# Electronic Supplementary Material (ESI) for Chemical Science # 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_wk-30 #TrackingRef 'WK2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H38 F6 N4 O8 S2' _chemical_formula_weight 928.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.445(2) _cell_length_b 12.104(2) _cell_length_c 17.978(4) _cell_angle_alpha 77.35(3) _cell_angle_beta 76.40(3) _cell_angle_gamma 65.63(3) _cell_volume 2183.8(8) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9070 _exptl_absorpt_correction_T_max 0.9630 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17287 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7655 _reflns_number_gt 4022 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _platon_squeeze_details ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 0.500 110 19 ' ' ; _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^)+(0.2000P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7655 _refine_ls_number_parameters 559 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1603 _refine_ls_R_factor_gt 0.1054 _refine_ls_wR_factor_ref 0.3367 _refine_ls_wR_factor_gt 0.2949 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.002 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 C1 C -0.1102(5) 0.2755(5) 0.2011(4) 0.0839(16) Uani 1 1 d . . . H1 H -0.1316 0.2468 0.2528 0.101 Uiso 1 1 calc R . . C2 C -0.1880(7) 0.3909(7) 0.1690(6) 0.113(2) Uani 1 1 d . . . H2 H -0.2621 0.4402 0.1984 0.135 Uiso 1 1 calc R . . C3 C -0.1516(9) 0.4303(6) 0.0913(6) 0.113(3) Uani 1 1 d . . . H3 H -0.2017 0.5077 0.0692 0.136 Uiso 1 1 calc R . . C4 C -0.0491(8) 0.3614(6) 0.0487(4) 0.098(2) Uani 1 1 d . . . H4 H -0.0277 0.3887 -0.0032 0.118 Uiso 1 1 calc R . . C5 C 0.0258(6) 0.2492(5) 0.0813(3) 0.0791(15) Uani 1 1 d . . . H5 H 0.0991 0.2010 0.0507 0.095 Uiso 1 1 calc R . . C6 C -0.0021(5) 0.2045(5) 0.1565(3) 0.0646(13) Uani 1 1 d . . . C7 C 0.1120(5) -0.0122(4) 0.1454(3) 0.0650(13) Uani 1 1 d . . . C8 C 0.0137(6) -0.0269(5) 0.1213(3) 0.0775(15) Uani 1 1 d . . . H8 H -0.0723 0.0244 0.1354 0.093 Uiso 1 1 calc R . . C9 C 0.0418(7) -0.1165(6) 0.0769(4) 0.0891(18) Uani 1 1 d . . . H9 H -0.0252 -0.1251 0.0609 0.107 Uiso 1 1 calc R . . C10 C 0.1673(7) -0.1928(5) 0.0562(4) 0.0911(18) Uani 1 1 d . . . H10 H 0.1863 -0.2535 0.0262 0.109 Uiso 1 1 calc R . . C11 C 0.2665(6) -0.1789(5) 0.0805(4) 0.0890(18) Uani 1 1 d . . . H11 H 0.3522 -0.2314 0.0670 0.107 Uiso 1 1 calc R . . C12 C 0.2397(5) -0.0884(5) 0.1243(3) 0.0728(14) Uani 1 1 d . . . H12 H 0.3068 -0.0787 0.1394 0.087 Uiso 1 1 calc R . . C13 C 0.1407(4) 0.0725(4) 0.2503(3) 0.0620(12) Uani 1 1 d . . . C14 C 0.1980(5) -0.0424(4) 0.2924(3) 0.0635(12) Uani 1 1 d . . . H14 H 0.1888 -0.1101 0.2821 0.076 Uiso 1 1 calc R . . C15 C 0.2678(5) -0.0563(4) 0.3491(3) 0.0628(12) Uani 1 1 d . . . H15 H 0.3055 -0.1335 0.3763 0.075 Uiso 1 1 calc R . . C16 C 0.2829(4) 0.0439(4) 0.3663(3) 0.0588(11) Uani 1 1 d . . . C17 C 0.2200(5) 0.1573(4) 0.3269(3) 0.0649(13) Uani 1 1 d . . . H17 H 0.2250 0.2259 0.3391 0.078 Uiso 1 1 calc R . . C18 C 0.1503(5) 0.1725(4) 0.2704(3) 0.0643(13) Uani 1 1 d . . . H18 H 0.1090 0.2506 0.2453 0.077 Uiso 1 1 calc R . . C19 C 0.3651(4) 0.0279(4) 0.4213(3) 0.0595(12) Uani 1 1 d . . . C20 C 0.4766(4) 0.0575(4) 0.5094(3) 0.0621(12) Uani 1 1 d . . . C21 C 0.4259(6) 0.7248(5) 0.8682(3) 0.0811(16) Uani 1 1 d . . . H21 H 0.3433 0.7446 0.8576 0.097 Uiso 1 1 calc R . . C22 C 0.4929(8) 0.6094(6) 0.9034(4) 0.101(2) Uani 1 1 d . . . H22 H 0.4552 0.5513 0.9168 0.122 Uiso 1 1 calc R . . C23 C 0.6170(8) 0.5793(6) 0.9188(4) 0.098(2) Uani 1 1 d . . . H23 H 0.6636 0.5006 0.9410 0.118 Uiso 1 1 calc R . . C24 C 0.6697(7) 0.6663(6) 0.9012(4) 0.0925(19) Uani 1 1 d . . . H24 H 0.7510 0.6482 0.9131 0.111 Uiso 1 1 calc R . . C25 C 0.6023(5) 0.7801(5) 0.8658(3) 0.0723(14) Uani 1 1 d . . . H25 H 0.6395 0.8385 0.8530 0.087 Uiso 1 1 calc R . . C26 C 0.4815(5) 0.8104(5) 0.8488(3) 0.0659(13) Uani 1 1 d . . . C27 C 0.4099(5) 1.0310(5) 0.8400(3) 0.0684(14) Uani 1 1 d . . . C28 C 0.3790(6) 1.0382(6) 0.9188(3) 0.0905(19) Uani 1 1 d . . . H28 H 0.3596 0.9760 0.9529 0.109 Uiso 1 1 calc R . . C29 C 0.3767(7) 1.1337(8) 0.9463(5) 0.109(3) Uani 1 1 d . . . H29 H 0.3575 1.1355 0.9994 0.131 Uiso 1 1 calc R . . C30 C 0.4017(7) 1.2273(8) 0.8988(7) 0.115(3) Uani 1 1 d . . . H30 H 0.3996 1.2929 0.9188 0.138 Uiso 1 1 calc R . . C31 C 0.4297(7) 1.2242(6) 0.8216(6) 0.109(2) Uani 1 1 d . . . H31 H 0.4450 1.2893 0.7886 0.131 Uiso 1 1 calc R . . C32 C 0.4363(5) 1.1244(5) 0.7901(4) 0.0823(16) Uani 1 1 d . . . H32 H 0.4578 1.1219 0.7371 0.099 Uiso 1 1 calc R . . C33 C 0.3495(5) 0.9459(4) 0.7503(3) 0.0607(12) Uani 1 1 d . . . C34 C 0.2407(5) 1.0537(5) 0.7368(3) 0.0719(14) Uani 1 1 d . . . H34 H 0.2156 1.1171 0.7658 0.086 Uiso 1 1 calc R . . C35 C 0.1719(5) 1.0651(5) 0.6809(3) 0.0705(14) Uani 1 1 d . . . H35 H 0.0993 1.1364 0.6731 0.085 Uiso 1 1 calc R . . C36 C 0.2064(5) 0.9741(5) 0.6355(3) 0.0632(12) Uani 1 1 d . . . C37 C 0.3159(5) 0.8690(4) 0.6480(3) 0.0629(12) Uani 1 1 d . . . H37 H 0.3419 0.8064 0.6182 0.076 Uiso 1 1 calc R . . C38 C 0.3853(5) 0.8568(5) 0.7034(3) 0.0644(12) Uani 1 1 d . . . H38 H 0.4591 0.7862 0.7098 0.077 Uiso 1 1 calc R . . C39 C 0.1265(5) 0.9839(6) 0.5799(3) 0.0751(12) Uani 1 1 d U . . C40 C -0.0258(5) 1.0611(4) 0.4963(3) 0.0660(13) Uani 1 1 d . . . C41 C 0.376(2) 0.5324(12) 0.3225(10) 0.202(7) Uani 1 1 d U . . C42 C 0.3714(13) 0.5169(11) 0.4069(9) 0.169(4) Uani 1 1 d U . . C43 C 0.9922(16) 0.5859(13) 0.2258(11) 0.173(5) Uani 1 1 d . . . C44 C 0.8951(15) 0.5571(9) 0.2885(8) 0.151(4) Uani 1 1 d . . . F1 F 0.3187(16) 0.6356(10) 0.2942(8) 0.379(10) Uani 1 1 d . . . F2 F 0.3312(11) 0.4550(11) 0.3049(6) 0.251(4) Uani 1 1 d . . . F3 F 0.4985(15) 0.4944(14) 0.2891(9) 0.377(9) Uani 1 1 d . . . F4 F 0.9218(13) 0.6539(13) 0.1670(5) 0.274(5) Uani 1 1 d . . . F5 F 1.0756(12) 0.5060(9) 0.1952(11) 0.446(14) Uani 1 1 d . . . F6 F 1.0279(9) 0.6672(8) 0.2355(6) 0.225(4) Uani 1 1 d . . . N1 N 0.0792(4) 0.0852(4) 0.1885(2) 0.0672(11) Uani 1 1 d . . . N2 N 0.4633(4) -0.0796(4) 0.4410(2) 0.0632(10) Uani 1 1 d . . . H2A H 0.4837 -0.1484 0.4254 0.076 Uiso 1 1 calc R . . N3 N 0.4130(4) 0.9299(4) 0.8112(2) 0.0699(11) Uani 1 1 d . . . N4 N 0.1273(2) 0.8613(3) 0.55528(15) 0.0982(8) Uani 0.50 1 d PU . . H4A H 0.1686 0.7839 0.5668 0.118 Uiso 0.50 1 calc PR . . N4' N 0.02215(19) 1.1282(2) 0.54390(12) 0.0711(6) Uani 0.50 1 d P . . H4' H 0.0042 1.2026 0.5492 0.085 Uiso 0.50 1 calc PR . . O1 O 0.4292(13) 0.4133(9) 0.4364(7) 0.251(5) Uani 1 1 d . . . O2 O 0.3077(13) 0.6105(10) 0.4312(9) 0.296(7) Uani 1 1 d . . . O3 O 0.8018(8) 0.6409(11) 0.3122(5) 0.218(4) Uani 1 1 d . . . O4 O 0.938(2) 0.4533(8) 0.3140(6) 0.423(15) Uani 1 1 d . . . O5 O 0.5781(7) 0.6809(6) 0.4134(4) 0.160(2) Uani 1 1 d . . . O6 O 0.2386(13) 0.6451(9) 0.5823(8) 0.269(6) Uani 1 1 d . . . S1 S 0.34904(12) 0.15158(12) 0.46303(8) 0.0686(5) Uani 1 1 d . . . S2 S 0.02215(19) 1.1282(2) 0.54390(12) 0.0711(6) Uani 0.50 1 d P . . S2' S 0.1273(2) 0.8613(3) 0.55528(15) 0.0982(8) Uani 0.50 1 d PU . . 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 C1 0.066(3) 0.086(4) 0.088(4) -0.012(3) -0.023(3) -0.012(3) C2 0.078(4) 0.105(5) 0.144(7) -0.039(5) -0.035(4) -0.004(4) C3 0.137(6) 0.075(4) 0.138(7) 0.002(5) -0.089(6) -0.023(4) C4 0.139(6) 0.076(4) 0.085(4) 0.002(3) -0.044(4) -0.039(4) C5 0.086(4) 0.083(4) 0.072(4) 0.003(3) -0.027(3) -0.034(3) C6 0.068(3) 0.066(3) 0.065(3) -0.008(3) -0.023(2) -0.023(2) C7 0.081(3) 0.064(3) 0.051(3) 0.002(2) -0.026(2) -0.025(3) C8 0.080(3) 0.084(4) 0.080(4) -0.008(3) -0.026(3) -0.037(3) C9 0.112(5) 0.082(4) 0.092(4) -0.006(3) -0.036(4) -0.048(4) C10 0.123(5) 0.071(3) 0.082(4) -0.018(3) -0.030(4) -0.029(4) C11 0.091(4) 0.082(4) 0.082(4) -0.024(3) -0.015(3) -0.014(3) C12 0.074(3) 0.075(3) 0.074(3) -0.017(3) -0.019(3) -0.024(3) C13 0.058(3) 0.071(3) 0.056(3) -0.008(2) -0.016(2) -0.020(2) C14 0.072(3) 0.063(3) 0.057(3) 0.002(2) -0.026(2) -0.024(2) C15 0.063(3) 0.063(3) 0.053(3) 0.002(2) -0.013(2) -0.018(2) C16 0.057(2) 0.071(3) 0.048(3) -0.009(2) -0.012(2) -0.023(2) C17 0.072(3) 0.060(3) 0.066(3) -0.009(2) -0.021(2) -0.023(2) C18 0.068(3) 0.055(3) 0.063(3) -0.003(2) -0.029(2) -0.009(2) C19 0.057(3) 0.066(3) 0.049(3) -0.004(2) -0.008(2) -0.019(2) C20 0.062(3) 0.065(3) 0.057(3) -0.004(2) -0.015(2) -0.021(2) C21 0.090(4) 0.085(4) 0.071(4) 0.008(3) -0.029(3) -0.036(3) C22 0.136(6) 0.090(4) 0.088(5) 0.006(4) -0.035(4) -0.052(4) C23 0.130(6) 0.070(4) 0.079(4) 0.004(3) -0.037(4) -0.020(4) C24 0.096(4) 0.086(4) 0.087(4) -0.016(3) -0.037(3) -0.012(4) C25 0.073(3) 0.081(3) 0.061(3) -0.009(3) -0.018(3) -0.025(3) C26 0.079(3) 0.071(3) 0.047(3) -0.005(2) -0.018(2) -0.026(3) C27 0.065(3) 0.071(3) 0.069(3) -0.012(3) -0.025(2) -0.017(3) C28 0.090(4) 0.111(5) 0.061(3) -0.024(3) -0.022(3) -0.018(3) C29 0.099(5) 0.116(6) 0.105(6) -0.058(5) -0.042(4) -0.001(4) C30 0.097(5) 0.092(5) 0.164(9) -0.061(6) -0.062(5) -0.001(4) C31 0.098(5) 0.072(4) 0.167(8) -0.010(4) -0.043(5) -0.034(3) C32 0.077(3) 0.080(4) 0.090(4) -0.004(3) -0.022(3) -0.030(3) C33 0.063(3) 0.067(3) 0.054(3) -0.002(2) -0.018(2) -0.025(2) C34 0.078(3) 0.073(3) 0.066(3) -0.017(3) -0.023(3) -0.021(3) C35 0.071(3) 0.068(3) 0.067(3) -0.008(3) -0.028(3) -0.013(2) C36 0.067(3) 0.077(3) 0.050(3) 0.000(2) -0.017(2) -0.033(3) C37 0.067(3) 0.065(3) 0.054(3) -0.007(2) -0.015(2) -0.020(2) C38 0.066(3) 0.070(3) 0.055(3) -0.011(2) -0.013(2) -0.021(2) C39 0.055(3) 0.111(3) 0.042(3) 0.004(2) -0.005(2) -0.023(3) C40 0.078(3) 0.065(3) 0.056(3) -0.006(2) -0.010(2) -0.031(3) C41 0.252(17) 0.111(8) 0.187(9) -0.028(9) 0.043(13) -0.051(10) C42 0.196(11) 0.102(7) 0.204(9) -0.041(9) 0.003(10) -0.061(8) C43 0.191(13) 0.128(9) 0.177(13) -0.043(9) 0.024(11) -0.054(10) C44 0.183(11) 0.097(7) 0.157(10) -0.032(7) -0.080(9) -0.002(7) F1 0.53(2) 0.147(7) 0.289(14) 0.026(8) -0.042(13) 0.000(10) F2 0.300(12) 0.241(9) 0.232(9) -0.054(7) -0.038(8) -0.115(8) F3 0.355(15) 0.393(17) 0.366(17) -0.194(14) 0.197(14) -0.192(13) F4 0.344(13) 0.374(14) 0.152(7) -0.008(8) 0.004(8) -0.222(12) F5 0.287(12) 0.179(7) 0.70(3) -0.177(13) 0.250(17) -0.037(7) F6 0.252(9) 0.181(6) 0.276(10) -0.036(6) -0.029(7) -0.119(6) N1 0.077(3) 0.062(2) 0.060(2) -0.0070(19) -0.032(2) -0.013(2) N2 0.067(2) 0.075(3) 0.049(2) -0.0116(19) -0.0156(18) -0.024(2) N3 0.084(3) 0.073(3) 0.059(2) -0.008(2) -0.028(2) -0.027(2) N4 0.0916(16) 0.136(2) 0.0718(15) -0.0072(14) -0.0328(12) -0.0408(15) N4' 0.0755(12) 0.0912(14) 0.0605(12) -0.0121(10) -0.0181(10) -0.0406(11) O1 0.312(13) 0.147(7) 0.231(11) -0.021(7) 0.014(9) -0.060(8) O2 0.340(16) 0.155(7) 0.385(19) -0.121(10) -0.020(13) -0.065(9) O3 0.145(6) 0.241(10) 0.185(8) 0.012(7) -0.007(6) -0.023(6) O4 0.88(4) 0.091(5) 0.168(9) -0.017(5) -0.073(14) -0.064(11) O5 0.164(5) 0.129(4) 0.180(6) -0.043(4) -0.020(5) -0.042(4) O6 0.293(12) 0.167(7) 0.363(16) -0.039(9) -0.111(11) -0.070(8) S1 0.0666(8) 0.0670(8) 0.0665(8) -0.0108(6) -0.0219(6) -0.0131(6) S2 0.0755(12) 0.0912(14) 0.0605(12) -0.0121(10) -0.0181(10) -0.0406(11) S2' 0.0916(16) 0.136(2) 0.0718(15) -0.0072(14) -0.0328(12) -0.0408(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 C1 C6 1.367(7) . ? C1 C2 1.393(9) . ? C2 C3 1.397(11) . ? C3 C4 1.306(11) . ? C4 C5 1.360(8) . ? C5 C6 1.357(8) . ? C6 N1 1.436(6) . ? C7 C12 1.382(7) . ? C7 C8 1.383(7) . ? C7 N1 1.424(6) . ? C8 C9 1.374(8) . ? C9 C10 1.364(9) . ? C10 C11 1.390(9) . ? C11 C12 1.378(7) . ? C13 C18 1.388(7) . ? C13 C14 1.399(7) . ? C13 N1 1.400(6) . ? C14 C15 1.380(7) . ? C15 C16 1.399(7) . ? C16 C17 1.380(7) . ? C16 C19 1.451(7) . ? C17 C18 1.371(7) . ? C19 N2 1.364(6) . ? C19 S1 1.743(5) . ? C20 C20 1.359(9) 2_656 ? C20 N2 1.372(6) 2_656 ? C20 S1 1.705(5) . ? C21 C26 1.371(8) . ? C21 C22 1.377(8) . ? C22 C23 1.394(10) . ? C23 C24 1.363(10) . ? C24 C25 1.367(8) . ? C25 C26 1.369(7) . ? C26 N3 1.431(6) . ? C27 C32 1.372(8) . ? C27 C28 1.389(8) . ? C27 N3 1.414(6) . ? C28 C29 1.342(10) . ? C29 C30 1.350(12) . ? C30 C31 1.355(12) . ? C31 C32 1.411(9) . ? C33 C38 1.384(7) . ? C33 N3 1.389(6) . ? C33 C34 1.405(7) . ? C34 C35 1.369(7) . ? C35 C36 1.383(7) . ? C36 C37 1.389(7) . ? C36 C39 1.463(7) . ? C37 C38 1.362(7) . ? C39 N4 1.635(7) . ? C39 N4' 1.744(6) . ? C40 C40 1.335(10) 2_576 ? C40 S2' 1.522(6) 2_576 ? C40 N4 1.522(6) 2_576 ? C40 N4' 1.608(6) . ? C41 F1 1.205(15) . ? C41 F3 1.316(19) . ? C41 F2 1.358(18) . ? C41 C42 1.478(19) . ? C42 O2 1.179(12) . ? C42 O1 1.217(13) . ? C43 F5 1.172(13) . ? C43 F6 1.268(15) . ? C43 F4 1.383(17) . ? C43 C44 1.479(18) . ? C44 O4 1.172(11) . ? C44 O3 1.197(11) . ? N2 C20 1.372(6) 2_656 ? N4 C40 1.522(6) 2_576 ? 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 C6 C1 C2 119.8(7) . . ? C1 C2 C3 118.1(6) . . ? C4 C3 C2 121.8(6) . . ? C3 C4 C5 119.2(7) . . ? C6 C5 C4 122.7(6) . . ? C5 C6 C1 118.5(5) . . ? C5 C6 N1 120.9(5) . . ? C1 C6 N1 120.7(5) . . ? C12 C7 C8 119.5(5) . . ? C12 C7 N1 121.6(5) . . ? C8 C7 N1 118.9(5) . . ? C9 C8 C7 120.7(6) . . ? C10 C9 C8 120.3(6) . . ? C9 C10 C11 119.3(5) . . ? C12 C11 C10 120.9(6) . . ? C11 C12 C7 119.3(5) . . ? C18 C13 C14 117.9(4) . . ? C18 C13 N1 121.3(4) . . ? C14 C13 N1 120.8(4) . . ? C15 C14 C13 120.8(5) . . ? C14 C15 C16 121.0(4) . . ? C17 C16 C15 117.3(4) . . ? C17 C16 C19 121.6(4) . . ? C15 C16 C19 121.1(4) . . ? C18 C17 C16 122.3(5) . . ? C17 C18 C13 120.7(4) . . ? N2 C19 C16 124.1(4) . . ? N2 C19 S1 115.1(3) . . ? C16 C19 S1 120.7(3) . . ? C20 C20 N2 118.0(5) 2_656 2_656 ? C20 C20 S1 110.5(5) 2_656 . ? N2 C20 S1 131.4(4) 2_656 . ? C26 C21 C22 119.8(6) . . ? C21 C22 C23 120.2(7) . . ? C24 C23 C22 119.5(6) . . ? C23 C24 C25 119.6(6) . . ? C24 C25 C26 121.6(6) . . ? C25 C26 C21 119.3(5) . . ? C25 C26 N3 120.8(5) . . ? C21 C26 N3 119.9(5) . . ? C32 C27 C28 119.0(6) . . ? C32 C27 N3 120.2(5) . . ? C28 C27 N3 120.8(6) . . ? C29 C28 C27 121.0(7) . . ? C28 C29 C30 121.5(7) . . ? C29 C30 C31 119.0(7) . . ? C30 C31 C32 121.5(8) . . ? C27 C32 C31 118.0(7) . . ? C38 C33 N3 122.6(4) . . ? C38 C33 C34 117.5(4) . . ? N3 C33 C34 119.8(4) . . ? C35 C34 C33 119.7(5) . . ? C34 C35 C36 122.3(5) . . ? C35 C36 C37 117.7(4) . . ? C35 C36 C39 121.6(5) . . ? C37 C36 C39 120.6(5) . . ? C38 C37 C36 120.5(4) . . ? C37 C38 C33 122.2(4) . . ? C36 C39 N4 120.8(4) . . ? C36 C39 N4' 119.4(5) . . ? N4 C39 N4' 119.7(3) . . ? C40 C40 S2' 122.7(6) 2_576 2_576 ? C40 C40 N4 122.7(6) 2_576 2_576 ? S2' C40 N4 0.00(18) 2_576 2_576 ? C40 C40 N4' 118.2(6) 2_576 . ? S2' C40 N4' 119.0(3) 2_576 . ? N4 C40 N4' 119.0(3) 2_576 . ? F1 C41 F3 109.5(16) . . ? F1 C41 F2 110(2) . . ? F3 C41 F2 103.6(12) . . ? F1 C41 C42 114.6(14) . . ? F3 C41 C42 108.6(19) . . ? F2 C41 C42 110.2(13) . . ? O2 C42 O1 134.0(18) . . ? O2 C42 C41 110.6(15) . . ? O1 C42 C41 115.4(12) . . ? F5 C43 F6 114.0(16) . . ? F5 C43 F4 102.3(17) . . ? F6 C43 F4 97.3(12) . . ? F5 C43 C44 118.9(13) . . ? F6 C43 C44 115.8(13) . . ? F4 C43 C44 104.1(13) . . ? O4 C44 O3 131.2(19) . . ? O4 C44 C43 109.7(16) . . ? O3 C44 C43 117.8(12) . . ? C13 N1 C7 122.6(4) . . ? C13 N1 C6 120.0(4) . . ? C7 N1 C6 116.4(4) . . ? C19 N2 C20 107.3(4) . 2_656 ? C33 N3 C27 121.4(4) . . ? C33 N3 C26 121.3(4) . . ? C27 N3 C26 117.2(4) . . ? C40 N4 C39 91.2(3) 2_576 . ? C40 N4' C39 88.1(3) . . ? C20 S1 C19 89.0(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.803 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.089 _database_code_depnum_ccdc_archive 'CCDC 930941' ####################################################################### # # 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_1 #TrackingRef 'wk1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H28 N4 S2' _chemical_formula_sum 'C40 H28 N4 S2' _chemical_formula_weight 628.78 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' 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 9.6569(19) _cell_length_b 10.140(2) _cell_length_c 18.898(5) _cell_angle_alpha 90.00 _cell_angle_beta 118.42(2) _cell_angle_gamma 90.00 _cell_volume 1627.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.199 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9556 _exptl_absorpt_correction_T_max 0.9639 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12103 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2848 _reflns_number_gt 2108 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0409P)^2^+0.3560P] 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 2848 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1000 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.50672(7) -0.89513(6) -0.09087(3) 0.0614(2) Uani 1 1 d . . . N1 N 0.40307(18) -0.85809(16) 0.01210(9) 0.0489(4) Uani 1 1 d . . . N2 N 0.17018(19) -0.29462(17) -0.17091(10) 0.0544(5) Uani 1 1 d . . . C1 C 0.4133(2) -0.80121(19) -0.04756(11) 0.0441(5) Uani 1 1 d . . . C2 C 0.2042(2) -0.23509(19) -0.22968(12) 0.0465(5) Uani 1 1 d . . . C3 C 0.2561(2) -0.4584(2) -0.06362(11) 0.0511(5) Uani 1 1 d . . . H1 H 0.2314 -0.4010 -0.0329 0.061 Uiso 1 1 calc R . . C4 C 0.3147(2) -0.5811(2) -0.03406(12) 0.0493(5) Uani 1 1 d . . . H3 H 0.3289 -0.6055 0.0164 0.059 Uiso 1 1 calc R . . C5 C 0.3535(2) -0.66985(19) -0.07816(11) 0.0427(4) Uani 1 1 d . . . C6 C 0.5304(2) -1.0197(2) -0.02431(11) 0.0461(5) Uani 1 1 d . . . C7 C 0.3322(2) -0.6283(2) -0.15301(11) 0.0486(5) Uani 1 1 d . . . H2 H 0.3585 -0.6852 -0.1833 0.058 Uiso 1 1 calc R . . C8 C 0.2328(2) -0.41850(19) -0.13949(11) 0.0461(5) Uani 1 1 d . . . C9 C 0.0663(2) -0.2287(2) -0.14851(12) 0.0502(5) Uani 1 1 d . . . C10 C 0.2736(2) -0.5059(2) -0.18318(11) 0.0498(5) Uani 1 1 d . . . H4 H 0.2609 -0.4812 -0.2333 0.060 Uiso 1 1 calc R . . C11 C 0.0902(3) -0.0986(2) -0.12595(13) 0.0650(6) Uani 1 1 d . . . H7 H 0.1720 -0.0520 -0.1272 0.078 Uiso 1 1 calc R . . C12 C 0.0865(3) -0.2049(2) -0.30466(14) 0.0653(6) Uani 1 1 d . . . H5 H -0.0181 -0.2207 -0.3181 0.078 Uiso 1 1 calc R . . C13 C 0.3938(3) -0.1527(3) -0.26560(16) 0.0792(8) Uani 1 1 d . . . H11 H 0.4980 -0.1340 -0.2515 0.095 Uiso 1 1 calc R . . C14 C -0.0586(3) -0.2966(3) -0.14887(15) 0.0716(7) Uani 1 1 d . . . H8 H -0.0779 -0.3840 -0.1658 0.086 Uiso 1 1 calc R . . C15 C 0.3579(2) -0.2084(2) -0.21012(14) 0.0629(6) Uani 1 1 d . . . H6 H 0.4383 -0.2283 -0.1589 0.076 Uiso 1 1 calc R . . C16 C -0.1542(3) -0.2330(4) -0.12376(19) 0.0985(11) Uani 1 1 d . . . H14 H -0.2370 -0.2784 -0.1229 0.118 Uiso 1 1 calc R . . C17 C 0.2781(4) -0.1247(3) -0.34074(17) 0.0821(8) Uani 1 1 d . . . H10 H 0.3031 -0.0883 -0.3784 0.098 Uiso 1 1 calc R . . C18 C -0.0073(4) -0.0367(3) -0.10143(15) 0.0901(9) Uani 1 1 d . . . H13 H 0.0096 0.0512 -0.0857 0.108 Uiso 1 1 calc R . . C19 C 0.1246(3) -0.1499(3) -0.36116(15) 0.0827(8) Uani 1 1 d . . . H9 H 0.0452 -0.1305 -0.4127 0.099 Uiso 1 1 calc R . . C20 C -0.1284(4) -0.1044(4) -0.10030(17) 0.1053(13) Uani 1 1 d . . . H12 H -0.1934 -0.0627 -0.0835 0.126 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 0.0824(4) 0.0568(4) 0.0670(4) 0.0189(3) 0.0535(3) 0.0223(3) N1 0.0548(9) 0.0490(10) 0.0503(10) 0.0085(8) 0.0310(8) 0.0102(8) N2 0.0627(10) 0.0543(11) 0.0660(11) 0.0197(9) 0.0466(9) 0.0208(8) C1 0.0393(9) 0.0499(12) 0.0440(11) 0.0028(9) 0.0206(9) 0.0039(8) C2 0.0540(11) 0.0438(12) 0.0522(12) 0.0059(9) 0.0338(10) 0.0102(9) C3 0.0577(12) 0.0538(13) 0.0489(12) 0.0032(10) 0.0312(10) 0.0120(10) C4 0.0527(11) 0.0576(14) 0.0413(11) 0.0059(9) 0.0255(9) 0.0076(10) C5 0.0376(9) 0.0479(12) 0.0417(10) 0.0040(9) 0.0181(8) 0.0035(8) C6 0.0482(10) 0.0484(12) 0.0470(11) 0.0071(9) 0.0268(9) 0.0069(9) C7 0.0544(11) 0.0497(13) 0.0476(11) 0.0009(9) 0.0290(10) 0.0071(9) C8 0.0442(10) 0.0491(12) 0.0506(12) 0.0075(9) 0.0271(9) 0.0073(9) C9 0.0488(11) 0.0591(14) 0.0493(12) 0.0124(10) 0.0287(9) 0.0163(10) C10 0.0558(11) 0.0557(13) 0.0434(11) 0.0061(9) 0.0281(10) 0.0100(10) C11 0.0670(14) 0.0701(17) 0.0562(14) -0.0005(12) 0.0280(12) 0.0152(12) C12 0.0586(13) 0.0745(17) 0.0653(15) 0.0183(12) 0.0315(12) 0.0230(12) C13 0.0816(17) 0.099(2) 0.0797(18) 0.0032(16) 0.0566(16) -0.0052(15) C14 0.0617(13) 0.0797(18) 0.0875(18) 0.0271(14) 0.0471(14) 0.0163(12) C15 0.0573(12) 0.0838(17) 0.0551(13) 0.0008(12) 0.0328(11) -0.0002(12) C16 0.0764(17) 0.142(3) 0.109(2) 0.060(2) 0.0700(18) 0.043(2) C17 0.111(2) 0.0819(19) 0.089(2) 0.0216(15) 0.0768(19) 0.0211(16) C18 0.112(2) 0.097(2) 0.0643(17) -0.0032(15) 0.0441(17) 0.0431(19) C19 0.0974(19) 0.093(2) 0.0596(15) 0.0307(14) 0.0385(14) 0.0409(16) C20 0.108(2) 0.158(4) 0.0758(19) 0.036(2) 0.0644(18) 0.077(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C6 1.7192(19) . ? S1 C1 1.7588(18) . ? N1 C1 1.311(2) . ? N1 C6 1.364(2) 3_635 ? N2 C8 1.398(2) . ? N2 C9 1.427(2) . ? N2 C2 1.433(2) . ? C1 C5 1.457(3) . ? C2 C12 1.364(3) . ? C2 C15 1.375(3) . ? C3 C4 1.370(3) . ? C3 C8 1.401(3) . ? C3 H1 0.9300 . ? C4 C5 1.394(3) . ? C4 H3 0.9300 . ? C5 C7 1.394(3) . ? C6 C6 1.364(3) 3_635 ? C6 N1 1.364(2) 3_635 ? C7 C10 1.370(3) . ? C7 H2 0.9300 . ? C8 C10 1.390(3) . ? C9 C11 1.372(3) . ? C9 C14 1.386(3) . ? C10 H4 0.9300 . ? C11 C18 1.382(3) . ? C11 H7 0.9300 . ? C12 C19 1.400(3) . ? C12 H5 0.9300 . ? C13 C17 1.355(4) . ? C13 C15 1.373(3) . ? C13 H11 0.9300 . ? C14 C16 1.382(4) . ? C14 H8 0.9300 . ? C15 H6 0.9300 . ? C16 C20 1.361(5) . ? C16 H14 0.9300 . ? C17 C19 1.366(4) . ? C17 H10 0.9300 . ? C18 C20 1.365(4) . ? C18 H13 0.9300 . ? C19 H9 0.9300 . ? C20 H12 0.9300 . ? 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 C6 S1 C1 88.64(9) . . ? C1 N1 C6 108.83(15) . 3_635 ? C8 N2 C9 121.19(15) . . ? C8 N2 C2 119.69(14) . . ? C9 N2 C2 119.04(15) . . ? N1 C1 C5 124.43(16) . . ? N1 C1 S1 115.29(14) . . ? C5 C1 S1 120.28(13) . . ? C12 C2 C15 119.66(19) . . ? C12 C2 N2 120.94(18) . . ? C15 C2 N2 119.40(19) . . ? C4 C3 C8 120.90(18) . . ? C4 C3 H1 119.6 . . ? C8 C3 H1 119.6 . . ? C3 C4 C5 121.26(18) . . ? C3 C4 H3 119.4 . . ? C5 C4 H3 119.4 . . ? C7 C5 C4 117.35(18) . . ? C7 C5 C1 121.22(17) . . ? C4 C5 C1 121.44(16) . . ? C6 C6 N1 118.1(2) 3_635 3_635 ? C6 C6 S1 109.15(19) 3_635 . ? N1 C6 S1 132.75(13) 3_635 . ? C10 C7 C5 121.88(18) . . ? C10 C7 H2 119.1 . . ? C5 C7 H2 119.1 . . ? C10 C8 N2 120.55(17) . . ? C10 C8 C3 118.06(18) . . ? N2 C8 C3 121.39(17) . . ? C11 C9 C14 119.8(2) . . ? C11 C9 N2 120.33(19) . . ? C14 C9 N2 119.9(2) . . ? C7 C10 C8 120.54(18) . . ? C7 C10 H4 119.7 . . ? C8 C10 H4 119.7 . . ? C9 C11 C18 120.0(2) . . ? C9 C11 H7 120.0 . . ? C18 C11 H7 120.0 . . ? C2 C12 C19 119.3(2) . . ? C2 C12 H5 120.3 . . ? C19 C12 H5 120.3 . . ? C17 C13 C15 120.3(2) . . ? C17 C13 H11 119.9 . . ? C15 C13 H11 119.9 . . ? C16 C14 C9 119.2(3) . . ? C16 C14 H8 120.4 . . ? C9 C14 H8 120.4 . . ? C13 C15 C2 120.5(2) . . ? C13 C15 H6 119.7 . . ? C2 C15 H6 119.7 . . ? C20 C16 C14 120.7(3) . . ? C20 C16 H14 119.7 . . ? C14 C16 H14 119.7 . . ? C13 C17 C19 120.0(2) . . ? C13 C17 H10 120.0 . . ? C19 C17 H10 120.0 . . ? C20 C18 C11 120.2(3) . . ? C20 C18 H13 119.9 . . ? C11 C18 H13 119.9 . . ? C17 C19 C12 120.2(2) . . ? C17 C19 H9 119.9 . . ? C12 C19 H9 119.9 . . ? C16 C20 C18 120.1(3) . . ? C16 C20 H12 119.9 . . ? C18 C20 H12 119.9 . . ? 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 N1 C1 C5 179.52(17) 3_635 . . . ? C6 N1 C1 S1 -0.5(2) 3_635 . . . ? C6 S1 C1 N1 0.79(16) . . . . ? C6 S1 C1 C5 -179.19(16) . . . . ? C8 N2 C2 C12 119.5(2) . . . . ? C9 N2 C2 C12 -57.5(3) . . . . ? C8 N2 C2 C15 -60.4(3) . . . . ? C9 N2 C2 C15 122.7(2) . . . . ? C8 C3 C4 C5 0.2(3) . . . . ? C3 C4 C5 C7 0.8(3) . . . . ? C3 C4 C5 C1 -178.90(18) . . . . ? N1 C1 C5 C7 -163.71(18) . . . . ? S1 C1 C5 C7 16.3(2) . . . . ? N1 C1 C5 C4 16.0(3) . . . . ? S1 C1 C5 C4 -164.03(15) . . . . ? C1 S1 C6 C6 -0.8(2) . . . 3_635 ? C1 S1 C6 N1 -179.8(2) . . . 3_635 ? C4 C5 C7 C10 -0.9(3) . . . . ? C1 C5 C7 C10 178.85(17) . . . . ? C9 N2 C8 C10 151.85(19) . . . . ? C2 N2 C8 C10 -25.0(3) . . . . ? C9 N2 C8 C3 -28.0(3) . . . . ? C2 N2 C8 C3 155.07(19) . . . . ? C4 C3 C8 C10 -1.2(3) . . . . ? C4 C3 C8 N2 178.74(18) . . . . ? C8 N2 C9 C11 132.2(2) . . . . ? C2 N2 C9 C11 -50.9(3) . . . . ? C8 N2 C9 C14 -47.3(3) . . . . ? C2 N2 C9 C14 129.6(2) . . . . ? C5 C7 C10 C8 -0.1(3) . . . . ? N2 C8 C10 C7 -178.79(18) . . . . ? C3 C8 C10 C7 1.1(3) . . . . ? C14 C9 C11 C18 1.9(3) . . . . ? N2 C9 C11 C18 -177.56(19) . . . . ? C15 C2 C12 C19 1.5(3) . . . . ? N2 C2 C12 C19 -178.4(2) . . . . ? C11 C9 C14 C16 -2.2(3) . . . . ? N2 C9 C14 C16 177.3(2) . . . . ? C17 C13 C15 C2 -0.8(4) . . . . ? C12 C2 C15 C13 -0.5(3) . . . . ? N2 C2 C15 C13 179.3(2) . . . . ? C9 C14 C16 C20 1.2(4) . . . . ? C15 C13 C17 C19 1.1(4) . . . . ? C9 C11 C18 C20 -0.6(4) . . . . ? C13 C17 C19 C12 -0.1(4) . . . . ? C2 C12 C19 C17 -1.2(4) . . . . ? C14 C16 C20 C18 0.1(4) . . . . ? C11 C18 C20 C16 -0.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.153 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 930942'