0.0441(7) 0.0486(7) 0.0546(8) -0.0049(6) 0.0188(6) -0.0011(6) S1 0.0418(7) 0.0544(7) 0.0478(7) -0.0076(6) 0.0187(6) -0.0001(6) S2 0.0450(7) 0.0575(8) 0.0514(8) -0.0053(6) 0.0211(6) -0.0058(6) S3 0.0427(7) 0.0638(8) 0.0528(8) -0.0160(7) 0.0187(6) -0.0041(6) N2 0.057(3) 0.047(3) 0.070(3) 0.007(2) 0.034(2) 0.005(2) C10 0.044(3) 0.044(3) 0.039(3) -0.001(2) 0.012(2) -0.008(2) N100 0.069(3) 0.055(3) 0.054(3) 0.008(2) 0.021(2) -0.006(2) C4 0.046(3) 0.035(2) 0.050(3) 0.002(2) 0.017(2) -0.003(2) N1 0.048(3) 0.062(3) 0.064(3) -0.007(2) 0.021(2) -0.002(2) C5 0.044(3) 0.040(3) 0.050(3) 0.004(2) 0.013(2) 0.000(2) C3 0.047(3) 0.035(2) 0.052(3) 0.004(2) 0.021(2) 0.000(2) C2 0.048(3) 0.044(3) 0.048(3) -0.008(2) 0.020(2) -0.007(2) C14 0.072(4) 0.062(4) 0.076(4) 0.001(3) 0.042(4) 0.007(3) C1 0.048(3) 0.038(3) 0.055(3) -0.005(2) 0.023(3) -0.003(2) C104 0.074(5) 0.113(6) 0.094(6) 0.013(5) 0.022(4) -0.015(4) C9 0.050(4) 0.081(4) 0.088(5) -0.009(4) 0.029(3) 0.002(3) C106 0.152(9) 0.102(6) 0.095(6) -0.007(5) 0.071(6) 0.011(5) C105 0.100(5) 0.071(4) 0.065(4) 0.004(3) 0.039(4) -0.012(4) C13 0.058(4) 0.092(5) 0.058(4) -0.009(3) 0.031(3) 0.001(3) C6 0.049(3) 0.054(3) 0.068(4) -0.014(3) 0.018(3) -0.006(3) C11 0.071(4) 0.052(3) 0.052(3) -0.002(3) 0.030(3) -0.018(3) C101 0.075(4) 0.053(3) 0.076(4) 0.015(3) 0.023(4) 0.003(3) C8 0.048(4) 0.087(5) 0.098(5) -0.018(4) 0.025(4) -0.013(3) C12 0.076(4) 0.093(5) 0.055(4) -0.008(3) 0.039(3) -0.034(4) C103 0.063(4) 0.065(4) 0.064(4) 0.014(3) 0.022(3) 0.003(3) C7 0.052(4) 0.064(4) 0.087(5) -0.022(3) 0.014(3) -0.014(3) C107 0.068(4) 0.050(3) 0.073(4) 0.019(3) 0.014(3) -0.009(3) C108 0.083(5) 0.089(5) 0.117(7) 0.037(5) -0.008(5) -0.023(4) C102 0.122(7) 0.071(4) 0.125(7) 0.023(4) 0.079(6) 0.026(4) O1 0.067(2) 0.0382(18) 0.051(2) 0.0028(15) 0.0228(19) 0.0006(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 Mo1 Mo1 2.8435(9) 2_656 ? Mo1 S1 2.3249(13) 2_656 ? Mo1 S1 2.3297(14) . ? Mo1 S2 2.4401(14) . ? Mo1 S3 2.4225(14) . ? Mo1 O1 1.687(3) . ? S5 C3 1.771(5) . ? S5 C2 1.756(5) . ? S4 C3 1.773(5) . ? S4 C1 1.763(5) . ? S1 Mo1 2.3249(13) 2_656 ? S2 C1 1.759(5) . ? S3 C2 1.747(5) . ? N2 C10 1.337(6) . ? N2 C14 1.331(7) . ? C10 C4 1.509(7) . ? C10 C11 1.371(6) . ? N100 C105 1.512(7) . ? N100 C101 1.521(7) . ? N100 C103 1.523(7) . ? N100 C107 1.510(7) . ? C4 C5 1.458(7) . ? C4 C3 1.343(7) . ? N1 C5 1.354(6) . ? N1 C9 1.329(7) . ? C5 C6 1.397(7) . ? C2 C1 1.321(7) . ? C14 C13 1.374(8) . ? C104 C103 1.518(8) . ? C9 C8 1.377(8) . ? C106 C105 1.514(9) . ? C13 C12 1.362(8) . ? C6 C7 1.369(8) . ? C11 C12 1.376(8) . ? C101 C102 1.506(8) . ? C8 C7 1.363(8) . ? C107 C108 1.508(9) . ? 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 Mo1 Mo1 52.27(3) . 2_656 ? S1 Mo1 Mo1 52.42(3) 2_656 2_656 ? S1 Mo1 S1 99.46(5) 2_656 . ? S1 Mo1 S2 148.12(5) . . ? S1 Mo1 S2 79.77(5) 2_656 . ? S1 Mo1 S3 142.93(5) 2_656 . ? S1 Mo1 S3 78.43(5) . . ? S2 Mo1 Mo1 131.61(4) . 2_656 ? S3 Mo1 Mo1 129.16(4) . 2_656 ? S3 Mo1 S2 83.39(5) . . ? O1 Mo1 Mo1 100.99(12) . 2_656 ? O1 Mo1 S1 107.90(13) . . ? O1 Mo1 S1 109.89(12) . 2_656 ? O1 Mo1 S2 102.12(13) . . ? O1 Mo1 S3 105.80(12) . . ? C2 S5 C3 95.7(2) . . ? C1 S4 C3 94.7(2) . . ? Mo1 S1 Mo1 75.31(4) 2_656 . ? C1 S2 Mo1 103.39(17) . . ? C2 S3 Mo1 103.60(17) . . ? C14 N2 C10 117.1(5) . . ? N2 C10 C4 114.5(4) . . ? N2 C10 C11 122.4(5) . . ? C11 C10 C4 123.1(5) . . ? C105 N100 C101 106.4(4) . . ? C105 N100 C103 112.1(5) . . ? C101 N100 C103 110.1(4) . . ? C107 N100 C105 111.8(5) . . ? C107 N100 C101 110.8(5) . . ? C107 N100 C103 105.8(4) . . ? C5 C4 C10 118.0(4) . . ? C3 C4 C10 118.2(4) . . ? C3 C4 C5 123.6(5) . . ? C9 N1 C5 117.9(5) . . ? N1 C5 C4 115.8(4) . . ? N1 C5 C6 121.0(5) . . ? C6 C5 C4 123.2(5) . . ? S5 C3 S4 113.1(3) . . ? C4 C3 S5 120.4(4) . . ? C4 C3 S4 126.4(4) . . ? S3 C2 S5 118.9(3) . . ? C1 C2 S5 117.0(4) . . ? C1 C2 S3 123.9(4) . . ? N2 C14 C13 124.2(6) . . ? S2 C1 S4 119.2(3) . . ? C2 C1 S4 118.4(4) . . ? C2 C1 S2 122.2(4) . . ? N1 C9 C8 124.1(6) . . ? N100 C105 C106 114.9(5) . . ? C12 C13 C14 117.7(6) . . ? C7 C6 C5 118.8(5) . . ? C10 C11 C12 119.2(5) . . ? C102 C101 N100 115.7(5) . . ? C7 C8 C9 117.5(6) . . ? C13 C12 C11 119.4(5) . . ? C104 C103 N100 115.9(5) . . ? C8 C7 C6 120.5(6) . . ? C108 C107 N100 115.8(5) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -30 0 -10 0.0232 -30.0002 0.0000 -10.0000 -0.7187 0.0292 -0.7075 30 0 10 0.0406 30.0002 -0.0000 10.0000 0.7187 -0.0292 0.7075 8 -13 1 0.2028 8.0000 -13.0000 1.0000 0.8409 -0.0343 -0.5347 -6 13 0 0.2170 -6.0000 13.0000 0.0000 -0.7876 0.0234 0.5882 31 0 -28 0.0262 30.9999 0.0000 -28.0000 0.1186 1.0023 0.0125 -31 0 28 0.0010 -30.9999 -0.0000 28.0000 -0.1186 -1.0023 -0.0125 _database_code_depnum_ccdc_archive 'CCDC 935738' ####################################################################### # # 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_exp_458 #TrackingRef '19775_web_deposit_cif_file_0_DavidRecatala_1366793746.exp_458.cif' _audit_creation_date 2013-04-24 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C16 H14 N2 S4 Sn, C4 O' _chemical_formula_sum 'C20 H15 N2 O S4 Sn' _chemical_formula_weight 546.27 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula 'C16 H14 N2 S4 Sn' 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' Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' _cell_length_a 6.90185(15) _cell_length_b 15.7670(4) _cell_length_c 10.3916(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.706(2) _cell_angle_gamma 90.00 _cell_volume 1128.46(5) _cell_formula_units_Z 2 _cell_measurement_reflns_used 7089 _cell_measurement_temperature 199.95(10) _cell_measurement_theta_max 28.8509 _cell_measurement_theta_min 2.9514 _exptl_absorpt_coefficient_mu 1.515 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.70123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 542 _exptl_crystal_size_max 0.429 _exptl_crystal_size_mid 0.196 _exptl_crystal_size_min 0.085 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_unetI/netI 0.0417 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 12798 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 28.91 _diffrn_reflns_theta_min 2.96 _diffrn_ambient_temperature 199.95(10) _diffrn_detector_area_resol_mean 10.4051 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.929 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -55.00 48.00 0.5000 2.0000 omega____ theta____ kappa____ phi______ frames - 16.5978 -57.0000 0.0000 206 #__ type_ start__ end____ width___ exp.time_ 2 omega -73.00 44.00 0.5000 2.0000 omega____ theta____ kappa____ phi______ frames - 16.5978 -77.0000 120.0000 234 #__ type_ start__ end____ width___ exp.time_ 3 omega 35.00 80.00 0.5000 2.0000 omega____ theta____ kappa____ phi______ frames - -15.9728 178.0000 0.0000 90 #__ type_ start__ end____ width___ exp.time_ 4 omega 35.00 113.00 0.5000 2.0000 omega____ theta____ kappa____ phi______ frames - 16.5978 178.0000 -30.0000 156 #__ type_ start__ end____ width___ exp.time_ 5 omega -21.00 28.00 0.5000 2.0000 omega____ theta____ kappa____ phi______ frames - 16.5978 38.0000 0.0000 98 #__ type_ start__ end____ width___ exp.time_ 6 omega -20.00 101.00 0.5000 2.0000 omega____ theta____ kappa____ phi______ frames - 16.5978 57.0000 120.0000 242 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0103943000 _diffrn_orient_matrix_UB_12 -0.0010617000 _diffrn_orient_matrix_UB_13 -0.0683590000 _diffrn_orient_matrix_UB_21 -0.1001395000 _diffrn_orient_matrix_UB_22 0.0095206000 _diffrn_orient_matrix_UB_23 0.0021412000 _diffrn_orient_matrix_UB_31 0.0214508000 _diffrn_orient_matrix_UB_32 0.0439525000 _diffrn_orient_matrix_UB_33 -0.0020168000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4811 _reflns_number_total 5281 _reflns_odcompleteness_completeness 99.83 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.660 _refine_diff_density_min -0.818 _refine_diff_density_rms 0.074 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.058(18) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 264 _refine_ls_number_reflns 5281 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0338 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0386P)^2^+0.0089P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.0791 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H13 of C13, H16 of C16, H11 of C11, H15 of C15, H14 of C14, H8 of C8, H10 of C10, H9 of C9 At 1.5 times of: {H2A,H2B,H2C} of C2, {H1A,H1B,H1C} of C1 2. Others Fixed Sof: O1(0.614) O2(0.386) 3.a Aromatic/amide H refined with riding coordinates: C13(H13), C16(H16), C11(H11), C15(H15), C14(H14), C8(H8), C10(H10), C9(H9) 3.b Idealised Me refined as rotating group: C2(H2A,H2B,H2C), C1(H1A,H1B,H1C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _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 Sn1 Sn 0.22756(3) 0.286370(15) 0.29108(3) 0.03951(9) Uani 1 1 d . . . S3 S 0.59409(13) 0.43661(6) 0.64024(9) 0.0310(2) Uani 1 1 d . . . S4 S 0.72441(14) 0.50267(6) 0.39612(10) 0.0336(2) Uani 1 1 d . . . S2 S 0.42153(16) 0.41377(7) 0.22947(10) 0.0380(2) Uani 1 1 d . . . S1 S 0.27199(15) 0.33481(7) 0.51615(11) 0.0373(2) Uani 1 1 d . . . C3 C 0.4703(5) 0.4019(2) 0.4959(4) 0.0293(8) Uani 1 1 d . . . C4 C 0.5257(5) 0.4323(2) 0.3848(3) 0.0290(8) Uani 1 1 d . . . C5 C 0.7624(5) 0.5001(2) 0.5649(4) 0.0271(8) Uani 1 1 d . . . N1 N 0.8179(5) 0.5019(2) 0.8344(3) 0.0399(8) Uani 1 1 d . . . C2 C -0.0473(5) 0.3101(3) 0.1956(4) 0.0416(11) Uani 1 1 d . . . H2A H -0.1296 0.3376 0.2538 0.062 Uiso 1 1 calc R . . H2B H -0.1051 0.2574 0.1672 0.062 Uiso 1 1 calc R . . H2C H -0.0318 0.3460 0.1224 0.062 Uiso 1 1 calc R . . C6 C 0.9095(5) 0.5451(2) 0.6268(4) 0.0281(8) Uani 1 1 d . . . C13 C 1.1487(5) 0.5677(3) 0.4585(5) 0.0384(10) Uani 1 1 d . . . H13 H 1.1538 0.5094 0.4461 0.046 Uiso 1 1 calc R . . C12 C 1.0304(5) 0.6013(2) 0.5490(4) 0.0299(8) Uani 1 1 d . . . C7 C 0.9544(6) 0.5389(2) 0.7658(4) 0.0345(9) Uani 1 1 d . . . N2 N 1.0214(4) 0.68573(19) 0.5698(3) 0.0293(7) Uani 1 1 d . . . C16 C 1.1338(5) 0.7358(2) 0.5025(4) 0.0346(9) Uani 1 1 d . . . H16 H 1.1312 0.7938 0.5182 0.042 Uiso 1 1 calc R . . C11 C 0.8553(8) 0.4936(3) 0.9625(5) 0.0514(12) Uani 1 1 d . . . H11 H 0.7619 0.4682 1.0104 0.062 Uiso 1 1 calc R . . C15 C 1.2533(6) 0.7065(3) 0.4112(5) 0.0427(10) Uani 1 1 d . . . H15 H 1.3290 0.7438 0.3666 0.051 Uiso 1 1 calc R . . C14 C 1.2581(6) 0.6206(3) 0.3875(5) 0.0427(10) Uani 1 1 d . . . H14 H 1.3340 0.5989 0.3245 0.051 Uiso 1 1 calc R . . C8 C 1.1290(7) 0.5670(3) 0.8248(5) 0.0505(12) Uani 1 1 d . . . H8 H 1.2214 0.5925 0.7762 0.061 Uiso 1 1 calc R . . C10 C 1.0243(8) 0.5207(3) 1.0258(5) 0.0600(14) Uani 1 1 d . . . H10 H 1.0437 0.5147 1.1148 0.072 Uiso 1 1 calc R . . C1 C 0.4251(6) 0.1852(3) 0.2696(5) 0.0448(12) Uani 1 1 d . . . H1A H 0.5437 0.2070 0.2390 0.067 Uiso 1 1 calc R . . H1B H 0.3692 0.1449 0.2086 0.067 Uiso 1 1 calc R . . H1C H 0.4519 0.1578 0.3513 0.067 Uiso 1 1 calc R . . C9 C 1.1641(8) 0.5568(4) 0.9557(6) 0.0692(17) Uani 1 1 d . . . H9 H 1.2815 0.5742 0.9961 0.083 Uiso 1 1 calc R . . C19 C 0.448(3) 0.2057(9) 0.8727(12) 0.180(6) Uani 1 1 d . A . C18 C 0.4659(18) 0.2873(10) 0.9414(11) 0.165(4) Uani 1 1 d . . . O1 O 0.2741(10) 0.2865(6) 1.0074(6) 0.085(2) Uani 0.61 1 d P A 1 O2 O 0.301(3) 0.3330(9) 0.9001(13) 0.107(5) Uani 0.39 1 d P A 2 C20 C 0.229(3) 0.2037(8) 0.8230(10) 0.197(9) Uani 1 1 d . . . C21 C 0.141(2) 0.2605(14) 0.8890(17) 0.262(11) Uani 1 1 d . A . 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 Sn1 0.02871(12) 0.02797(13) 0.05980(19) -0.01338(15) -0.01282(11) 0.00378(12) S3 0.0303(5) 0.0259(5) 0.0362(5) 0.0018(4) -0.0026(4) -0.0083(4) S4 0.0301(5) 0.0335(5) 0.0368(5) -0.0001(4) -0.0003(4) -0.0085(4) S2 0.0407(5) 0.0346(6) 0.0375(6) -0.0039(5) -0.0067(4) -0.0051(5) S1 0.0343(5) 0.0303(5) 0.0468(6) 0.0018(4) -0.0023(4) -0.0125(4) C3 0.0270(17) 0.0212(19) 0.039(2) -0.0062(15) -0.0043(15) -0.0040(14) C4 0.0275(17) 0.0264(19) 0.0321(19) -0.0030(16) -0.0050(14) -0.0022(15) C5 0.0272(18) 0.0180(17) 0.035(2) 0.0021(15) -0.0032(15) -0.0004(15) N1 0.0407(19) 0.038(2) 0.040(2) 0.0056(16) -0.0089(15) -0.0047(16) C2 0.0257(17) 0.042(3) 0.055(3) 0.0121(19) -0.0108(17) -0.0016(16) C6 0.0258(17) 0.0164(17) 0.042(2) 0.0018(15) -0.0009(15) 0.0009(14) C13 0.0270(19) 0.0202(19) 0.068(3) -0.0052(19) 0.0050(19) 0.0005(16) C12 0.0197(16) 0.0226(18) 0.046(2) 0.0012(16) -0.0075(15) -0.0026(14) C7 0.0347(19) 0.0202(18) 0.047(2) 0.0024(17) -0.0100(17) -0.0017(16) N2 0.0231(14) 0.0216(15) 0.0424(19) 0.0022(14) -0.0033(13) -0.0030(12) C16 0.0281(18) 0.0209(19) 0.055(3) 0.0026(17) 0.0007(17) 0.0007(15) C11 0.062(3) 0.043(3) 0.047(3) 0.015(2) -0.008(2) -0.002(2) C15 0.033(2) 0.029(2) 0.067(3) 0.004(2) 0.007(2) -0.0060(17) C14 0.030(2) 0.036(2) 0.063(3) -0.004(2) 0.0118(19) -0.0002(18) C8 0.046(2) 0.048(3) 0.054(3) 0.011(2) -0.019(2) -0.014(2) C10 0.076(4) 0.053(3) 0.047(3) 0.012(2) -0.030(3) -0.010(3) C1 0.033(2) 0.033(2) 0.069(3) 0.001(2) 0.008(2) 0.0046(18) C9 0.066(3) 0.071(4) 0.066(4) 0.018(3) -0.037(3) -0.021(3) C19 0.278(16) 0.140(10) 0.119(8) -0.047(7) -0.006(10) 0.098(11) C18 0.175(10) 0.165(10) 0.148(9) -0.046(11) -0.043(8) 0.019(12) O1 0.085(4) 0.115(5) 0.054(3) -0.033(5) 0.005(3) -0.034(6) O2 0.164(15) 0.083(8) 0.076(9) 0.014(7) 0.016(9) 0.013(10) C20 0.40(3) 0.123(9) 0.069(6) -0.014(6) 0.038(10) -0.131(13) C21 0.167(12) 0.35(2) 0.271(18) -0.209(19) 0.035(12) -0.117(15) _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 Sn1 S2 2.5196(12) . ? Sn1 S1 2.4607(11) . ? Sn1 C2 2.116(4) . ? Sn1 C1 2.120(4) . ? S3 C3 1.764(4) . ? S3 C5 1.756(4) . ? S4 C4 1.762(4) . ? S4 C5 1.756(4) . ? S2 C4 1.749(4) . ? S1 C3 1.753(4) . ? C3 C4 1.329(5) . ? C5 C6 1.366(5) . ? N1 C7 1.350(5) . ? N1 C11 1.346(6) . ? C6 C12 1.491(5) . ? C6 C7 1.461(5) . ? C13 C12 1.389(6) . ? C13 C14 1.371(6) . ? C12 N2 1.351(5) . ? C7 C8 1.389(6) . ? N2 C16 1.336(5) . ? C16 C15 1.376(6) . ? C11 C10 1.370(7) . ? C15 C14 1.377(6) . ? C8 C9 1.375(7) . ? C10 C9 1.370(8) . ? C19 C18 1.473(17) . ? C19 C20 1.57(2) . ? C18 O1 1.529(14) . ? C18 O2 1.391(18) . ? O1 C21 1.541(15) . ? O2 C21 1.59(2) . ? C20 C21 1.30(2) . ? 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 Sn1 S2 87.62(3) . . ? C2 Sn1 S2 102.41(11) . . ? C2 Sn1 S1 116.34(13) . . ? C2 Sn1 C1 130.28(19) . . ? C1 Sn1 S2 102.55(12) . . ? C1 Sn1 S1 107.00(15) . . ? C5 S3 C3 95.48(18) . . ? C5 S4 C4 96.73(18) . . ? C4 S2 Sn1 95.28(13) . . ? C3 S1 Sn1 97.11(13) . . ? S1 C3 S3 115.1(2) . . ? C4 C3 S3 118.4(3) . . ? C4 C3 S1 126.3(3) . . ? S2 C4 S4 116.0(2) . . ? C3 C4 S4 115.8(3) . . ? C3 C4 S2 128.1(3) . . ? S3 C5 S4 113.5(2) . . ? C6 C5 S3 125.4(3) . . ? C6 C5 S4 121.1(3) . . ? C11 N1 C7 117.9(4) . . ? C5 C6 C12 118.6(3) . . ? C5 C6 C7 122.3(3) . . ? C7 C6 C12 119.1(3) . . ? C14 C13 C12 120.0(4) . . ? C13 C12 C6 121.0(3) . . ? N2 C12 C6 117.7(3) . . ? N2 C12 C13 121.3(4) . . ? N1 C7 C6 116.1(3) . . ? N1 C7 C8 121.3(4) . . ? C8 C7 C6 122.5(4) . . ? C16 N2 C12 117.6(3) . . ? N2 C16 C15 123.8(4) . . ? N1 C11 C10 123.2(5) . . ? C16 C15 C14 118.4(4) . . ? C13 C14 C15 118.7(4) . . ? C9 C8 C7 119.5(5) . . ? C11 C10 C9 118.7(4) . . ? C10 C9 C8 119.3(5) . . ? C18 C19 C20 103.2(10) . . ? C19 C18 O1 99.3(12) . . ? O2 C18 C19 105.1(11) . . ? O2 C18 O1 55.1(8) . . ? C18 O1 C21 97.6(7) . . ? C18 O2 C21 101.5(13) . . ? C21 C20 C19 106.4(11) . . ? O1 C21 O2 51.4(6) . . ? C20 C21 O1 109.4(16) . . ? C20 C21 O2 101.0(12) . . ? _database_code_depnum_ccdc_archive 'CCDC 935740'