# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Kathryn Preuss' _publ_contact_author_email kpreuss@uoguelph.ca loop_ _publ_author_name 'David S. Sullivan' 'Rodolphe Clerac' 'Michael Jennings' 'Alan J. Lough' 'Kathryn E. Preuss' data_k11159 _database_code_depnum_ccdc_archive 'CCDC 896030' #TrackingRef '- DaveMnTrimer_kplabels_mj.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H22 F36 Mn3 N2 O16 S4' _chemical_formula_sum 'C54 H22 F36 Mn3 N2 O16 S4' _chemical_formula_weight 1931.80 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' F F 0.0171 0.0103 '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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.178(2) _cell_length_b 12.716(3) _cell_length_c 12.809(3) _cell_angle_alpha 69.55(3) _cell_angle_beta 76.62(3) _cell_angle_gamma 68.97(3) _cell_volume 1722.0(6) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 19955 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.863 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 951 _exptl_absorpt_coefficient_mu 0.827 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.791 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; -CF3, ANISO, 56/44, SADI C-F ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 28760 _diffrn_reflns_av_R_equivalents 0.0903 _diffrn_reflns_av_sigmaI/netI 0.0702 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 25.02 _reflns_number_total 6083 _reflns_number_gt 4194 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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. One of the CF~3~ ligands was disordered and was modelled anisotropically at a 0.56/0.44 ratio. The ratio was determined by letting the occupancy refine. The six C-F bond lengths were restrained to be equivalent using the SADI command, this gave more realistic bond lengths then letting them refine freely. ; _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^)+(0.0461P)^2^+0.7058P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6083 _refine_ls_number_parameters 547 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0883 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.059 _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 Mn1 Mn 0.57620(5) -0.04267(4) 0.25840(5) 0.02932(17) Uani 1 1 d . . . Mn2 Mn 0.0000 0.5000 0.0000 0.0286(2) Uani 1 2 d S . . S1 S 0.27963(8) 0.24550(8) -0.02093(8) 0.0334(3) Uani 1 1 d . . . S2 S 0.45377(8) 0.14311(8) -0.00182(8) 0.0342(3) Uani 1 1 d . . . N1 N 0.4382(3) 0.0863(2) 0.1357(2) 0.0279(7) Uani 1 1 d . . . C1 C 0.3293(3) 0.1222(3) 0.1851(3) 0.0277(9) Uani 1 1 d . . . C2 C 0.3080(3) 0.0709(3) 0.3097(3) 0.0286(9) Uani 1 1 d . . . O1 O 0.3915(2) -0.0017(2) 0.3590(2) 0.0335(6) Uani 1 1 d . . . C3 C 0.1873(3) 0.1137(3) 0.3629(3) 0.0285(9) Uani 1 1 d . . . C4 C 0.1623(3) 0.0722(3) 0.4781(3) 0.0326(9) Uani 1 1 d . . . H4A H 0.2227 0.0136 0.5206 0.039 Uiso 1 1 calc R . . C5 C 0.0502(4) 0.1146(3) 0.5332(3) 0.0368(10) Uani 1 1 d . . . C11 C 0.0254(4) 0.0672(4) 0.6586(3) 0.0490(11) Uani 1 1 d . . . H11A H 0.0963 0.0056 0.6881 0.074 Uiso 1 1 calc R . . H11B H -0.0403 0.0340 0.6770 0.074 Uiso 1 1 calc R . . H11C H 0.0042 0.1312 0.6925 0.074 Uiso 1 1 calc R . . C6 C -0.0386(3) 0.2034(3) 0.4692(3) 0.0331(9) Uani 1 1 d . . . C12 C -0.1592(3) 0.2547(4) 0.5262(4) 0.0466(11) Uani 1 1 d . . . H12A H -0.2072 0.3188 0.4704 0.070 Uiso 1 1 calc R . . H12B H -0.1509 0.2856 0.5832 0.070 Uiso 1 1 calc R . . H12C H -0.1981 0.1933 0.5620 0.070 Uiso 1 1 calc R . . C7 C -0.0121(3) 0.2439(3) 0.3538(3) 0.0323(9) Uani 1 1 d . . . H7A H -0.0721 0.3036 0.3113 0.039 Uiso 1 1 calc R . . C8 C 0.0982(3) 0.2007(3) 0.2978(3) 0.0282(9) Uani 1 1 d . . . C9 C 0.1205(3) 0.2470(3) 0.1743(3) 0.0293(9) Uani 1 1 d . . . O2 O 0.0395(2) 0.3204(2) 0.1174(2) 0.0346(6) Uani 1 1 d . . . C10 C 0.2384(3) 0.2032(3) 0.1222(3) 0.0278(9) Uani 1 1 d . . . O21 O 0.6196(2) 0.0939(2) 0.2810(2) 0.0359(6) Uani 1 1 d . . . C22 C 0.6829(3) 0.1553(3) 0.2167(4) 0.0347(10) Uani 1 1 d . . . C23 C 0.7470(4) 0.1455(3) 0.1138(4) 0.0395(10) Uani 1 1 d . . . H23A H 0.7903 0.1994 0.0728 0.047 Uiso 1 1 calc R . . C24 C 0.7501(3) 0.0595(3) 0.0685(3) 0.0365(10) Uani 1 1 d . . . O25 O 0.6998(2) -0.0192(2) 0.1108(2) 0.0370(7) Uani 1 1 d . . . C26 C 0.6852(4) 0.2510(3) 0.2617(4) 0.0423(11) Uani 1 1 d . . . C27 C 0.8198(4) 0.0570(4) -0.0462(4) 0.0517(12) Uani 1 1 d . . . F21 F 0.7136(3) 0.2040(2) 0.3660(2) 0.0706(9) Uani 1 1 d . . . F22 F 0.5805(2) 0.3322(2) 0.2634(2) 0.0552(7) Uani 1 1 d . . . F23 F 0.7648(2) 0.3061(2) 0.2021(2) 0.0559(7) Uani 1 1 d . . . F24 F 0.8699(3) 0.1426(3) -0.0945(2) 0.0832(10) Uani 1 1 d . . . F25 F 0.7508(3) 0.0655(2) -0.1180(2) 0.0662(8) Uani 1 1 d . . . F26 F 0.9061(2) -0.0446(3) -0.0407(3) 0.0744(9) Uani 1 1 d . . . O31 O 0.6503(2) -0.1608(2) 0.4064(2) 0.0323(6) Uani 1 1 d . . . C32 C 0.6403(3) -0.2606(3) 0.4568(3) 0.0299(9) Uani 1 1 d . . . C33 C 0.5901(3) -0.3246(3) 0.4232(3) 0.0349(9) Uani 1 1 d . . . H33A H 0.5817 -0.3970 0.4743 0.042 Uiso 1 1 calc R . . C34 C 0.5521(3) -0.2873(3) 0.3192(3) 0.0314(9) Uani 1 1 d . A . O35 O 0.5539(2) -0.1938(2) 0.2407(2) 0.0315(6) Uani 1 1 d . . . C36 C 0.6950(4) -0.3198(3) 0.5681(3) 0.0387(10) Uani 1 1 d . . . C37 C 0.5013(4) -0.3662(4) 0.2899(4) 0.0471(12) Uani 1 1 d D . . F31 F 0.6869(2) -0.4280(2) 0.6190(2) 0.0604(8) Uani 1 1 d . . . F32 F 0.6425(2) -0.2566(2) 0.64004(19) 0.0510(6) Uani 1 1 d . . . F33 F 0.8100(2) -0.32780(19) 0.5504(2) 0.0453(6) Uani 1 1 d . . . F34A F 0.3958(8) -0.3046(12) 0.2567(12) 0.073(4) Uani 0.56 1 d PD A 1 F35A F 0.489(3) -0.4597(13) 0.3699(12) 0.088(5) Uani 0.56 1 d PD A 1 F36A F 0.5643(14) -0.3917(15) 0.2002(11) 0.104(6) Uani 0.56 1 d PD A 1 F34B F 0.525(3) -0.4730(14) 0.3659(15) 0.098(10) Uani 0.44 1 d PD A 2 F35B F 0.5545(10) -0.3965(14) 0.1977(9) 0.040(3) Uani 0.44 1 d PD A 2 F36B F 0.3864(11) -0.3255(19) 0.290(2) 0.131(9) Uani 0.44 1 d PD A 2 O41 O -0.0533(2) 0.5644(2) 0.1420(2) 0.0355(6) Uani 1 1 d . . . C42 C 0.0115(3) 0.5761(3) 0.1979(3) 0.0321(9) Uani 1 1 d . . . C43 C 0.1334(3) 0.5569(3) 0.1773(3) 0.0346(10) Uani 1 1 d . . . H43A H 0.1707 0.5696 0.2273 0.042 Uiso 1 1 calc R . . C44 C 0.2029(3) 0.5197(3) 0.0862(3) 0.0289(9) Uani 1 1 d . . . O45 O 0.1709(2) 0.4994(2) 0.0113(2) 0.0307(6) Uani 1 1 d . . . C46 C -0.0556(4) 0.6156(4) 0.3007(4) 0.0493(12) Uani 1 1 d . . . C47 C 0.3378(3) 0.4950(3) 0.0760(3) 0.0316(9) Uani 1 1 d . . . F41 F -0.1358(3) 0.7193(3) 0.2697(3) 0.0842(10) Uani 1 1 d . . . F42 F 0.0122(2) 0.6257(3) 0.3617(2) 0.0776(9) Uani 1 1 d . . . F43 F -0.1140(3) 0.5418(3) 0.3683(2) 0.0778(9) Uani 1 1 d . . . F44 F 0.3810(2) 0.5359(2) -0.0292(2) 0.0612(7) Uani 1 1 d . . . F45 F 0.39173(19) 0.3805(2) 0.1082(2) 0.0579(7) Uani 1 1 d . . . F46 F 0.3687(2) 0.5419(2) 0.1372(2) 0.0593(7) 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 Mn1 0.0297(3) 0.0264(3) 0.0299(4) -0.0054(2) -0.0069(3) -0.0069(2) Mn2 0.0234(4) 0.0348(5) 0.0280(5) -0.0095(4) -0.0091(4) -0.0055(3) S1 0.0305(5) 0.0353(5) 0.0262(6) -0.0055(4) -0.0066(4) -0.0020(4) S2 0.0315(5) 0.0359(5) 0.0260(6) -0.0067(4) -0.0049(4) -0.0012(4) N1 0.0290(18) 0.0312(17) 0.0201(18) -0.0066(13) -0.0007(14) -0.0076(13) C1 0.028(2) 0.0248(19) 0.031(2) -0.0081(16) -0.0076(18) -0.0073(16) C2 0.028(2) 0.025(2) 0.032(2) -0.0067(17) -0.0060(18) -0.0081(17) O1 0.0317(15) 0.0347(14) 0.0263(16) -0.0033(12) -0.0072(13) -0.0042(12) C3 0.032(2) 0.029(2) 0.027(2) -0.0083(16) -0.0053(18) -0.0110(16) C4 0.034(2) 0.034(2) 0.028(2) -0.0065(17) -0.0057(19) -0.0093(17) C5 0.041(2) 0.043(2) 0.030(3) -0.0132(19) 0.002(2) -0.0183(19) C11 0.050(3) 0.058(3) 0.032(3) -0.009(2) 0.005(2) -0.019(2) C6 0.033(2) 0.043(2) 0.030(3) -0.0162(19) 0.0007(19) -0.0164(18) C12 0.035(2) 0.061(3) 0.050(3) -0.029(2) -0.001(2) -0.012(2) C7 0.025(2) 0.038(2) 0.037(3) -0.0125(18) -0.0062(19) -0.0111(17) C8 0.029(2) 0.033(2) 0.028(2) -0.0101(17) -0.0035(18) -0.0145(16) C9 0.030(2) 0.029(2) 0.031(2) -0.0089(17) -0.0060(19) -0.0106(17) O2 0.0268(14) 0.0362(15) 0.0344(17) -0.0049(12) -0.0068(13) -0.0056(12) C10 0.030(2) 0.029(2) 0.023(2) -0.0072(16) -0.0064(17) -0.0066(16) O21 0.0454(17) 0.0337(14) 0.0318(16) -0.0088(12) -0.0060(13) -0.0156(13) C22 0.037(2) 0.029(2) 0.037(3) -0.0011(18) -0.018(2) -0.0086(18) C23 0.040(2) 0.040(2) 0.038(3) -0.0032(19) -0.007(2) -0.0175(19) C24 0.031(2) 0.039(2) 0.033(3) -0.0042(19) -0.0058(19) -0.0087(18) O25 0.0355(15) 0.0366(15) 0.0384(17) -0.0119(13) -0.0016(13) -0.0113(12) C26 0.051(3) 0.037(2) 0.040(3) -0.001(2) -0.022(2) -0.015(2) C27 0.049(3) 0.061(3) 0.046(3) -0.017(2) 0.008(3) -0.026(3) F21 0.127(3) 0.0573(17) 0.0453(18) -0.0006(13) -0.0427(18) -0.0431(16) F22 0.0540(16) 0.0444(14) 0.075(2) -0.0273(13) -0.0072(14) -0.0145(12) F23 0.0590(16) 0.0532(15) 0.0679(19) -0.0120(13) -0.0173(14) -0.0310(13) F24 0.108(2) 0.099(2) 0.060(2) -0.0310(17) 0.0353(18) -0.072(2) F25 0.0713(19) 0.093(2) 0.0399(17) -0.0225(15) -0.0028(15) -0.0306(16) F26 0.0510(17) 0.088(2) 0.073(2) -0.0378(17) 0.0152(15) -0.0084(15) O31 0.0363(15) 0.0284(14) 0.0318(16) -0.0052(12) -0.0103(13) -0.0091(11) C32 0.026(2) 0.035(2) 0.026(2) -0.0077(17) -0.0013(17) -0.0083(17) C33 0.046(2) 0.035(2) 0.026(2) -0.0030(17) -0.006(2) -0.0201(18) C34 0.032(2) 0.038(2) 0.029(3) -0.0119(19) -0.0006(19) -0.0165(17) O35 0.0390(15) 0.0296(14) 0.0255(16) -0.0044(12) -0.0086(12) -0.0108(11) C36 0.048(3) 0.040(2) 0.031(3) -0.0052(19) -0.010(2) -0.018(2) C37 0.070(4) 0.051(3) 0.028(3) -0.006(2) -0.002(3) -0.037(3) F31 0.093(2) 0.0432(14) 0.0508(17) 0.0136(12) -0.0378(15) -0.0363(14) F32 0.0598(16) 0.0706(17) 0.0286(15) -0.0188(12) -0.0016(12) -0.0250(13) F33 0.0394(14) 0.0523(14) 0.0429(16) -0.0106(11) -0.0154(12) -0.0094(11) F34A 0.062(7) 0.080(5) 0.098(7) -0.022(5) -0.042(6) -0.030(5) F35A 0.158(12) 0.102(9) 0.038(6) 0.026(5) -0.031(5) -0.112(8) F36A 0.189(13) 0.106(9) 0.076(10) -0.056(8) 0.028(8) -0.111(9) F34B 0.21(3) 0.069(8) 0.061(10) -0.009(7) -0.047(10) -0.089(9) F35B 0.045(5) 0.056(7) 0.034(8) -0.024(5) 0.004(5) -0.026(4) F36B 0.049(8) 0.21(2) 0.23(2) -0.176(18) 0.064(10) -0.080(10) O41 0.0285(15) 0.0484(16) 0.0336(17) -0.0173(13) -0.0064(13) -0.0096(12) C42 0.032(2) 0.034(2) 0.032(2) -0.0114(18) -0.0070(19) -0.0070(17) C43 0.035(2) 0.048(2) 0.028(2) -0.0164(19) -0.0104(19) -0.0109(18) C44 0.029(2) 0.027(2) 0.027(2) -0.0026(17) -0.0064(18) -0.0079(16) O45 0.0252(14) 0.0422(15) 0.0278(16) -0.0131(12) -0.0067(12) -0.0089(11) C46 0.039(3) 0.072(3) 0.046(3) -0.030(3) -0.009(2) -0.013(2) C47 0.030(2) 0.039(2) 0.028(3) -0.0097(18) -0.0072(19) -0.0115(18) F41 0.073(2) 0.086(2) 0.078(2) -0.0532(18) -0.0099(17) 0.0217(17) F42 0.0538(17) 0.145(3) 0.067(2) -0.074(2) 0.0021(15) -0.0315(17) F43 0.082(2) 0.120(2) 0.055(2) -0.0495(18) 0.0270(17) -0.057(2) F44 0.0338(14) 0.102(2) 0.0368(17) 0.0020(14) -0.0064(12) -0.0280(13) F45 0.0301(13) 0.0493(15) 0.087(2) -0.0116(13) -0.0209(14) -0.0033(11) F46 0.0358(14) 0.096(2) 0.073(2) -0.0520(16) -0.0042(13) -0.0252(13) _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 Mn1 O21 2.112(2) . ? Mn1 O31 2.120(3) . ? Mn1 O35 2.128(2) . ? Mn1 O25 2.131(3) . ? Mn1 O1 2.298(3) . ? Mn1 N1 2.329(3) . ? Mn2 O45 2.117(2) 2_565 ? Mn2 O45 2.117(2) . ? Mn2 O41 2.125(3) . ? Mn2 O41 2.125(3) 2_565 ? Mn2 O2 2.204(3) 2_565 ? Mn2 O2 2.204(3) . ? S1 C10 1.727(4) . ? S1 S2 2.0708(15) . ? S2 N1 1.648(3) . ? N1 C1 1.322(4) . ? C1 C10 1.396(5) . ? C1 C2 1.498(5) . ? C2 O1 1.225(4) . ? C2 C3 1.464(5) . ? C3 C4 1.383(5) . ? C3 C8 1.417(5) . ? C4 C5 1.394(5) . ? C4 H4A 0.9500 . ? C5 C6 1.415(6) . ? C5 C11 1.505(6) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C6 C7 1.387(5) . ? C6 C12 1.505(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C7 C8 1.386(5) . ? C7 H7A 0.9500 . ? C8 C9 1.479(5) . ? C9 O2 1.253(4) . ? C9 C10 1.435(5) . ? O21 C22 1.254(4) . ? C22 C23 1.390(6) . ? C22 C26 1.530(5) . ? C23 C24 1.392(5) . ? C23 H23A 0.9500 . ? C24 O25 1.256(4) . ? C24 C27 1.522(6) . ? C26 F22 1.323(5) . ? C26 F21 1.330(5) . ? C26 F23 1.336(5) . ? C27 F24 1.331(5) . ? C27 F26 1.332(5) . ? C27 F25 1.336(5) . ? O31 C32 1.243(4) . ? C32 C33 1.394(5) . ? C32 C36 1.541(5) . ? C33 C34 1.379(5) . ? C33 H33A 0.9500 . ? C34 O35 1.264(4) . ? C34 C37 1.532(5) . ? C36 F31 1.330(4) . ? C36 F32 1.334(5) . ? C36 F33 1.337(5) . ? C37 F36A 1.299(10) . ? C37 F35A 1.301(10) . ? C37 F36B 1.305(12) . ? C37 F34A 1.320(9) . ? C37 F35B 1.322(10) . ? C37 F34B 1.342(13) . ? O41 C42 1.255(4) . ? C42 C43 1.392(5) . ? C42 C46 1.525(6) . ? C43 C44 1.394(5) . ? C43 H43A 0.9500 . ? C44 O45 1.247(4) . ? C44 C47 1.541(5) . ? C46 F41 1.319(5) . ? C46 F42 1.325(5) . ? C46 F43 1.327(5) . ? C47 F46 1.316(4) . ? C47 F45 1.319(4) . ? C47 F44 1.320(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O21 Mn1 O31 90.17(10) . . ? O21 Mn1 O35 172.91(10) . . ? O31 Mn1 O35 84.75(9) . . ? O21 Mn1 O25 83.45(10) . . ? O31 Mn1 O25 115.32(10) . . ? O35 Mn1 O25 94.24(10) . . ? O21 Mn1 O1 94.41(10) . . ? O31 Mn1 O1 90.45(10) . . ? O35 Mn1 O1 90.58(10) . . ? O25 Mn1 O1 154.09(10) . . ? O21 Mn1 N1 93.78(10) . . ? O31 Mn1 N1 161.28(10) . . ? O35 Mn1 N1 92.61(10) . . ? O25 Mn1 N1 83.32(10) . . ? O1 Mn1 N1 71.02(10) . . ? O45 Mn2 O45 180.0 2_565 . ? O45 Mn2 O41 95.27(10) 2_565 . ? O45 Mn2 O41 84.73(10) . . ? O45 Mn2 O41 84.73(10) 2_565 2_565 ? O45 Mn2 O41 95.27(10) . 2_565 ? O41 Mn2 O41 180.0 . 2_565 ? O45 Mn2 O2 88.15(10) 2_565 2_565 ? O45 Mn2 O2 91.85(10) . 2_565 ? O41 Mn2 O2 92.23(10) . 2_565 ? O41 Mn2 O2 87.77(10) 2_565 2_565 ? O45 Mn2 O2 91.85(10) 2_565 . ? O45 Mn2 O2 88.15(10) . . ? O41 Mn2 O2 87.77(10) . . ? O41 Mn2 O2 92.23(10) 2_565 . ? O2 Mn2 O2 180.0 2_565 . ? C10 S1 S2 91.59(13) . . ? N1 S2 S1 98.43(12) . . ? C1 N1 S2 114.4(3) . . ? C1 N1 Mn1 114.5(2) . . ? S2 N1 Mn1 131.07(16) . . ? N1 C1 C10 120.7(3) . . ? N1 C1 C2 117.3(3) . . ? C10 C1 C2 122.0(3) . . ? O1 C2 C3 125.3(4) . . ? O1 C2 C1 118.4(3) . . ? C3 C2 C1 116.3(3) . . ? C2 O1 Mn1 118.6(2) . . ? C4 C3 C8 120.2(3) . . ? C4 C3 C2 119.3(3) . . ? C8 C3 C2 120.5(3) . . ? C3 C4 C5 121.4(4) . . ? C3 C4 H4A 119.3 . . ? C5 C4 H4A 119.3 . . ? C4 C5 C6 118.8(4) . . ? C4 C5 C11 120.2(4) . . ? C6 C5 C11 121.0(4) . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C6 C5 119.1(4) . . ? C7 C6 C12 120.5(4) . . ? C5 C6 C12 120.4(4) . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C7 C6 122.6(4) . . ? C8 C7 H7A 118.7 . . ? C6 C7 H7A 118.7 . . ? C7 C8 C3 117.8(4) . . ? C7 C8 C9 120.0(3) . . ? C3 C8 C9 122.2(3) . . ? O2 C9 C10 121.4(3) . . ? O2 C9 C8 121.4(3) . . ? C10 C9 C8 117.1(3) . . ? C9 O2 Mn2 139.0(2) . . ? C1 C10 C9 121.8(3) . . ? C1 C10 S1 114.8(3) . . ? C9 C10 S1 123.4(3) . . ? C22 O21 Mn1 129.4(3) . . ? O21 C22 C23 127.8(4) . . ? O21 C22 C26 112.8(4) . . ? C23 C22 C26 119.3(4) . . ? C22 C23 C24 122.3(4) . . ? C22 C23 H23A 118.9 . . ? C24 C23 H23A 118.9 . . ? O25 C24 C23 127.6(4) . . ? O25 C24 C27 113.4(4) . . ? C23 C24 C27 118.9(4) . . ? C24 O25 Mn1 128.8(3) . . ? F22 C26 F21 108.0(4) . . ? F22 C26 F23 107.5(3) . . ? F21 C26 F23 106.3(3) . . ? F22 C26 C22 111.2(3) . . ? F21 C26 C22 110.1(3) . . ? F23 C26 C22 113.4(4) . . ? F24 C27 F26 106.9(4) . . ? F24 C27 F25 106.8(4) . . ? F26 C27 F25 105.6(4) . . ? F24 C27 C24 114.3(4) . . ? F26 C27 C24 111.5(4) . . ? F25 C27 C24 111.2(4) . . ? C32 O31 Mn1 126.7(2) . . ? O31 C32 C33 128.2(4) . . ? O31 C32 C36 114.1(3) . . ? C33 C32 C36 117.7(3) . . ? C34 C33 C32 122.9(4) . . ? C34 C33 H33A 118.6 . . ? C32 C33 H33A 118.6 . . ? O35 C34 C33 128.3(3) . . ? O35 C34 C37 113.1(3) . . ? C33 C34 C37 118.5(3) . . ? C34 O35 Mn1 125.2(2) . . ? F31 C36 F32 107.5(3) . . ? F31 C36 F33 107.4(3) . . ? F32 C36 F33 107.1(3) . . ? F31 C36 C32 113.2(3) . . ? F32 C36 C32 111.0(3) . . ? F33 C36 C32 110.4(3) . . ? F36A C37 F35A 112.0(13) . . ? F36A C37 F36B 117.3(13) . . ? F35A C37 F36B 89.2(16) . . ? F36A C37 F34A 103.0(11) . . ? F35A C37 F34A 106.9(14) . . ? F36B C37 F34A 19.0(15) . . ? F36A C37 F35B 7.2(14) . . ? F35A C37 F35B 108.9(13) . . ? F36B C37 F35B 111.4(13) . . ? F34A C37 F35B 98.3(9) . . ? F36A C37 F34B 101.0(15) . . ? F35A C37 F34B 18(3) . . ? F36B C37 F34B 106.9(18) . . ? F34A C37 F34B 124.2(16) . . ? F35B C37 F34B 99.7(13) . . ? F36A C37 C34 108.2(8) . . ? F35A C37 C34 116.3(9) . . ? F36B C37 C34 113.1(10) . . ? F34A C37 C34 109.6(8) . . ? F35B C37 C34 115.1(8) . . ? F34B C37 C34 109.4(10) . . ? C42 O41 Mn2 127.7(2) . . ? O41 C42 C43 128.2(4) . . ? O41 C42 C46 113.7(3) . . ? C43 C42 C46 118.1(4) . . ? C42 C43 C44 122.5(4) . . ? C42 C43 H43A 118.7 . . ? C44 C43 H43A 118.7 . . ? O45 C44 C43 128.4(3) . . ? O45 C44 C47 113.9(3) . . ? C43 C44 C47 117.6(3) . . ? C44 O45 Mn2 128.0(2) . . ? F41 C46 F42 107.0(4) . . ? F41 C46 F43 106.5(4) . . ? F42 C46 F43 107.2(4) . . ? F41 C46 C42 110.1(4) . . ? F42 C46 C42 114.3(4) . . ? F43 C46 C42 111.4(4) . . ? F46 C47 F45 107.2(3) . . ? F46 C47 F44 107.6(3) . . ? F45 C47 F44 107.2(3) . . ? F46 C47 C44 113.6(3) . . ? F45 C47 C44 110.4(3) . . ? F44 C47 C44 110.7(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 S1 S2 N1 1.41(16) . . . . ? S1 S2 N1 C1 -0.6(3) . . . . ? S1 S2 N1 Mn1 -178.73(16) . . . . ? O21 Mn1 N1 C1 -89.3(2) . . . . ? O31 Mn1 N1 C1 12.5(5) . . . . ? O35 Mn1 N1 C1 93.8(2) . . . . ? O25 Mn1 N1 C1 -172.2(2) . . . . ? O1 Mn1 N1 C1 4.1(2) . . . . ? O21 Mn1 N1 S2 88.9(2) . . . . ? O31 Mn1 N1 S2 -169.4(2) . . . . ? O35 Mn1 N1 S2 -88.1(2) . . . . ? O25 Mn1 N1 S2 5.9(2) . . . . ? O1 Mn1 N1 S2 -177.8(2) . . . . ? S2 N1 C1 C10 -0.8(4) . . . . ? Mn1 N1 C1 C10 177.6(3) . . . . ? S2 N1 C1 C2 178.0(2) . . . . ? Mn1 N1 C1 C2 -3.5(4) . . . . ? N1 C1 C2 O1 -0.6(5) . . . . ? C10 C1 C2 O1 178.3(3) . . . . ? N1 C1 C2 C3 178.9(3) . . . . ? C10 C1 C2 C3 -2.2(5) . . . . ? C3 C2 O1 Mn1 -174.9(3) . . . . ? C1 C2 O1 Mn1 4.6(4) . . . . ? O21 Mn1 O1 C2 87.8(3) . . . . ? O31 Mn1 O1 C2 178.0(3) . . . . ? O35 Mn1 O1 C2 -97.3(3) . . . . ? O25 Mn1 O1 C2 3.7(4) . . . . ? N1 Mn1 O1 C2 -4.7(2) . . . . ? O1 C2 C3 C4 1.1(6) . . . . ? C1 C2 C3 C4 -178.3(3) . . . . ? O1 C2 C3 C8 178.2(3) . . . . ? C1 C2 C3 C8 -1.3(5) . . . . ? C8 C3 C4 C5 -0.3(5) . . . . ? C2 C3 C4 C5 176.8(3) . . . . ? C3 C4 C5 C6 -1.2(6) . . . . ? C3 C4 C5 C11 179.7(4) . . . . ? C4 C5 C6 C7 1.3(5) . . . . ? C11 C5 C6 C7 -179.5(3) . . . . ? C4 C5 C6 C12 -177.6(3) . . . . ? C11 C5 C6 C12 1.6(6) . . . . ? C5 C6 C7 C8 0.1(6) . . . . ? C12 C6 C7 C8 178.9(3) . . . . ? C6 C7 C8 C3 -1.5(5) . . . . ? C6 C7 C8 C9 179.5(3) . . . . ? C4 C3 C8 C7 1.6(5) . . . . ? C2 C3 C8 C7 -175.4(3) . . . . ? C4 C3 C8 C9 -179.5(3) . . . . ? C2 C3 C8 C9 3.5(5) . . . . ? C7 C8 C9 O2 -4.0(5) . . . . ? C3 C8 C9 O2 177.1(3) . . . . ? C7 C8 C9 C10 176.7(3) . . . . ? C3 C8 C9 C10 -2.2(5) . . . . ? C10 C9 O2 Mn2 -59.7(5) . . . . ? C8 C9 O2 Mn2 121.1(3) . . . . ? O45 Mn2 O2 C9 -176.3(4) 2_565 . . . ? O45 Mn2 O2 C9 3.7(4) . . . . ? O41 Mn2 O2 C9 -81.1(4) . . . . ? O41 Mn2 O2 C9 98.9(4) 2_565 . . . ? O2 Mn2 O2 C9 -52(9) 2_565 . . . ? N1 C1 C10 C9 -177.6(3) . . . . ? C2 C1 C10 C9 3.6(5) . . . . ? N1 C1 C10 S1 2.2(4) . . . . ? C2 C1 C10 S1 -176.6(3) . . . . ? O2 C9 C10 C1 179.4(3) . . . . ? C8 C9 C10 C1 -1.4(5) . . . . ? O2 C9 C10 S1 -0.4(5) . . . . ? C8 C9 C10 S1 178.9(3) . . . . ? S2 S1 C10 C1 -2.0(3) . . . . ? S2 S1 C10 C9 177.8(3) . . . . ? O31 Mn1 O21 C22 121.7(3) . . . . ? O35 Mn1 O21 C22 77.6(9) . . . . ? O25 Mn1 O21 C22 6.3(3) . . . . ? O1 Mn1 O21 C22 -147.8(3) . . . . ? N1 Mn1 O21 C22 -76.6(3) . . . . ? Mn1 O21 C22 C23 -3.3(6) . . . . ? Mn1 O21 C22 C26 176.2(2) . . . . ? O21 C22 C23 C24 -1.3(6) . . . . ? C26 C22 C23 C24 179.2(4) . . . . ? C22 C23 C24 O25 -0.8(6) . . . . ? C22 C23 C24 C27 178.4(4) . . . . ? C23 C24 O25 Mn1 7.2(6) . . . . ? C27 C24 O25 Mn1 -172.0(3) . . . . ? O21 Mn1 O25 C24 -8.1(3) . . . . ? O31 Mn1 O25 C24 -95.1(3) . . . . ? O35 Mn1 O25 C24 178.7(3) . . . . ? O1 Mn1 O25 C24 78.5(4) . . . . ? N1 Mn1 O25 C24 86.5(3) . . . . ? O21 C22 C26 F22 -67.4(4) . . . . ? C23 C22 C26 F22 112.1(4) . . . . ? O21 C22 C26 F21 52.2(5) . . . . ? C23 C22 C26 F21 -128.2(4) . . . . ? O21 C22 C26 F23 171.2(3) . . . . ? C23 C22 C26 F23 -9.2(5) . . . . ? O25 C24 C27 F24 177.5(4) . . . . ? C23 C24 C27 F24 -1.8(6) . . . . ? O25 C24 C27 F26 -61.1(5) . . . . ? C23 C24 C27 F26 119.6(4) . . . . ? O25 C24 C27 F25 56.5(5) . . . . ? C23 C24 C27 F25 -122.8(4) . . . . ? O21 Mn1 O31 C32 168.3(3) . . . . ? O35 Mn1 O31 C32 -16.6(3) . . . . ? O25 Mn1 O31 C32 -108.8(3) . . . . ? O1 Mn1 O31 C32 73.9(3) . . . . ? N1 Mn1 O31 C32 66.0(4) . . . . ? Mn1 O31 C32 C33 7.6(5) . . . . ? Mn1 O31 C32 C36 -174.6(2) . . . . ? O31 C32 C33 C34 6.2(6) . . . . ? C36 C32 C33 C34 -171.6(4) . . . . ? C32 C33 C34 O35 -1.1(7) . . . . ? C32 C33 C34 C37 178.4(4) . . . . ? C33 C34 O35 Mn1 -16.4(6) . . . . ? C37 C34 O35 Mn1 164.1(2) . . . . ? O21 Mn1 O35 C34 64.8(9) . . . . ? O31 Mn1 O35 C34 20.5(3) . . . . ? O25 Mn1 O35 C34 135.6(3) . . . . ? O1 Mn1 O35 C34 -69.9(3) . . . . ? N1 Mn1 O35 C34 -140.9(3) . . . . ? O31 C32 C36 F31 -177.9(3) . . . . ? C33 C32 C36 F31 0.1(5) . . . . ? O31 C32 C36 F32 61.1(4) . . . . ? C33 C32 C36 F32 -120.8(4) . . . . ? O31 C32 C36 F33 -57.5(4) . . . . ? C33 C32 C36 F33 120.6(4) . . . . ? O35 C34 C37 F36A 57.8(9) . . . . ? C33 C34 C37 F36A -121.8(9) . . . . ? O35 C34 C37 F35A -175.2(15) . . . . ? C33 C34 C37 F35A 5.3(15) . . . . ? O35 C34 C37 F36B -73.9(12) . . . . ? C33 C34 C37 F36B 106.5(12) . . . . ? O35 C34 C37 F34A -53.8(8) . . . . ? C33 C34 C37 F34A 126.6(8) . . . . ? O35 C34 C37 F35B 55.8(8) . . . . ? C33 C34 C37 F35B -123.8(7) . . . . ? O35 C34 C37 F34B 167.0(16) . . . . ? C33 C34 C37 F34B -12.6(16) . . . . ? O45 Mn2 O41 C42 173.9(3) 2_565 . . . ? O45 Mn2 O41 C42 -6.1(3) . . . . ? O41 Mn2 O41 C42 167(4) 2_565 . . . ? O2 Mn2 O41 C42 -97.7(3) 2_565 . . . ? O2 Mn2 O41 C42 82.3(3) . . . . ? Mn2 O41 C42 C43 4.4(6) . . . . ? Mn2 O41 C42 C46 -175.2(3) . . . . ? O41 C42 C43 C44 -0.2(6) . . . . ? C46 C42 C43 C44 179.4(4) . . . . ? C42 C43 C44 O45 0.7(6) . . . . ? C42 C43 C44 C47 -176.7(3) . . . . ? C43 C44 O45 Mn2 -5.5(5) . . . . ? C47 C44 O45 Mn2 172.1(2) . . . . ? O45 Mn2 O45 C44 -123.1(16) 2_565 . . . ? O41 Mn2 O45 C44 6.6(3) . . . . ? O41 Mn2 O45 C44 -173.4(3) 2_565 . . . ? O2 Mn2 O45 C44 98.6(3) 2_565 . . . ? O2 Mn2 O45 C44 -81.4(3) . . . . ? O41 C42 C46 F41 -61.0(5) . . . . ? C43 C42 C46 F41 119.4(4) . . . . ? O41 C42 C46 F42 178.6(4) . . . . ? C43 C42 C46 F42 -1.0(6) . . . . ? O41 C42 C46 F43 56.9(5) . . . . ? C43 C42 C46 F43 -122.8(4) . . . . ? O45 C44 C47 F46 164.7(3) . . . . ? C43 C44 C47 F46 -17.4(5) . . . . ? O45 C44 C47 F45 -74.9(4) . . . . ? C43 C44 C47 F45 102.9(4) . . . . ? O45 C44 C47 F44 43.6(4) . . . . ? C43 C44 C47 F44 -138.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.338 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.075 # Attachment '- DaveNH2Br_precursor_mj.cif' data_two _database_code_depnum_ccdc_archive 'CCDC 896031' #TrackingRef '- DaveNH2Br_precursor_mj.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-amino-3-bromo-6,7-dimethylnapthalene-1,4-dione ; _chemical_name_common 2-amino-3-bromo-6,7-dimethylnapthalene-1,4-dione _chemical_melting_point 226-228 _chemical_formula_moiety 'C12 H10 Br N O2,0.5(H2O)' _chemical_formula_sum 'C12 H11 Br N O2.5' _chemical_formula_weight 289.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/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 7.72070(7) _cell_length_b 13.73969(16) _cell_length_c 21.1400(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.0880(10) _cell_angle_gamma 90.00 _cell_volume 2236.83(4) _cell_formula_units_Z 8 _cell_measurement_temperature 149.9 _cell_measurement_reflns_used 11776 _cell_measurement_theta_min 4.1898 _cell_measurement_theta_max 76.5308 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.717 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 4.942 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.48298 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details Abspack _exptl_special_details ; ? ; _diffrn_ambient_temperature 149.9 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3693 _diffrn_reflns_number 18184 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 76.73 _reflns_number_total 2345 _reflns_number_gt 2338 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0288P)^2^+8.3145P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2345 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0329 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0817 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_restrained_S_all 1.160 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.24500(4) 0.39299(2) 0.728544(12) 0.03003(11) Uani 1 1 d . . . O1 O 0.3510(3) 0.56393(16) 0.51760(10) 0.0406(5) Uani 1 1 d . . . N1 N 0.3941(3) 0.55329(17) 0.64328(12) 0.0325(5) Uani 1 1 d . . . H1A H 0.4111 0.5513 0.6849 0.039 Uiso 1 1 calc R . . H1B H 0.4400 0.6005 0.6219 0.039 Uiso 1 1 calc R . . C1 C 0.2822(3) 0.49447(19) 0.54108(13) 0.0257(5) Uani 1 1 d . . . O2 O 0.0584(2) 0.26133(14) 0.62958(8) 0.0262(4) Uani 1 1 d . . . C2 C 0.2972(3) 0.48367(19) 0.61223(12) 0.0242(5) Uani 1 1 d . . . O3 O 0.0000 0.1707(2) 0.7500 0.0371(7) Uani 1 2 d SG . . H3A H 0.0730 0.2021 0.7309 0.056 Uiso 0.50 1 d PG . . H3B H -0.0240 0.2013 0.7830 0.056 Uiso 0.50 1 d PG . . C3 C 0.2191(3) 0.40686(19) 0.63957(12) 0.0222(5) Uani 1 1 d . . . C4 C 0.1217(3) 0.33199(18) 0.60381(11) 0.0209(5) Uani 1 1 d . . . C5 C 0.0048(3) 0.27739(18) 0.49644(12) 0.0227(5) Uani 1 1 d . . . H5 H -0.0508 0.2253 0.5165 0.027 Uiso 1 1 calc R . . C6 C -0.0131(3) 0.28558(19) 0.43020(12) 0.0229(5) Uani 1 1 d . . . C7 C 0.0699(3) 0.3622(2) 0.40049(12) 0.0250(5) Uani 1 1 d . . . C8 C 0.1661(4) 0.42904(19) 0.43787(12) 0.0253(5) Uani 1 1 d . . . H8 H 0.2218 0.4813 0.4181 0.030 Uiso 1 1 calc R . . C9 C 0.1823(3) 0.42091(18) 0.50349(12) 0.0227(5) Uani 1 1 d . . . C10 C 0.1022(3) 0.34389(18) 0.53331(11) 0.0202(5) Uani 1 1 d . . . C11 C -0.1224(4) 0.2130(2) 0.39169(13) 0.0292(6) Uani 1 1 d . . . H11A H -0.1648 0.1631 0.4199 0.044 Uiso 1 1 calc R . . H11B H -0.0521 0.1823 0.3604 0.044 Uiso 1 1 calc R . . H11C H -0.2214 0.2465 0.3697 0.044 Uiso 1 1 calc R . . C12 C 0.0571(4) 0.3721(2) 0.32932(13) 0.0324(6) Uani 1 1 d . . . H12A H 0.1144 0.4324 0.3175 0.049 Uiso 1 1 calc R . . H12B H -0.0654 0.3741 0.3136 0.049 Uiso 1 1 calc R . . H12C H 0.1139 0.3164 0.3106 0.049 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 Br1 0.03435(18) 0.03579(18) 0.01960(15) -0.00103(10) -0.00054(11) -0.00140(11) O1 0.0621(15) 0.0290(11) 0.0309(11) 0.0002(9) 0.0057(10) -0.0201(10) N1 0.0369(13) 0.0214(11) 0.0402(13) -0.0029(10) 0.0101(11) -0.0090(10) C1 0.0296(13) 0.0218(12) 0.0257(13) -0.0009(10) 0.0039(10) -0.0018(10) O2 0.0303(9) 0.0269(9) 0.0215(9) 0.0042(7) 0.0016(7) -0.0049(8) C2 0.0247(12) 0.0237(13) 0.0239(12) -0.0031(10) 0.0002(9) 0.0010(10) O3 0.063(2) 0.0264(14) 0.0223(14) 0.000 0.0078(13) 0.000 C3 0.0237(12) 0.0256(13) 0.0170(11) -0.0022(9) 0.0003(9) 0.0020(10) C4 0.0180(11) 0.0242(12) 0.0207(12) 0.0000(9) 0.0024(9) 0.0023(9) C5 0.0241(12) 0.0212(12) 0.0227(12) 0.0007(10) 0.0011(9) -0.0008(10) C6 0.0230(12) 0.0235(12) 0.0222(12) -0.0019(10) 0.0006(9) 0.0022(10) C7 0.0289(13) 0.0253(13) 0.0208(12) 0.0013(10) 0.0026(10) 0.0043(10) C8 0.0305(13) 0.0225(12) 0.0233(12) 0.0030(10) 0.0050(10) -0.0013(10) C9 0.0251(12) 0.0194(12) 0.0235(12) 0.0014(9) 0.0022(9) 0.0004(10) C10 0.0221(11) 0.0192(11) 0.0193(11) 0.0023(9) 0.0015(9) 0.0023(9) C11 0.0302(13) 0.0327(14) 0.0240(13) -0.0044(11) -0.0022(10) -0.0044(11) C12 0.0418(16) 0.0351(15) 0.0204(13) 0.0016(11) 0.0029(11) 0.0014(12) _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 Br1 C3 1.887(2) . ? O1 C1 1.215(3) . ? N1 C2 1.355(3) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? C1 C9 1.470(4) . ? C1 C2 1.508(4) . ? O2 C4 1.231(3) . ? C2 C3 1.364(4) . ? O3 H3A 0.8372 . ? O3 H3B 0.8471 . ? C3 C4 1.454(4) . ? C4 C10 1.496(3) . ? C5 C10 1.387(4) . ? C5 C6 1.402(4) . ? C5 H5 0.9500 . ? C6 C7 1.404(4) . ? C6 C11 1.507(4) . ? C7 C8 1.391(4) . ? C7 C12 1.507(4) . ? C8 C9 1.388(4) . ? C8 H8 0.9500 . ? C9 C10 1.398(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 N1 H1A 120.0 . . ? C2 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? O1 C1 C9 123.2(2) . . ? O1 C1 C2 118.7(2) . . ? C9 C1 C2 118.2(2) . . ? N1 C2 C3 125.9(2) . . ? N1 C2 C1 114.5(2) . . ? C3 C2 C1 119.6(2) . . ? H3A O3 H3B 109.6 . . ? C2 C3 C4 123.7(2) . . ? C2 C3 Br1 118.80(19) . . ? C4 C3 Br1 117.45(18) . . ? O2 C4 C3 122.3(2) . . ? O2 C4 C10 120.8(2) . . ? C3 C4 C10 116.9(2) . . ? C10 C5 C6 121.3(2) . . ? C10 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C7 119.4(2) . . ? C5 C6 C11 119.9(2) . . ? C7 C6 C11 120.7(2) . . ? C8 C7 C6 118.9(2) . . ? C8 C7 C12 120.1(2) . . ? C6 C7 C12 121.0(2) . . ? C9 C8 C7 121.4(2) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 120.0(2) . . ? C8 C9 C1 119.4(2) . . ? C10 C9 C1 120.6(2) . . ? C5 C10 C9 119.0(2) . . ? C5 C10 C4 120.0(2) . . ? C9 C10 C4 121.0(2) . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 76.73 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.929 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.072 # Attachment '- DaveRad_kplabels_mj.cif' data_k11111 _database_code_depnum_ccdc_archive 'CCDC 896032' #TrackingRef '- DaveRad_kplabels_mj.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N O2 S2' _chemical_formula_sum 'C12 H8 N O2 S2' _chemical_formula_weight 262.31 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.055(2) _cell_length_b 7.9789(16) _cell_length_c 13.222(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.03(3) _cell_angle_gamma 90.00 _cell_volume 1073.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 23218 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.481 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.785 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 8545 _diffrn_reflns_av_R_equivalents 0.0738 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1893 _reflns_number_gt 1500 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0498P)^2^+0.8433P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1893 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1130 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 S1 S 0.56925(7) 0.55223(9) 0.14150(6) 0.0258(2) Uani 1 1 d . . . N1 N 0.5322(2) 0.2095(3) 0.17778(19) 0.0261(6) Uani 1 1 d . . . C1 C 0.5981(3) 0.2268(3) 0.1153(2) 0.0243(6) Uani 1 1 d . . . O1 O 0.6312(2) -0.0648(2) 0.10497(18) 0.0375(6) Uani 1 1 d . . . S2 S 0.48758(7) 0.38433(9) 0.21742(6) 0.0271(2) Uani 1 1 d . . . O2 O 0.7398(2) 0.5648(2) 0.01125(17) 0.0310(5) Uani 1 1 d . . . C2 C 0.6502(3) 0.0753(3) 0.0773(2) 0.0256(7) Uani 1 1 d . . . C3 C 0.7233(3) 0.1077(3) 0.0066(2) 0.0240(6) Uani 1 1 d . . . C4 C 0.7675(3) -0.0297(4) -0.0359(2) 0.0259(7) Uani 1 1 d . . . H4A H 0.7495 -0.1401 -0.0188 0.031 Uiso 1 1 calc R . . C5 C 0.8370(3) -0.0075(4) -0.1024(2) 0.0264(7) Uani 1 1 d . . . C6 C 0.8640(3) 0.1570(4) -0.1272(2) 0.0291(7) Uani 1 1 d . . . C7 C 0.8194(3) 0.2922(4) -0.0849(2) 0.0269(7) Uani 1 1 d . . . H7A H 0.8372 0.4026 -0.1021 0.032 Uiso 1 1 calc R . . C8 C 0.7496(3) 0.2708(3) -0.0185(2) 0.0242(6) Uani 1 1 d . . . C9 C 0.7073(3) 0.4218(3) 0.0257(2) 0.0238(6) Uani 1 1 d . . . C10 C 0.6258(3) 0.3885(3) 0.0852(2) 0.0227(6) Uani 1 1 d . . . C11 C 0.8836(3) -0.1590(4) -0.1455(3) 0.0340(7) Uani 1 1 d . . . H11A H 0.8513 -0.2611 -0.1232 0.051 Uiso 1 1 calc R . . H11B H 0.9799 -0.1605 -0.1154 0.051 Uiso 1 1 calc R . . H11C H 0.8499 -0.1537 -0.2259 0.051 Uiso 1 1 calc R . . C12 C 0.9436(3) 0.1877(4) -0.1957(2) 0.0344(7) Uani 1 1 d . . . H12A H 0.9358 0.3057 -0.2180 0.052 Uiso 1 1 calc R . . H12B H 0.9106 0.1164 -0.2612 0.052 Uiso 1 1 calc R . . H12C H 1.0361 0.1610 -0.1524 0.052 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 S1 0.0332(4) 0.0214(4) 0.0260(4) -0.0009(3) 0.0152(3) 0.0007(3) N1 0.0315(14) 0.0254(13) 0.0235(13) -0.0005(10) 0.0130(11) 0.0015(11) C1 0.0278(16) 0.0248(15) 0.0188(15) -0.0003(12) 0.0075(13) 0.0010(12) O1 0.0589(15) 0.0223(11) 0.0469(14) 0.0015(10) 0.0374(12) 0.0010(10) S2 0.0365(5) 0.0240(4) 0.0261(4) 0.0007(3) 0.0180(3) 0.0022(3) O2 0.0397(12) 0.0231(11) 0.0371(13) 0.0012(9) 0.0226(10) -0.0019(9) C2 0.0295(16) 0.0241(15) 0.0247(16) -0.0001(12) 0.0122(13) 0.0010(12) C3 0.0233(15) 0.0255(15) 0.0203(14) 0.0007(12) 0.0054(12) 0.0018(12) C4 0.0262(15) 0.0255(16) 0.0251(16) -0.0010(12) 0.0092(13) -0.0002(12) C5 0.0242(15) 0.0322(16) 0.0215(15) -0.0002(13) 0.0074(13) 0.0021(13) C6 0.0252(16) 0.0394(17) 0.0219(15) 0.0013(13) 0.0084(13) 0.0019(13) C7 0.0287(16) 0.0310(15) 0.0216(15) 0.0053(12) 0.0107(13) 0.0004(13) C8 0.0273(16) 0.0242(15) 0.0203(15) 0.0015(12) 0.0084(13) 0.0019(12) C9 0.0256(15) 0.0223(15) 0.0218(15) 0.0013(12) 0.0076(13) 0.0003(12) C10 0.0245(15) 0.0206(14) 0.0195(14) 0.0009(11) 0.0050(12) 0.0013(11) C11 0.0377(18) 0.0379(18) 0.0303(17) -0.0061(14) 0.0175(15) 0.0016(15) C12 0.0339(18) 0.0409(18) 0.0309(17) 0.0033(15) 0.0153(15) 0.0038(14) _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 C10 1.737(3) . ? S1 S2 2.0800(11) . ? N1 C1 1.305(4) . ? N1 S2 1.633(2) . ? C1 C10 1.418(4) . ? C1 C2 1.507(4) . ? O1 C2 1.220(3) . ? O2 C9 1.234(3) . ? C2 C3 1.477(4) . ? C3 C8 1.402(4) . ? C3 C4 1.404(4) . ? C4 C5 1.387(4) . ? C4 H4A 0.9500 . ? C5 C6 1.412(4) . ? C5 C11 1.510(4) . ? C6 C7 1.391(4) . ? C6 C12 1.510(4) . ? C7 C8 1.388(4) . ? C7 H7A 0.9500 . ? C8 C9 1.492(4) . ? C9 C10 1.433(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 C10 S1 S2 91.10(10) . . ? C1 N1 S2 115.22(19) . . ? N1 C1 C10 120.6(2) . . ? N1 C1 C2 120.4(2) . . ? C10 C1 C2 118.9(2) . . ? N1 S2 S1 98.78(9) . . ? O1 C2 C3 123.4(2) . . ? O1 C2 C1 120.1(3) . . ? C3 C2 C1 116.5(2) . . ? C8 C3 C4 119.5(3) . . ? C8 C3 C2 121.8(2) . . ? C4 C3 C2 118.6(2) . . ? C5 C4 C3 121.4(3) . . ? C5 C4 H4A 119.3 . . ? C3 C4 H4A 119.3 . . ? C4 C5 C6 119.0(3) . . ? C4 C5 C11 119.5(3) . . ? C6 C5 C11 121.5(3) . . ? C7 C6 C5 119.2(3) . . ? C7 C6 C12 119.8(3) . . ? C5 C6 C12 121.0(3) . . ? C8 C7 C6 122.1(3) . . ? C8 C7 H7A 118.9 . . ? C6 C7 H7A 118.9 . . ? C7 C8 C3 118.8(3) . . ? C7 C8 C9 119.1(2) . . ? C3 C8 C9 122.1(3) . . ? O2 C9 C10 122.7(3) . . ? O2 C9 C8 122.1(3) . . ? C10 C9 C8 115.2(2) . . ? C1 C10 C9 125.0(2) . . ? C1 C10 S1 114.3(2) . . ? C9 C10 S1 120.3(2) . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 S2 N1 C1 C10 -0.5(4) . . . . ? S2 N1 C1 C2 177.3(2) . . . . ? C1 N1 S2 S1 -0.7(2) . . . . ? C10 S1 S2 N1 1.29(12) . . . . ? N1 C1 C2 O1 -0.1(4) . . . . ? C10 C1 C2 O1 177.7(3) . . . . ? N1 C1 C2 C3 179.9(2) . . . . ? C10 C1 C2 C3 -2.3(4) . . . . ? O1 C2 C3 C8 -176.3(3) . . . . ? C1 C2 C3 C8 3.7(4) . . . . ? O1 C2 C3 C4 3.5(4) . . . . ? C1 C2 C3 C4 -176.5(2) . . . . ? C8 C3 C4 C5 0.0(4) . . . . ? C2 C3 C4 C5 -179.8(2) . . . . ? C3 C4 C5 C6 0.3(4) . . . . ? C3 C4 C5 C11 179.5(3) . . . . ? C4 C5 C6 C7 -0.5(4) . . . . ? C11 C5 C6 C7 -179.7(3) . . . . ? C4 C5 C6 C12 177.7(2) . . . . ? C11 C5 C6 C12 -1.5(4) . . . . ? C5 C6 C7 C8 0.4(4) . . . . ? C12 C6 C7 C8 -177.8(2) . . . . ? C6 C7 C8 C3 -0.1(4) . . . . ? C6 C7 C8 C9 178.7(3) . . . . ? C4 C3 C8 C7 -0.2(4) . . . . ? C2 C3 C8 C7 179.7(2) . . . . ? C4 C3 C8 C9 -178.9(2) . . . . ? C2 C3 C8 C9 0.9(4) . . . . ? C7 C8 C9 O2 -5.0(4) . . . . ? C3 C8 C9 O2 173.8(3) . . . . ? C7 C8 C9 C10 174.6(2) . . . . ? C3 C8 C9 C10 -6.6(4) . . . . ? N1 C1 C10 C9 173.9(2) . . . . ? C2 C1 C10 C9 -3.8(4) . . . . ? N1 C1 C10 S1 1.7(4) . . . . ? C2 C1 C10 S1 -176.1(2) . . . . ? O2 C9 C10 C1 -172.2(3) . . . . ? C8 C9 C10 C1 8.1(4) . . . . ? O2 C9 C10 S1 -0.4(4) . . . . ? C8 C9 C10 S1 179.95(19) . . . . ? S2 S1 C10 C1 -1.7(2) . . . . ? S2 S1 C10 C9 -174.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.322 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.072