# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jan Jeppesen' _publ_contact_author_address ; SDU: Odense University Department of Physics and Chemistry Campusvej 55 Odense DK-5230 Odense M DENMARK ; _publ_contact_author_email JOJ@IFK.SDU.DK _publ_section_title ; A bromine catalysed dimerisation of alpha-alpha'-dihalomonopyrrolo-TTF ; loop_ _publ_author_name 'Jan Jeppesen' 'Hemant Gopee' 'Andrew D. Bond' 'Bo M. Petersen' #============================================================================= data_3a _database_code_depnum_ccdc_archive 'CCDC 649631' _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H25 Br2 N S6' _chemical_formula_sum 'C19 H25 Br2 N S6' _chemical_formula_weight 619.58 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M '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 17.5630(9) _cell_length_b 8.0200(4) _cell_length_c 17.9855(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.597(2) _cell_angle_gamma 90.00 _cell_volume 2525.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4845 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 19.40 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 3.714 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.489 _exptl_absorpt_correction_T_max 0.929 _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.526846 ; _exptl_special_details ? _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 33371 _diffrn_reflns_av_R_equivalents 0.0784 _diffrn_reflns_av_sigmaI/netI 0.0788 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 24.71 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.971 _reflns_number_total 4187 _reflns_number_gt 2641 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-22 (Bruker-Nonius, 2004)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a (Bruker, 2003)' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL v.6.10 (Sheldrick, 2000)' _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^)+(0.0471P)^2^] 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 4187 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0943 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.0984 _refine_ls_wR_factor_gt 0.0824 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.366 _refine_diff_density_min -0.529 _refine_diff_density_rms 0.092 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 0.32830(3) 0.89007(6) 0.40312(3) 0.04838(19) Uani 1 1 d . . . Br2 Br 0.49424(4) 0.82544(7) 0.68805(3) 0.0568(2) Uani 1 1 d . . . S1 S 0.51579(8) 0.67684(16) 0.38706(6) 0.0439(4) Uani 1 1 d . . . S2 S 0.60395(8) 0.64348(15) 0.53733(6) 0.0432(4) Uani 1 1 d . . . S3 S 0.66162(8) 0.52308(16) 0.31057(6) 0.0457(4) Uani 1 1 d . . . S4 S 0.74513(8) 0.48863(15) 0.45681(6) 0.0413(4) Uani 1 1 d . . . S5 S 0.80253(8) 0.57241(14) 0.22933(6) 0.0418(4) Uani 1 1 d . . . S6 S 0.89976(8) 0.52944(14) 0.39718(7) 0.0407(3) Uani 1 1 d . . . N1 N 0.4056(2) 0.8693(4) 0.5493(2) 0.0379(10) Uani 1 1 d . . . C1 C 0.4079(3) 0.8378(5) 0.4748(2) 0.0364(13) Uani 1 1 d . . . C2 C 0.4722(3) 0.8133(5) 0.5847(2) 0.0382(13) Uani 1 1 d . . . C3 C 0.4755(3) 0.7635(5) 0.4640(2) 0.0348(12) Uani 1 1 d . . . C4 C 0.5163(3) 0.7464(5) 0.5335(2) 0.0361(12) Uani 1 1 d . . . C5 C 0.6005(3) 0.6161(5) 0.4397(2) 0.0353(12) Uani 1 1 d . . . C6 C 0.6593(3) 0.5504(5) 0.4075(2) 0.0366(12) Uani 1 1 d . . . C7 C 0.7611(3) 0.5490(5) 0.3136(2) 0.0376(13) Uani 1 1 d . . . C8 C 0.8008(3) 0.5314(5) 0.3809(3) 0.0367(12) Uani 1 1 d . . . C9 C 0.7545(3) 0.7607(6) 0.1941(3) 0.0458(14) Uani 1 1 d . . . H9A H 0.7670 0.7791 0.1420 0.055 Uiso 1 1 calc R . . H9B H 0.6986 0.7437 0.1934 0.055 Uiso 1 1 calc R . . C10 C 0.7759(3) 0.9175(5) 0.2397(3) 0.0495(15) Uani 1 1 d . . . H10A H 0.7471 1.0133 0.2170 0.059 Uiso 1 1 calc R . . H10B H 0.7598 0.9024 0.2908 0.059 Uiso 1 1 calc R . . C11 C 0.8600(3) 0.9588(5) 0.2448(3) 0.0450(14) Uani 1 1 d . . . H11A H 0.8770 0.9631 0.1937 0.054 Uiso 1 1 calc R . . H11B H 0.8883 0.8673 0.2717 0.054 Uiso 1 1 calc R . . C12 C 0.8815(4) 1.1218(6) 0.2838(3) 0.0545(17) Uani 1 1 d . . . H12A H 0.8542 1.2143 0.2568 0.065 Uiso 1 1 calc R . . H12B H 0.8646 1.1187 0.3350 0.065 Uiso 1 1 calc R . . C13 C 0.9661(4) 1.1561(6) 0.2880(3) 0.0607(17) Uani 1 1 d . . . H13A H 0.9773 1.2580 0.3169 0.091 Uiso 1 1 calc R . . H13B H 0.9823 1.1704 0.2375 0.091 Uiso 1 1 calc R . . H13C H 0.9938 1.0621 0.3123 0.091 Uiso 1 1 calc R . . C14 C 0.9132(3) 0.6648(5) 0.4781(2) 0.0384(13) Uani 1 1 d . . . H14A H 0.8840 0.6191 0.5184 0.046 Uiso 1 1 calc R . . H14B H 0.9679 0.6648 0.4962 0.046 Uiso 1 1 calc R . . C15 C 0.8879(3) 0.8425(5) 0.4623(2) 0.0378(13) Uani 1 1 d . . . H15A H 0.9175 0.8894 0.4226 0.045 Uiso 1 1 calc R . . H15B H 0.8332 0.8432 0.4439 0.045 Uiso 1 1 calc R . . C16 C 0.8991(3) 0.9506(5) 0.5308(2) 0.0434(14) Uani 1 1 d . . . H16A H 0.9532 0.9442 0.5507 0.052 Uiso 1 1 calc R . . H16B H 0.8675 0.9062 0.5695 0.052 Uiso 1 1 calc R . . C17 C 0.8781(3) 1.1329(5) 0.5164(2) 0.0411(13) Uani 1 1 d . . . H17A H 0.8239 1.1396 0.4967 0.049 Uiso 1 1 calc R . . H17B H 0.9097 1.1775 0.4778 0.049 Uiso 1 1 calc R . . C18 C 0.8898(3) 1.2413(6) 0.5863(2) 0.0526(16) Uani 1 1 d . . . H18A H 0.8761 1.3569 0.5737 0.079 Uiso 1 1 calc R . . H18B H 0.9434 1.2361 0.6059 0.079 Uiso 1 1 calc R . . H18C H 0.8573 1.2002 0.6242 0.079 Uiso 1 1 calc R . . C19 C 0.3428(3) 0.9529(6) 0.5853(3) 0.0480(14) Uani 1 1 d . . . H19A H 0.3169 1.0318 0.5501 0.072 Uiso 1 1 calc R . . H19B H 0.3638 1.0130 0.6297 0.072 Uiso 1 1 calc R . . H19C H 0.3062 0.8691 0.5997 0.072 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 0.0455(4) 0.0535(3) 0.0454(3) 0.0048(2) -0.0007(3) 0.0049(3) Br2 0.0619(5) 0.0740(4) 0.0342(3) -0.0085(3) 0.0024(3) -0.0067(3) S1 0.0418(10) 0.0571(8) 0.0324(7) -0.0010(6) 0.0015(6) 0.0032(7) S2 0.0452(10) 0.0498(8) 0.0339(7) 0.0028(6) -0.0004(6) 0.0022(7) S3 0.0439(11) 0.0550(8) 0.0379(7) -0.0053(6) 0.0017(6) -0.0035(7) S4 0.0412(10) 0.0429(7) 0.0399(7) 0.0050(6) 0.0038(6) 0.0010(6) S5 0.0504(11) 0.0380(7) 0.0373(7) -0.0038(5) 0.0062(6) 0.0023(6) S6 0.0405(10) 0.0354(7) 0.0460(8) -0.0026(6) 0.0021(6) 0.0025(6) N1 0.034(3) 0.041(2) 0.040(2) -0.0026(18) 0.007(2) -0.003(2) C1 0.040(4) 0.036(3) 0.033(3) 0.001(2) -0.001(2) -0.003(3) C2 0.048(4) 0.038(3) 0.029(3) -0.005(2) 0.003(3) -0.006(3) C3 0.043(4) 0.035(3) 0.027(3) 0.001(2) 0.005(2) -0.005(3) C4 0.034(4) 0.040(3) 0.034(3) 0.002(2) -0.002(2) -0.003(2) C5 0.042(4) 0.030(3) 0.034(3) 0.003(2) 0.002(2) -0.005(2) C6 0.038(4) 0.036(3) 0.036(3) 0.002(2) 0.007(2) -0.001(2) C7 0.045(4) 0.027(3) 0.041(3) -0.002(2) 0.002(3) 0.001(2) C8 0.038(4) 0.027(3) 0.045(3) -0.004(2) 0.006(2) 0.004(2) C9 0.045(4) 0.050(3) 0.043(3) 0.006(2) 0.000(3) 0.006(3) C10 0.065(5) 0.032(3) 0.051(3) 0.002(2) 0.005(3) 0.013(3) C11 0.061(5) 0.032(3) 0.042(3) 0.001(2) 0.005(3) 0.004(3) C12 0.084(6) 0.036(3) 0.042(3) 0.004(2) 0.002(3) 0.009(3) C13 0.081(6) 0.050(3) 0.051(3) -0.006(3) 0.002(3) -0.011(3) C14 0.044(4) 0.036(3) 0.035(3) 0.000(2) -0.004(2) -0.005(2) C15 0.043(4) 0.036(3) 0.034(3) -0.002(2) -0.002(2) -0.001(2) C16 0.056(4) 0.036(3) 0.038(3) -0.001(2) 0.007(3) -0.001(3) C17 0.048(4) 0.036(3) 0.039(3) 0.002(2) 0.000(2) -0.004(2) C18 0.078(5) 0.035(3) 0.045(3) -0.001(2) 0.007(3) -0.008(3) C19 0.048(4) 0.045(3) 0.052(3) -0.009(2) 0.012(3) -0.004(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 Br1 C1 1.872(5) . ? Br2 C2 1.871(4) . ? S1 C3 1.747(5) . ? S1 C5 1.766(5) . ? S2 C4 1.743(5) . ? S2 C5 1.767(4) . ? S3 C7 1.757(5) . ? S3 C6 1.761(4) . ? S4 C6 1.758(5) . ? S4 C8 1.776(5) . ? S5 C7 1.744(5) . ? S5 C9 1.819(5) . ? S6 C8 1.740(5) . ? S6 C14 1.816(4) . ? N1 C2 1.362(6) . ? N1 C1 1.367(5) . ? N1 C19 1.484(6) . ? C1 C3 1.356(7) . ? C2 C4 1.359(6) . ? C3 C4 1.397(6) . ? C5 C6 1.332(6) . ? C7 C8 1.353(6) . ? C9 C10 1.532(6) . ? C9 H9A 0.990 . ? C9 H9B 0.990 . ? C10 C11 1.509(7) . ? C10 H10A 0.990 . ? C10 H10B 0.990 . ? C11 C12 1.517(6) . ? C11 H11A 0.990 . ? C11 H11B 0.990 . ? C12 C13 1.507(8) . ? C12 H12A 0.990 . ? C12 H12B 0.990 . ? C13 H13A 0.980 . ? C13 H13B 0.980 . ? C13 H13C 0.980 . ? C14 C15 1.513(6) . ? C14 H14A 0.990 . ? C14 H14B 0.990 . ? C15 C16 1.507(6) . ? C15 H15A 0.990 . ? C15 H15B 0.990 . ? C16 C17 1.524(6) . ? C16 H16A 0.990 . ? C16 H16B 0.990 . ? C17 C18 1.529(6) . ? C17 H17A 0.990 . ? C17 H17B 0.990 . ? C18 H18A 0.980 . ? C18 H18B 0.980 . ? C18 H18C 0.980 . ? C19 H19A 0.980 . ? C19 H19B 0.980 . ? C19 H19C 0.980 . ? 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 C3 S1 C5 93.6(2) . . ? C4 S2 C5 93.4(2) . . ? C7 S3 C6 93.2(2) . . ? C6 S4 C8 93.5(2) . . ? C7 S5 C9 100.3(2) . . ? C8 S6 C14 101.1(2) . . ? C2 N1 C1 107.8(4) . . ? C2 N1 C19 125.9(4) . . ? C1 N1 C19 126.3(4) . . ? C3 C1 N1 108.5(4) . . ? C3 C1 Br1 127.9(4) . . ? N1 C1 Br1 123.7(4) . . ? C4 C2 N1 109.2(4) . . ? C4 C2 Br2 127.6(4) . . ? N1 C2 Br2 123.3(4) . . ? C1 C3 C4 107.8(4) . . ? C1 C3 S1 134.6(4) . . ? C4 C3 S1 117.3(4) . . ? C2 C4 C3 106.7(5) . . ? C2 C4 S2 135.2(4) . . ? C3 C4 S2 118.0(4) . . ? C6 C5 S1 121.7(4) . . ? C6 C5 S2 121.0(4) . . ? S1 C5 S2 117.3(3) . . ? C5 C6 S4 123.8(4) . . ? C5 C6 S3 124.0(4) . . ? S4 C6 S3 112.2(3) . . ? C8 C7 S5 124.6(4) . . ? C8 C7 S3 117.1(4) . . ? S5 C7 S3 117.9(3) . . ? C7 C8 S6 126.0(4) . . ? C7 C8 S4 115.6(4) . . ? S6 C8 S4 118.2(3) . . ? C10 C9 S5 114.0(3) . . ? C10 C9 H9A 108.7 . . ? S5 C9 H9A 108.7 . . ? C10 C9 H9B 108.7 . . ? S5 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C11 C10 C9 114.2(4) . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 115.1(4) . . ? C10 C11 H11A 108.5 . . ? C12 C11 H11A 108.5 . . ? C10 C11 H11B 108.5 . . ? C12 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C13 C12 C11 112.8(4) . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? C11 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 S6 113.3(3) . . ? C15 C14 H14A 108.9 . . ? S6 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? S6 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 111.8(4) . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15 C16 C17 113.5(4) . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16B 108.9 . . ? C17 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C16 C17 C18 113.0(4) . . ? C16 C17 H17A 109.0 . . ? C18 C17 H17A 109.0 . . ? C16 C17 H17B 109.0 . . ? C18 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 H19A 109.5 . . ? N1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C2 N1 C1 C3 -0.2(5) . . . . ? C19 N1 C1 C3 178.5(4) . . . . ? C2 N1 C1 Br1 179.1(3) . . . . ? C19 N1 C1 Br1 -2.1(6) . . . . ? C1 N1 C2 C4 -0.2(5) . . . . ? C19 N1 C2 C4 -179.0(4) . . . . ? C1 N1 C2 Br2 -178.6(3) . . . . ? C19 N1 C2 Br2 2.6(7) . . . . ? N1 C1 C3 C4 0.6(5) . . . . ? Br1 C1 C3 C4 -178.8(3) . . . . ? N1 C1 C3 S1 175.1(4) . . . . ? Br1 C1 C3 S1 -4.2(8) . . . . ? C5 S1 C3 C1 -178.3(5) . . . . ? C5 S1 C3 C4 -4.2(4) . . . . ? N1 C2 C4 C3 0.6(5) . . . . ? Br2 C2 C4 C3 178.9(3) . . . . ? N1 C2 C4 S2 -175.9(4) . . . . ? Br2 C2 C4 S2 2.4(8) . . . . ? C1 C3 C4 C2 -0.7(5) . . . . ? S1 C3 C4 C2 -176.3(3) . . . . ? C1 C3 C4 S2 176.5(3) . . . . ? S1 C3 C4 S2 0.9(5) . . . . ? C5 S2 C4 C2 179.1(5) . . . . ? C5 S2 C4 C3 2.9(4) . . . . ? C3 S1 C5 C6 -174.5(4) . . . . ? C3 S1 C5 S2 6.3(3) . . . . ? C4 S2 C5 C6 174.8(4) . . . . ? C4 S2 C5 S1 -5.9(3) . . . . ? S1 C5 C6 S4 179.6(2) . . . . ? S2 C5 C6 S4 -1.1(6) . . . . ? S1 C5 C6 S3 2.3(6) . . . . ? S2 C5 C6 S3 -178.5(2) . . . . ? C8 S4 C6 C5 -149.9(4) . . . . ? C8 S4 C6 S3 27.7(3) . . . . ? C7 S3 C6 C5 149.4(4) . . . . ? C7 S3 C6 S4 -28.2(3) . . . . ? C9 S5 C7 C8 -127.0(4) . . . . ? C9 S5 C7 S3 60.4(3) . . . . ? C6 S3 C7 C8 17.9(4) . . . . ? C6 S3 C7 S5 -169.0(3) . . . . ? S5 C7 C8 S6 0.3(6) . . . . ? S3 C7 C8 S6 172.9(2) . . . . ? S5 C7 C8 S4 -173.9(2) . . . . ? S3 C7 C8 S4 -1.2(5) . . . . ? C14 S6 C8 C7 135.3(4) . . . . ? C14 S6 C8 S4 -50.6(3) . . . . ? C6 S4 C8 C7 -16.1(4) . . . . ? C6 S4 C8 S6 169.3(3) . . . . ? C7 S5 C9 C10 67.2(4) . . . . ? S5 C9 C10 C11 58.9(5) . . . . ? C9 C10 C11 C12 174.8(4) . . . . ? C10 C11 C12 C13 179.5(4) . . . . ? C8 S6 C14 C15 -64.3(4) . . . . ? S6 C14 C15 C16 179.4(4) . . . . ? C14 C15 C16 C17 177.0(4) . . . . ? C15 C16 C17 C18 -179.9(4) . . . . ? #============================================================================= data_3b _database_code_depnum_ccdc_archive 'CCDC 649632' _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H25 I2 N S6' _chemical_formula_sum 'C19 H25 I2 N S6' _chemical_formula_weight 713.56 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' I I -0.4742 1.8119 '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 17.7967(6) _cell_length_b 7.9872(3) _cell_length_c 18.2265(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.503(1) _cell_angle_gamma 90.00 _cell_volume 2585.98(16) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9689 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 24.23 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.833 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 2.924 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.816 _exptl_absorpt_correction_T_max 0.944 _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.864574 ; _exptl_special_details ? _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 42034 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 26.37 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 5251 _reflns_number_gt 3729 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-22 (Bruker-Nonius, 2004)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a (Bruker, 2003)' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL v.6.10 (Sheldrick, 2000)' _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^)+(0.0438P)^2^] 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 5251 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0687 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.615 _refine_diff_density_min -0.792 _refine_diff_density_rms 0.118 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 I1 I 0.325710(15) 0.87802(4) 0.392951(14) 0.03229(10) Uani 1 1 d . . . I2 I 0.491375(16) 0.83165(4) 0.696857(14) 0.03728(10) Uani 1 1 d . . . S1 S 0.52128(6) 0.67028(14) 0.39164(5) 0.0304(3) Uani 1 1 d . . . S2 S 0.60374(6) 0.65017(13) 0.54087(5) 0.0295(3) Uani 1 1 d . . . S3 S 0.66630(6) 0.51996(14) 0.31839(5) 0.0325(3) Uani 1 1 d . . . S4 S 0.74805(6) 0.49435(13) 0.46174(5) 0.0294(2) Uani 1 1 d . . . S5 S 0.80495(6) 0.57176(13) 0.23534(5) 0.0294(2) Uani 1 1 d . . . S6 S 0.90066(6) 0.53350(13) 0.39997(6) 0.0304(3) Uani 1 1 d . . . N1 N 0.40421(17) 0.8670(4) 0.54796(16) 0.0251(8) Uani 1 1 d . . . C1 C 0.4095(2) 0.8297(5) 0.4737(2) 0.0256(9) Uani 1 1 d . . . C2 C 0.4704(2) 0.8147(5) 0.5849(2) 0.0270(10) Uani 1 1 d . . . C3 C 0.4777(2) 0.7583(5) 0.46555(19) 0.0236(9) Uani 1 1 d . . . C4 C 0.5161(2) 0.7479(5) 0.53494(19) 0.0248(9) Uani 1 1 d . . . C5 C 0.6043(2) 0.6156(5) 0.4448(2) 0.0245(9) Uani 1 1 d . . . C6 C 0.6631(2) 0.5522(5) 0.4136(2) 0.0256(9) Uani 1 1 d . . . C7 C 0.7648(2) 0.5485(5) 0.3200(2) 0.0255(9) Uani 1 1 d . . . C8 C 0.8028(2) 0.5345(5) 0.3859(2) 0.0252(9) Uani 1 1 d . . . C9 C 0.7585(3) 0.7622(5) 0.2010(2) 0.0373(11) Uani 1 1 d . . . H9A H 0.7717 0.7809 0.1496 0.045 Uiso 1 1 calc R . . H9B H 0.7033 0.7459 0.2005 0.045 Uiso 1 1 calc R . . C10 C 0.7795(3) 0.9183(5) 0.2461(2) 0.0392(11) Uani 1 1 d . . . H10A H 0.7511 1.0149 0.2246 0.047 Uiso 1 1 calc R . . H10B H 0.7636 0.9020 0.2967 0.047 Uiso 1 1 calc R . . C11 C 0.8621(2) 0.9595(5) 0.2498(2) 0.0353(10) Uani 1 1 d . . . H11A H 0.8792 0.9630 0.1992 0.042 Uiso 1 1 calc R . . H11B H 0.8899 0.8681 0.2763 0.042 Uiso 1 1 calc R . . C12 C 0.8827(3) 1.1244(5) 0.2876(2) 0.0414(12) Uani 1 1 d . . . H12A H 0.8556 1.2167 0.2610 0.050 Uiso 1 1 calc R . . H12B H 0.8659 1.1219 0.3384 0.050 Uiso 1 1 calc R . . C13 C 0.9663(3) 1.1589(6) 0.2902(3) 0.0507(13) Uani 1 1 d . . . H13A H 0.9769 1.2652 0.3156 0.076 Uiso 1 1 calc R . . H13B H 0.9829 1.1655 0.2400 0.076 Uiso 1 1 calc R . . H13C H 0.9933 1.0682 0.3167 0.076 Uiso 1 1 calc R . . C14 C 0.9138(2) 0.6679(5) 0.4795(2) 0.0278(10) Uani 1 1 d . . . H14A H 0.8852 0.6211 0.5197 0.033 Uiso 1 1 calc R . . H14B H 0.9678 0.6674 0.4963 0.033 Uiso 1 1 calc R . . C15 C 0.8891(2) 0.8475(5) 0.4658(2) 0.0292(10) Uani 1 1 d . . . H15A H 0.9180 0.8954 0.4262 0.035 Uiso 1 1 calc R . . H15B H 0.8351 0.8487 0.4489 0.035 Uiso 1 1 calc R . . C16 C 0.9004(2) 0.9560(5) 0.5339(2) 0.0307(10) Uani 1 1 d . . . H16A H 0.8689 0.9114 0.5724 0.037 Uiso 1 1 calc R . . H16B H 0.9537 0.9477 0.5527 0.037 Uiso 1 1 calc R . . C17 C 0.8811(2) 1.1378(5) 0.5213(2) 0.0318(10) Uani 1 1 d . . . H17A H 0.8276 1.1465 0.5035 0.038 Uiso 1 1 calc R . . H17B H 0.9120 1.1822 0.4823 0.038 Uiso 1 1 calc R . . C18 C 0.8940(3) 1.2451(6) 0.5897(2) 0.0398(11) Uani 1 1 d . . . H18A H 0.8801 1.3612 0.5780 0.060 Uiso 1 1 calc R . . H18B H 0.9472 1.2402 0.6068 0.060 Uiso 1 1 calc R . . H18C H 0.8630 1.2031 0.6283 0.060 Uiso 1 1 calc R . . C19 C 0.3409(2) 0.9479(5) 0.5808(2) 0.0325(10) Uani 1 1 d . . . H19A H 0.3129 1.0155 0.5435 0.049 Uiso 1 1 calc R . . H19B H 0.3597 1.0202 0.6213 0.049 Uiso 1 1 calc R . . H19C H 0.3076 0.8623 0.5995 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 I1 0.02996(17) 0.04251(19) 0.02402(15) 0.00471(13) -0.00156(11) 0.00156(13) I2 0.0452(2) 0.0499(2) 0.01664(15) -0.00410(12) 0.00055(12) -0.00845(14) S1 0.0289(6) 0.0462(7) 0.0160(5) -0.0010(5) 0.0006(4) 0.0040(5) S2 0.0302(6) 0.0410(7) 0.0168(5) 0.0016(4) -0.0014(4) 0.0023(5) S3 0.0268(6) 0.0470(7) 0.0233(5) -0.0054(5) -0.0008(4) -0.0023(5) S4 0.0281(6) 0.0362(6) 0.0238(5) 0.0049(5) 0.0011(4) 0.0004(5) S5 0.0352(6) 0.0310(6) 0.0224(5) -0.0029(4) 0.0053(4) 0.0016(5) S6 0.0263(6) 0.0323(6) 0.0325(6) -0.0029(5) 0.0012(5) 0.0016(5) N1 0.029(2) 0.0244(19) 0.0226(18) -0.0028(14) 0.0052(15) -0.0015(15) C1 0.029(2) 0.028(2) 0.019(2) 0.0009(17) -0.0012(18) -0.0074(18) C2 0.035(3) 0.030(2) 0.016(2) 0.0019(17) -0.0003(18) -0.0056(19) C3 0.028(2) 0.026(2) 0.017(2) 0.0007(17) 0.0010(17) -0.0019(18) C4 0.028(2) 0.030(2) 0.016(2) 0.0021(18) 0.0014(17) -0.0045(18) C5 0.026(2) 0.028(2) 0.019(2) 0.0039(17) -0.0015(17) -0.0042(18) C6 0.027(2) 0.027(2) 0.022(2) 0.0015(18) 0.0018(17) -0.0032(18) C7 0.025(2) 0.023(2) 0.029(2) -0.0013(18) 0.0058(18) 0.0003(17) C8 0.030(2) 0.023(2) 0.023(2) -0.0008(17) 0.0037(18) 0.0012(18) C9 0.042(3) 0.040(3) 0.029(2) 0.003(2) -0.001(2) 0.002(2) C10 0.052(3) 0.033(3) 0.033(3) 0.002(2) 0.003(2) 0.009(2) C11 0.047(3) 0.030(3) 0.029(2) -0.0009(19) 0.005(2) 0.003(2) C12 0.070(4) 0.028(3) 0.026(2) 0.001(2) 0.001(2) -0.002(2) C13 0.069(4) 0.043(3) 0.040(3) -0.005(2) 0.001(3) -0.010(3) C14 0.028(2) 0.029(2) 0.025(2) 0.0044(18) -0.0029(18) -0.0027(18) C15 0.031(2) 0.030(3) 0.025(2) 0.0030(18) -0.0053(18) -0.0028(18) C16 0.036(3) 0.032(3) 0.024(2) 0.0002(19) 0.0028(18) -0.002(2) C17 0.036(2) 0.033(3) 0.027(2) -0.0023(19) 0.0033(19) -0.0017(19) C18 0.053(3) 0.032(3) 0.034(3) -0.001(2) 0.005(2) -0.005(2) C19 0.036(3) 0.037(3) 0.026(2) -0.005(2) 0.0067(19) 0.003(2) _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 I1 C1 2.067(4) . ? I2 C2 2.056(4) . ? S1 C3 1.743(4) . ? S1 C5 1.771(4) . ? S2 C4 1.741(4) . ? S2 C5 1.773(4) . ? S3 C6 1.759(4) . ? S3 C7 1.767(4) . ? S4 C6 1.763(4) . ? S4 C8 1.769(4) . ? S5 C7 1.750(4) . ? S5 C9 1.823(4) . ? S6 C8 1.745(4) . ? S6 C14 1.808(4) . ? N1 C2 1.385(5) . ? N1 C1 1.394(5) . ? N1 C19 1.459(5) . ? C1 C3 1.357(5) . ? C2 C4 1.367(5) . ? C3 C4 1.403(5) . ? C5 C6 1.322(5) . ? C7 C8 1.345(5) . ? C9 C10 1.527(6) . ? C9 H9A 0.990 . ? C9 H9B 0.990 . ? C10 C11 1.504(6) . ? C10 H10A 0.990 . ? C10 H10B 0.990 . ? C11 C12 1.520(6) . ? C11 H11A 0.990 . ? C11 H11B 0.990 . ? C12 C13 1.512(7) . ? C12 H12A 0.990 . ? C12 H12B 0.990 . ? C13 H13A 0.980 . ? C13 H13B 0.980 . ? C13 H13C 0.980 . ? C14 C15 1.517(5) . ? C14 H14A 0.990 . ? C14 H14B 0.990 . ? C15 C16 1.517(5) . ? C15 H15A 0.990 . ? C15 H15B 0.990 . ? C16 C17 1.507(6) . ? C16 H16A 0.990 . ? C16 H16B 0.990 . ? C17 C18 1.518(6) . ? C17 H17A 0.990 . ? C17 H17B 0.990 . ? C18 H18A 0.980 . ? C18 H18B 0.980 . ? C18 H18C 0.980 . ? C19 H19A 0.980 . ? C19 H19B 0.980 . ? C19 H19C 0.980 . ? 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 C3 S1 C5 94.12(18) . . ? C4 S2 C5 93.85(18) . . ? C6 S3 C7 93.25(18) . . ? C6 S4 C8 93.44(18) . . ? C7 S5 C9 101.00(19) . . ? C8 S6 C14 101.23(19) . . ? C2 N1 C1 107.6(3) . . ? C2 N1 C19 126.1(3) . . ? C1 N1 C19 126.3(3) . . ? C3 C1 N1 108.1(3) . . ? C3 C1 I1 127.7(3) . . ? N1 C1 I1 124.2(3) . . ? C4 C2 N1 108.5(3) . . ? C4 C2 I2 127.4(3) . . ? N1 C2 I2 124.1(3) . . ? C1 C3 C4 108.4(3) . . ? C1 C3 S1 134.2(3) . . ? C4 C3 S1 117.2(3) . . ? C2 C4 C3 107.5(3) . . ? C2 C4 S2 134.5(3) . . ? C3 C4 S2 117.9(3) . . ? C6 C5 S1 120.9(3) . . ? C6 C5 S2 122.5(3) . . ? S1 C5 S2 116.6(2) . . ? C5 C6 S3 123.8(3) . . ? C5 C6 S4 124.3(3) . . ? S3 C6 S4 112.0(2) . . ? C8 C7 S5 125.9(3) . . ? C8 C7 S3 116.6(3) . . ? S5 C7 S3 117.2(2) . . ? C7 C8 S6 125.0(3) . . ? C7 C8 S4 116.2(3) . . ? S6 C8 S4 118.5(2) . . ? C10 C9 S5 113.9(3) . . ? C10 C9 H9A 108.8 . . ? S5 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? S5 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C9 114.2(4) . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 114.7(4) . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C13 C12 C11 112.4(4) . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 S6 114.0(3) . . ? C15 C14 H14A 108.7 . . ? S6 C14 H14A 108.7 . . ? C15 C14 H14B 108.7 . . ? S6 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? C16 C15 C14 112.5(3) . . ? C16 C15 H15A 109.1 . . ? C14 C15 H15A 109.1 . . ? C16 C15 H15B 109.1 . . ? C14 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? C17 C16 C15 114.1(3) . . ? C17 C16 H16A 108.7 . . ? C15 C16 H16A 108.7 . . ? C17 C16 H16B 108.7 . . ? C15 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C16 C17 C18 113.4(3) . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17A 108.9 . . ? C16 C17 H17B 108.9 . . ? C18 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 H19A 109.5 . . ? N1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C2 N1 C1 C3 -0.7(4) . . . . ? C19 N1 C1 C3 178.7(4) . . . . ? C2 N1 C1 I1 179.2(3) . . . . ? C19 N1 C1 I1 -1.4(5) . . . . ? C1 N1 C2 C4 0.5(4) . . . . ? C19 N1 C2 C4 -178.9(4) . . . . ? C1 N1 C2 I2 -177.7(3) . . . . ? C19 N1 C2 I2 2.9(5) . . . . ? N1 C1 C3 C4 0.6(4) . . . . ? I1 C1 C3 C4 -179.3(3) . . . . ? N1 C1 C3 S1 175.8(3) . . . . ? I1 C1 C3 S1 -4.1(6) . . . . ? C5 S1 C3 C1 -178.4(4) . . . . ? C5 S1 C3 C4 -3.7(3) . . . . ? N1 C2 C4 C3 -0.1(4) . . . . ? I2 C2 C4 C3 178.0(3) . . . . ? N1 C2 C4 S2 -176.3(3) . . . . ? I2 C2 C4 S2 1.8(6) . . . . ? C1 C3 C4 C2 -0.3(4) . . . . ? S1 C3 C4 C2 -176.4(3) . . . . ? C1 C3 C4 S2 176.6(3) . . . . ? S1 C3 C4 S2 0.6(4) . . . . ? C5 S2 C4 C2 178.8(4) . . . . ? C5 S2 C4 C3 2.9(3) . . . . ? C3 S1 C5 C6 -174.5(4) . . . . ? C3 S1 C5 S2 5.6(2) . . . . ? C4 S2 C5 C6 174.7(4) . . . . ? C4 S2 C5 S1 -5.4(2) . . . . ? S1 C5 C6 S3 1.4(5) . . . . ? S2 C5 C6 S3 -178.7(2) . . . . ? S1 C5 C6 S4 179.9(2) . . . . ? S2 C5 C6 S4 -0.2(5) . . . . ? C7 S3 C6 C5 150.5(4) . . . . ? C7 S3 C6 S4 -28.2(2) . . . . ? C8 S4 C6 C5 -151.0(4) . . . . ? C8 S4 C6 S3 27.6(2) . . . . ? C9 S5 C7 C8 -125.0(4) . . . . ? C9 S5 C7 S3 61.7(3) . . . . ? C6 S3 C7 C8 18.1(3) . . . . ? C6 S3 C7 S5 -168.0(2) . . . . ? S5 C7 C8 S6 -1.0(6) . . . . ? S3 C7 C8 S6 172.3(2) . . . . ? S5 C7 C8 S4 -174.8(2) . . . . ? S3 C7 C8 S4 -1.5(4) . . . . ? C14 S6 C8 C7 137.0(4) . . . . ? C14 S6 C8 S4 -49.3(3) . . . . ? C6 S4 C8 C7 -15.9(3) . . . . ? C6 S4 C8 S6 169.9(2) . . . . ? C7 S5 C9 C10 65.9(3) . . . . ? S5 C9 C10 C11 59.8(4) . . . . ? C9 C10 C11 C12 173.8(4) . . . . ? C10 C11 C12 C13 179.6(4) . . . . ? C8 S6 C14 C15 -64.5(3) . . . . ? S6 C14 C15 C16 179.6(3) . . . . ? C14 C15 C16 C17 176.3(4) . . . . ? C15 C16 C17 C18 -179.0(4) . . . . ? #============================================================================= data_4a _database_code_depnum_ccdc_archive 'CCDC 649633' _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H50 Br4 N2 S12' _chemical_formula_sum 'C38 H50 Br4 N2 S12' _chemical_formula_weight 1239.16 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.6042(6) _cell_length_b 14.9350(8) _cell_length_c 16.0311(9) _cell_angle_alpha 112.535(2) _cell_angle_beta 90.490(2) _cell_angle_gamma 106.707(2) _cell_volume 2435.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3042 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 20.31 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.690 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 3.850 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.470 _exptl_absorpt_correction_T_max 0.927 _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.507206 ; _exptl_special_details ; One pentyl chain is modelled as disordered over two orientations: * The S12---C34 and S12---C34A distances were restrained to a common refined value. * All C---C distances along the disordered chains were restrained to a common refined value, and the 1,3-distances were restrained to 1.633 times that value. * The site occupancy factors were refined, with all atoms of a given chain component constrained to have the same occupancy, with the sum of the occupancies of the two components constrained to be unity, and with all atoms having constrained Uiso values of 0.05 \%A^2^. The resulting refined site occupancies were then fixed to 0.65:0.35, and each atom was refined with its own Uiso value. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 25427 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_av_sigmaI/netI 0.1236 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 24.71 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.983 _reflns_number_total 8168 _reflns_number_gt 4520 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-22 (Bruker-Nonius, 2004)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a (Bruker, 2003)' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL v.6.10 (Sheldrick, 2000)' _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^)+(0.0451P)^2^] 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 8168 _refine_ls_number_parameters 507 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.1229 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1128 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.618 _refine_diff_density_min -0.647 _refine_diff_density_rms 0.119 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 0.04499(7) 0.59429(6) 0.66967(5) 0.0408(2) Uani 1 1 d . . . Br2 Br 0.32146(7) 0.40790(6) 0.40847(5) 0.0410(2) Uani 1 1 d . . . Br3 Br 0.35897(7) 1.09519(6) 0.59096(5) 0.0403(2) Uani 1 1 d . . . Br4 Br 0.34167(8) 0.81055(6) 0.23117(5) 0.0430(2) Uani 1 1 d . . . S1 S 0.27865(17) 0.79338(14) 0.63684(12) 0.0338(5) Uani 1 1 d . . . S2 S 0.43141(16) 0.67810(13) 0.46537(11) 0.0290(4) Uani 1 1 d . . . S3 S 0.17580(17) 0.84679(14) 0.57224(12) 0.0343(5) Uani 1 1 d . . . S4 S 0.16974(16) 0.67377(13) 0.35647(12) 0.0295(4) Uani 1 1 d . . . S5 S 0.08881(16) 0.51733(14) 0.15751(12) 0.0328(5) Uani 1 1 d . . . S6 S 0.24942(16) 0.40692(13) 0.18135(12) 0.0312(5) Uani 1 1 d . . . S7 S -0.04870(18) 0.34596(16) -0.01759(12) 0.0421(5) Uani 1 1 d . . . S8 S 0.11378(18) 0.21031(14) 0.02763(13) 0.0402(5) Uani 1 1 d . . . S9 S 0.46988(16) 0.58589(14) 0.17819(11) 0.0306(5) Uani 1 1 d . A . S10 S 0.62813(16) 0.62931(14) 0.34147(11) 0.0297(4) Uani 1 1 d . . . S11 S 0.67038(17) 0.59452(15) 0.06259(12) 0.0354(5) Uani 1 1 d . A . S12 S 0.85183(17) 0.63452(16) 0.24812(13) 0.0393(5) Uani 1 1 d D . . N1 N 0.1738(5) 0.4922(4) 0.5354(4) 0.0282(14) Uani 1 1 d . . . N2 N 0.3618(5) 0.9592(4) 0.4109(4) 0.0307(14) Uani 1 1 d . . . C1 C 0.1606(6) 0.5858(5) 0.5901(4) 0.0261(17) Uani 1 1 d . . . C2 C 0.2427(6) 0.6616(5) 0.5734(4) 0.0273(17) Uani 1 1 d . . . C3 C 0.3116(6) 0.6149(5) 0.5064(4) 0.0235(16) Uani 1 1 d . . . C4 C 0.2686(6) 0.5123(5) 0.4865(4) 0.0256(17) Uani 1 1 d . . . C5 C 0.1003(7) 0.3923(6) 0.5308(5) 0.042(2) Uani 1 1 d . . . H5A H 0.1328 0.3395 0.4910 0.064 Uiso 1 1 calc R . . H5B H 0.0162 0.3778 0.5063 0.064 Uiso 1 1 calc R . . H5C H 0.1026 0.3926 0.5920 0.064 Uiso 1 1 calc R . . C6 C 0.3234(6) 0.9665(5) 0.4934(4) 0.0285(17) Uani 1 1 d . . . C7 C 0.2578(6) 0.8739(5) 0.4889(4) 0.0262(17) Uani 1 1 d . . . C8 C 0.2545(5) 0.8027(5) 0.3979(4) 0.0249(17) Uani 1 1 d . . . C9 C 0.3167(6) 0.8577(6) 0.3536(5) 0.0314(18) Uani 1 1 d . . . C10 C 0.4333(6) 1.0431(5) 0.3869(5) 0.039(2) Uani 1 1 d . . . H10A H 0.4785 1.0163 0.3368 0.059 Uiso 1 1 calc R . . H10B H 0.4905 1.0957 0.4400 0.059 Uiso 1 1 calc R . . H10C H 0.3785 1.0729 0.3678 0.059 Uiso 1 1 calc R . . C11 C 0.2654(6) 0.6020(5) 0.3039(4) 0.0209(16) Uani 1 1 d . . . C12 C 0.2111(6) 0.5196(5) 0.2253(4) 0.0250(17) Uani 1 1 d . . . C13 C 0.0597(6) 0.3920(5) 0.0777(4) 0.0315(18) Uani 1 1 d . . . C14 C 0.1292(6) 0.3387(5) 0.0915(4) 0.0279(17) Uani 1 1 d . . . C15 C 0.3881(6) 0.6234(5) 0.3462(4) 0.0246(16) Uani 1 1 d . . . C16 C 0.4825(6) 0.6145(5) 0.2956(4) 0.0257(16) Uani 1 1 d . . . C17 C 0.6259(6) 0.6082(5) 0.1705(5) 0.0289(18) Uani 1 1 d . . . C18 C 0.6981(6) 0.6273(5) 0.2447(5) 0.0258(17) Uani 1 1 d . A . C19 C -0.1785(6) 0.3785(6) 0.0345(5) 0.037(2) Uani 1 1 d . . . H19A H -0.1519 0.4513 0.0773 0.044 Uiso 1 1 calc R . . H19B H -0.2405 0.3691 -0.0136 0.044 Uiso 1 1 calc R . . C20 C -0.2351(7) 0.3125(6) 0.0858(5) 0.045(2) Uani 1 1 d . . . H20A H -0.2759 0.2418 0.0411 0.055 Uiso 1 1 calc R . . H20B H -0.1696 0.3107 0.1246 0.055 Uiso 1 1 calc R . . C21 C -0.3266(7) 0.3507(6) 0.1454(5) 0.043(2) Uani 1 1 d . . . H21A H -0.2839 0.4184 0.1942 0.052 Uiso 1 1 calc R . . H21B H -0.3873 0.3595 0.1080 0.052 Uiso 1 1 calc R . . C22 C -0.3918(7) 0.2797(6) 0.1884(5) 0.048(2) Uani 1 1 d . . . H22A H -0.3310 0.2631 0.2184 0.058 Uiso 1 1 calc R . . H22B H -0.4437 0.2153 0.1397 0.058 Uiso 1 1 calc R . . C23 C -0.4708(8) 0.3239(7) 0.2584(5) 0.062(3) Uani 1 1 d . . . H23A H -0.5177 0.2714 0.2782 0.093 Uiso 1 1 calc R . . H23B H -0.5265 0.3465 0.2308 0.093 Uiso 1 1 calc R . . H23C H -0.4189 0.3822 0.3111 0.093 Uiso 1 1 calc R . . C24 C 0.0221(7) 0.1530(6) 0.0974(5) 0.049(2) Uani 1 1 d . . . H24A H -0.0483 0.1789 0.1088 0.059 Uiso 1 1 calc R . . H24B H -0.0101 0.0783 0.0615 0.059 Uiso 1 1 calc R . . C25 C 0.0854(8) 0.1719(7) 0.1882(5) 0.058(3) Uani 1 1 d . . . H25A H 0.0277 0.1332 0.2169 0.070 Uiso 1 1 calc R . . H25B H 0.1051 0.2454 0.2280 0.070 Uiso 1 1 calc R . . C26 C 0.2015(7) 0.1430(6) 0.1851(5) 0.051(2) Uani 1 1 d . . . H26A H 0.2616 0.1851 0.1605 0.062 Uiso 1 1 calc R . . H26B H 0.2355 0.1601 0.2482 0.062 Uiso 1 1 calc R . . C27 C 0.1854(9) 0.0333(7) 0.1292(6) 0.072(3) Uani 1 1 d . . . H27A H 0.1532 0.0164 0.0657 0.086 Uiso 1 1 calc R . . H27B H 0.1242 -0.0090 0.1530 0.086 Uiso 1 1 calc R . . C28 C 0.3015(10) 0.0052(8) 0.1283(7) 0.094(4) Uani 1 1 d . . . H28A H 0.2844 -0.0676 0.0901 0.141 Uiso 1 1 calc R . . H28B H 0.3327 0.0194 0.1906 0.141 Uiso 1 1 calc R . . H28C H 0.3622 0.0457 0.1037 0.141 Uiso 1 1 calc R . . C29 C 0.5923(7) 0.6712(5) 0.0348(4) 0.0340(19) Uani 1 1 d . . . H29A H 0.6071 0.6678 -0.0269 0.041 Uiso 1 1 calc R A . H29B H 0.5039 0.6409 0.0329 0.041 Uiso 1 1 calc R . . C30 C 0.6307(7) 0.7819(5) 0.1008(5) 0.038(2) Uani 1 1 d . A . H30A H 0.7202 0.8107 0.1074 0.046 Uiso 1 1 calc R . . H30B H 0.6083 0.7859 0.1613 0.046 Uiso 1 1 calc R . . C31 C 0.5735(8) 0.8462(6) 0.0713(5) 0.057(2) Uani 1 1 d . . . H31A H 0.5930 0.8391 0.0095 0.068 Uiso 1 1 calc R A . H31B H 0.4842 0.8184 0.0670 0.068 Uiso 1 1 calc R . . C32 C 0.6133(9) 0.9587(7) 0.1335(6) 0.072(3) Uani 1 1 d . A . H32A H 0.5639 0.9919 0.1122 0.087 Uiso 1 1 calc R . . H32B H 0.5959 0.9658 0.1956 0.087 Uiso 1 1 calc R . . C33 C 0.7404(9) 1.0126(8) 0.1384(6) 0.088(3) Uani 1 1 d . . . H33A H 0.7611 1.0817 0.1865 0.132 Uiso 1 1 calc R A . H33B H 0.7559 1.0168 0.0798 0.132 Uiso 1 1 calc R . . H33C H 0.7903 0.9758 0.1523 0.132 Uiso 1 1 calc R . . C34 C 0.9211(11) 0.7737(7) 0.3135(7) 0.042(3) Uiso 0.65 1 d PD A 1 H34A H 0.8737 0.7962 0.3642 0.051 Uiso 0.65 1 calc PR A 1 H34B H 1.0042 0.7866 0.3409 0.051 Uiso 0.65 1 calc PR A 1 C35 C 0.9289(10) 0.8393(7) 0.2597(7) 0.055(4) Uiso 0.65 1 d PD A 1 H35A H 0.9880 0.8259 0.2161 0.066 Uiso 0.65 1 calc PR A 1 H35B H 0.8487 0.8186 0.2240 0.066 Uiso 0.65 1 calc PR A 1 C36 C 0.9663(9) 0.9523(6) 0.3183(8) 0.066(4) Uiso 0.65 1 d PD A 1 H36A H 0.9484 0.9878 0.2812 0.079 Uiso 0.65 1 calc PR A 1 H36B H 0.9164 0.9640 0.3688 0.079 Uiso 0.65 1 calc PR A 1 C37 C 1.0985(9) 0.9995(8) 0.3582(8) 0.059(4) Uiso 0.65 1 d PD A 1 H37A H 1.1491 0.9834 0.3085 0.071 Uiso 0.65 1 calc PR A 1 H37B H 1.1154 0.9692 0.4003 0.071 Uiso 0.65 1 calc PR A 1 C38 C 1.1335(16) 1.1154(9) 0.4098(14) 0.075(9) Uiso 0.65 1 d PD A 1 H38A H 1.2196 1.1429 0.4351 0.112 Uiso 0.65 1 calc PR A 1 H38B H 1.0841 1.1317 0.4595 0.112 Uiso 0.65 1 calc PR A 1 H38C H 1.1191 1.1459 0.3680 0.112 Uiso 0.65 1 calc PR A 1 C34A C 0.9363(17) 0.7503(10) 0.2421(10) 0.036(5) Uiso 0.35 1 d PD A 2 H34C H 1.0177 0.7478 0.2255 0.043 Uiso 0.35 1 calc PR A 2 H34D H 0.8942 0.7623 0.1953 0.043 Uiso 0.35 1 calc PR A 2 C35A C 0.9483(17) 0.8361(10) 0.3361(10) 0.033(5) Uiso 0.35 1 d PD A 2 H35C H 0.9859 0.8217 0.3832 0.039 Uiso 0.35 1 calc PR A 2 H35D H 0.8669 0.8406 0.3510 0.039 Uiso 0.35 1 calc PR A 2 C36A C 1.027(2) 0.9374(9) 0.3351(10) 0.045(6) Uiso 0.35 1 d PD A 2 H36C H 1.1048 0.9296 0.3130 0.054 Uiso 0.35 1 calc PR A 2 H36D H 0.9852 0.9548 0.2923 0.054 Uiso 0.35 1 calc PR A 2 C37A C 1.0538(18) 1.0233(10) 0.4291(10) 0.047(6) Uiso 0.35 1 d PD A 2 H37C H 1.0921 1.0046 0.4727 0.056 Uiso 0.35 1 calc PR A 2 H37D H 0.9768 1.0339 0.4499 0.056 Uiso 0.35 1 calc PR A 2 C38A C 1.139(2) 1.1225(11) 0.4277(19) 0.029(10) Uiso 0.35 1 d PD A 2 H38D H 1.1535 1.1774 0.4887 0.044 Uiso 0.35 1 calc PR A 2 H38E H 1.1006 1.1409 0.3844 0.044 Uiso 0.35 1 calc PR A 2 H38F H 1.2157 1.1126 0.4090 0.044 Uiso 0.35 1 calc PR A 2 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 0.0383(5) 0.0481(5) 0.0405(5) 0.0234(4) 0.0188(4) 0.0121(4) Br2 0.0534(5) 0.0299(5) 0.0427(5) 0.0141(4) 0.0150(4) 0.0181(4) Br3 0.0415(5) 0.0216(4) 0.0488(5) 0.0067(4) 0.0046(4) 0.0073(4) Br4 0.0541(5) 0.0362(5) 0.0388(5) 0.0186(4) 0.0137(4) 0.0095(4) S1 0.0433(12) 0.0250(11) 0.0308(11) 0.0104(9) 0.0097(9) 0.0085(9) S2 0.0259(10) 0.0281(11) 0.0271(10) 0.0099(9) 0.0059(8) 0.0017(9) S3 0.0365(12) 0.0276(11) 0.0408(11) 0.0145(9) 0.0139(9) 0.0118(9) S4 0.0266(10) 0.0205(10) 0.0381(11) 0.0098(9) 0.0093(9) 0.0054(9) S5 0.0312(11) 0.0314(11) 0.0348(11) 0.0111(9) -0.0009(9) 0.0116(9) S6 0.0284(11) 0.0248(11) 0.0373(11) 0.0083(9) 0.0010(9) 0.0096(9) S7 0.0386(12) 0.0520(14) 0.0305(11) 0.0120(10) -0.0007(9) 0.0131(11) S8 0.0460(13) 0.0276(11) 0.0384(12) 0.0055(9) 0.0039(10) 0.0101(10) S9 0.0239(10) 0.0393(12) 0.0262(10) 0.0132(9) 0.0054(8) 0.0064(9) S10 0.0238(10) 0.0366(11) 0.0305(10) 0.0158(9) 0.0054(8) 0.0089(9) S11 0.0353(12) 0.0397(12) 0.0316(11) 0.0144(9) 0.0114(9) 0.0122(10) S12 0.0236(11) 0.0499(13) 0.0445(12) 0.0188(11) 0.0093(9) 0.0119(10) N1 0.034(4) 0.020(3) 0.031(3) 0.013(3) 0.005(3) 0.004(3) N2 0.025(3) 0.020(3) 0.047(4) 0.018(3) 0.009(3) 0.001(3) C1 0.021(4) 0.029(4) 0.027(4) 0.014(4) 0.006(3) 0.002(4) C2 0.029(4) 0.031(4) 0.023(4) 0.009(3) 0.002(3) 0.013(4) C3 0.021(4) 0.024(4) 0.024(4) 0.011(3) 0.007(3) 0.004(3) C4 0.034(4) 0.020(4) 0.023(4) 0.011(3) 0.010(3) 0.006(4) C5 0.041(5) 0.039(5) 0.048(5) 0.024(4) 0.004(4) 0.004(4) C6 0.033(4) 0.023(4) 0.026(4) 0.006(3) 0.007(3) 0.009(4) C7 0.026(4) 0.019(4) 0.030(4) 0.008(3) 0.004(3) 0.004(3) C8 0.012(4) 0.023(4) 0.036(4) 0.010(4) 0.000(3) 0.003(3) C9 0.026(4) 0.032(5) 0.036(4) 0.013(4) 0.009(4) 0.011(4) C10 0.028(4) 0.036(5) 0.063(5) 0.029(4) 0.011(4) 0.010(4) C11 0.023(4) 0.017(4) 0.027(4) 0.012(3) 0.010(3) 0.009(3) C12 0.022(4) 0.025(4) 0.026(4) 0.009(3) 0.005(3) 0.007(3) C13 0.028(4) 0.034(5) 0.025(4) 0.006(3) 0.005(3) 0.007(4) C14 0.030(4) 0.027(4) 0.022(4) 0.003(3) 0.008(3) 0.010(4) C15 0.026(4) 0.021(4) 0.025(4) 0.011(3) 0.002(3) 0.004(3) C16 0.022(4) 0.023(4) 0.031(4) 0.013(3) 0.004(3) 0.002(3) C17 0.022(4) 0.032(4) 0.037(4) 0.015(4) 0.010(4) 0.013(4) C18 0.014(4) 0.029(4) 0.034(4) 0.012(3) 0.011(3) 0.007(3) C19 0.025(4) 0.047(5) 0.041(5) 0.017(4) -0.003(4) 0.015(4) C20 0.034(5) 0.060(6) 0.035(5) 0.010(4) 0.000(4) 0.016(4) C21 0.037(5) 0.036(5) 0.055(5) 0.020(4) 0.002(4) 0.010(4) C22 0.052(5) 0.043(5) 0.045(5) 0.017(4) 0.005(4) 0.009(5) C23 0.053(6) 0.078(7) 0.063(6) 0.033(5) 0.021(5) 0.027(5) C24 0.044(5) 0.022(4) 0.069(6) 0.017(4) 0.000(5) -0.004(4) C25 0.067(7) 0.049(6) 0.050(6) 0.017(5) 0.008(5) 0.007(5) C26 0.046(5) 0.050(6) 0.052(5) 0.023(5) 0.002(4) 0.002(5) C27 0.088(8) 0.044(6) 0.067(7) 0.004(5) 0.005(6) 0.022(6) C28 0.102(9) 0.101(9) 0.101(8) 0.045(7) 0.011(7) 0.059(8) C29 0.040(5) 0.038(5) 0.026(4) 0.015(4) 0.007(4) 0.013(4) C30 0.043(5) 0.037(5) 0.035(4) 0.019(4) 0.012(4) 0.008(4) C31 0.070(6) 0.037(5) 0.061(6) 0.021(5) 0.008(5) 0.011(5) C32 0.077(7) 0.041(6) 0.079(7) 0.014(5) 0.030(6) 0.004(5) C33 0.090(8) 0.065(7) 0.081(7) 0.011(6) 0.037(6) 0.009(6) _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 C1 1.856(6) . ? Br2 C4 1.855(6) . ? Br3 C6 1.881(6) . ? Br4 C9 1.871(7) . ? S1 C2 1.751(7) . ? S1 S3 2.072(3) . ? S2 C3 1.730(7) . ? S2 C15 1.766(6) . ? S3 C7 1.752(7) . ? S4 C8 1.743(7) . ? S4 C11 1.760(6) . ? S5 C13 1.746(7) . ? S5 C12 1.765(7) . ? S6 C12 1.748(6) . ? S6 C14 1.755(7) . ? S7 C13 1.748(7) . ? S7 C19 1.826(7) . ? S8 C14 1.748(7) . ? S8 C24 1.829(8) . ? S9 C16 1.757(7) . ? S9 C17 1.759(7) . ? S10 C18 1.751(6) . ? S10 C16 1.756(7) . ? S11 C17 1.762(7) . ? S11 C29 1.819(7) . ? S12 C18 1.756(6) . ? S12 C34A 1.766(13) . ? S12 C34 1.850(10) . ? N1 C4 1.386(8) . ? N1 C1 1.391(8) . ? N1 C5 1.463(9) . ? N2 C9 1.372(8) . ? N2 C6 1.373(8) . ? N2 C10 1.479(8) . ? C1 C2 1.370(9) . ? C2 C3 1.429(8) . ? C3 C4 1.373(9) . ? C5 H5A 0.980 . ? C5 H5B 0.980 . ? C5 H5C 0.980 . ? C6 C7 1.347(9) . ? C7 C8 1.430(8) . ? C8 C9 1.347(9) . ? C10 H10A 0.980 . ? C10 H10B 0.980 . ? C10 H10C 0.980 . ? C11 C12 1.360(8) . ? C11 C15 1.465(8) . ? C13 C14 1.353(9) . ? C15 C16 1.375(8) . ? C17 C18 1.335(9) . ? C19 C20 1.529(10) . ? C19 H19A 0.990 . ? C19 H19B 0.990 . ? C20 C21 1.521(9) . ? C20 H20A 0.990 . ? C20 H20B 0.990 . ? C21 C22 1.509(10) . ? C21 H21A 0.990 . ? C21 H21B 0.990 . ? C22 C23 1.528(9) . ? C22 H22A 0.990 . ? C22 H22B 0.990 . ? C23 H23A 0.980 . ? C23 H23B 0.980 . ? C23 H23C 0.980 . ? C24 C25 1.512(10) . ? C24 H24A 0.990 . ? C24 H24B 0.990 . ? C25 C26 1.524(10) . ? C25 H25A 0.990 . ? C25 H25B 0.990 . ? C26 C27 1.490(10) . ? C26 H26A 0.990 . ? C26 H26B 0.990 . ? C27 C28 1.520(11) . ? C27 H27A 0.990 . ? C27 H27B 0.990 . ? C28 H28A 0.980 . ? C28 H28B 0.980 . ? C28 H28C 0.980 . ? C29 C30 1.510(9) . ? C29 H29A 0.990 . ? C29 H29B 0.990 . ? C30 C31 1.515(10) . ? C30 H30A 0.990 . ? C30 H30B 0.990 . ? C31 C32 1.514(10) . ? C31 H31A 0.990 . ? C31 H31B 0.990 . ? C32 C33 1.448(12) . ? C32 H32A 0.990 . ? C32 H32B 0.990 . ? C33 H33A 0.980 . ? C33 H33B 0.980 . ? C33 H33C 0.980 . ? C34 C35 1.519(9) . ? C34 H34A 0.990 . ? C34 H34B 0.990 . ? C35 C36 1.509(9) . ? C35 H35A 0.990 . ? C35 H35B 0.990 . ? C36 C37 1.508(10) . ? C36 H36A 0.990 . ? C36 H36B 0.990 . ? C37 C38 1.529(9) . ? C37 H37A 0.990 . ? C37 H37B 0.990 . ? C38 H38A 0.980 . ? C38 H38B 0.980 . ? C38 H38C 0.980 . ? C34A C35A 1.532(10) . ? C34A H34C 0.990 . ? C34A H34D 0.990 . ? C35A C36A 1.533(10) . ? C35A H35C 0.990 . ? C35A H35D 0.990 . ? C36A C37A 1.516(10) . ? C36A H36C 0.990 . ? C36A H36D 0.990 . ? C37A C38A 1.533(11) . ? C37A H37C 0.990 . ? C37A H37D 0.990 . ? C38A H38D 0.980 . ? C38A H38E 0.980 . ? C38A H38F 0.980 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 S3 107.4(2) . . ? C3 S2 C15 104.3(3) . . ? C7 S3 S1 106.9(2) . . ? C8 S4 C11 108.0(3) . . ? C13 S5 C12 96.6(3) . . ? C12 S6 C14 96.7(3) . . ? C13 S7 C19 101.9(3) . . ? C14 S8 C24 99.6(3) . . ? C16 S9 C17 95.8(3) . . ? C18 S10 C16 96.4(3) . . ? C17 S11 C29 100.0(3) . . ? C18 S12 C34A 108.5(7) . . ? C18 S12 C34 99.2(4) . . ? C4 N1 C1 106.7(6) . . ? C4 N1 C5 127.2(6) . . ? C1 N1 C5 126.0(6) . . ? C9 N2 C6 105.9(6) . . ? C9 N2 C10 126.5(6) . . ? C6 N2 C10 127.6(6) . . ? C2 C1 N1 109.1(6) . . ? C2 C1 Br1 129.8(5) . . ? N1 C1 Br1 121.0(5) . . ? C1 C2 C3 107.7(6) . . ? C1 C2 S1 126.6(5) . . ? C3 C2 S1 124.6(5) . . ? C4 C3 C2 106.1(6) . . ? C4 C3 S2 127.8(5) . . ? C2 C3 S2 126.0(5) . . ? C3 C4 N1 110.2(5) . . ? C3 C4 Br2 128.9(5) . . ? N1 C4 Br2 120.9(5) . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 N2 110.6(6) . . ? C7 C6 Br3 129.4(5) . . ? N2 C6 Br3 120.0(5) . . ? C6 C7 C8 106.5(6) . . ? C6 C7 S3 127.1(5) . . ? C8 C7 S3 125.9(5) . . ? C9 C8 C7 106.4(6) . . ? C9 C8 S4 129.8(5) . . ? C7 C8 S4 123.4(5) . . ? C8 C9 N2 110.6(6) . . ? C8 C9 Br4 127.8(6) . . ? N2 C9 Br4 121.6(6) . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C15 123.1(5) . . ? C12 C11 S4 114.0(5) . . ? C15 C11 S4 122.6(5) . . ? C11 C12 S6 125.7(5) . . ? C11 C12 S5 121.3(5) . . ? S6 C12 S5 113.0(4) . . ? C14 C13 S5 116.9(5) . . ? C14 C13 S7 124.2(5) . . ? S5 C13 S7 118.8(4) . . ? C13 C14 S8 126.8(5) . . ? C13 C14 S6 116.4(5) . . ? S8 C14 S6 116.8(4) . . ? C16 C15 C11 121.7(6) . . ? C16 C15 S2 114.6(5) . . ? C11 C15 S2 123.2(5) . . ? C15 C16 S10 123.4(5) . . ? C15 C16 S9 123.7(5) . . ? S10 C16 S9 112.9(4) . . ? C18 C17 S9 117.4(5) . . ? C18 C17 S11 126.1(5) . . ? S9 C17 S11 116.3(4) . . ? C17 C18 S10 116.6(5) . . ? C17 C18 S12 125.0(5) . . ? S10 C18 S12 117.9(4) . . ? C20 C19 S7 111.8(5) . . ? C20 C19 H19A 109.2 . . ? S7 C19 H19A 109.2 . . ? C20 C19 H19B 109.2 . . ? S7 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C21 C20 C19 113.4(6) . . ? C21 C20 H20A 108.9 . . ? C19 C20 H20A 108.9 . . ? C21 C20 H20B 108.9 . . ? C19 C20 H20B 108.9 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C20 113.3(6) . . ? C22 C21 H21A 108.9 . . ? C20 C21 H21A 108.9 . . ? C22 C21 H21B 108.9 . . ? C20 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C21 C22 C23 113.7(6) . . ? C21 C22 H22A 108.8 . . ? C23 C22 H22A 108.8 . . ? C21 C22 H22B 108.8 . . ? C23 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 S8 116.5(6) . . ? C25 C24 H24A 108.2 . . ? S8 C24 H24A 108.2 . . ? C25 C24 H24B 108.2 . . ? S8 C24 H24B 108.2 . . ? H24A C24 H24B 107.3 . . ? C24 C25 C26 116.0(7) . . ? C24 C25 H25A 108.3 . . ? C26 C25 H25A 108.3 . . ? C24 C25 H25B 108.3 . . ? C26 C25 H25B 108.3 . . ? H25A C25 H25B 107.4 . . ? C27 C26 C25 114.5(7) . . ? C27 C26 H26A 108.6 . . ? C25 C26 H26A 108.6 . . ? C27 C26 H26B 108.6 . . ? C25 C26 H26B 108.6 . . ? H26A C26 H26B 107.6 . . ? C26 C27 C28 113.9(8) . . ? C26 C27 H27A 108.8 . . ? C28 C27 H27A 108.8 . . ? C26 C27 H27B 108.8 . . ? C28 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 S11 114.3(5) . . ? C30 C29 H29A 108.7 . . ? S11 C29 H29A 108.7 . . ? C30 C29 H29B 108.7 . . ? S11 C29 H29B 108.7 . . ? H29A C29 H29B 107.6 . . ? C29 C30 C31 113.2(6) . . ? C29 C30 H30A 108.9 . . ? C31 C30 H30A 108.9 . . ? C29 C30 H30B 108.9 . . ? C31 C30 H30B 108.9 . . ? H30A C30 H30B 107.8 . . ? C32 C31 C30 115.1(7) . . ? C32 C31 H31A 108.5 . . ? C30 C31 H31A 108.5 . . ? C32 C31 H31B 108.5 . . ? C30 C31 H31B 108.5 . . ? H31A C31 H31B 107.5 . . ? C33 C32 C31 114.9(8) . . ? C33 C32 H32A 108.6 . . ? C31 C32 H32A 108.6 . . ? C33 C32 H32B 108.6 . . ? C31 C32 H32B 108.6 . . ? H32A C32 H32B 107.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 S12 115.8(7) . . ? C35 C34 H34A 108.3 . . ? S12 C34 H34A 108.3 . . ? C35 C34 H34B 108.3 . . ? S12 C34 H34B 108.3 . . ? H34A C34 H34B 107.4 . . ? C36 C35 C34 113.7(7) . . ? C36 C35 H35A 108.8 . . ? C34 C35 H35A 108.8 . . ? C36 C35 H35B 108.8 . . ? C34 C35 H35B 108.8 . . ? H35A C35 H35B 107.7 . . ? C37 C36 C35 114.5(8) . . ? C37 C36 H36A 108.6 . . ? C35 C36 H36A 108.6 . . ? C37 C36 H36B 108.6 . . ? C35 C36 H36B 108.6 . . ? H36A C36 H36B 107.6 . . ? C36 C37 C38 112.1(8) . . ? C36 C37 H37A 109.2 . . ? C38 C37 H37A 109.2 . . ? C36 C37 H37B 109.2 . . ? C38 C37 H37B 109.2 . . ? H37A C37 H37B 107.9 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C35A C34A S12 107.5(9) . . ? C35A C34A H34C 110.2 . . ? S12 C34A H34C 110.2 . . ? C35A C34A H34D 110.2 . . ? S12 C34A H34D 110.2 . . ? H34C C34A H34D 108.5 . . ? C34A C35A C36A 109.0(8) . . ? C34A C35A H35C 109.9 . . ? C36A C35A H35C 109.9 . . ? C34A C35A H35D 109.9 . . ? C36A C35A H35D 109.9 . . ? H35C C35A H35D 108.3 . . ? C37A C36A C35A 111.4(9) . . ? C37A C36A H36C 109.3 . . ? C35A C36A H36C 109.3 . . ? C37A C36A H36D 109.3 . . ? C35A C36A H36D 109.3 . . ? H36C C36A H36D 108.0 . . ? C36A C37A C38A 110.6(9) . . ? C36A C37A H37C 109.5 . . ? C38A C37A H37C 109.5 . . ? C36A C37A H37D 109.5 . . ? C38A C37A H37D 109.5 . . ? H37C C37A H37D 108.1 . . ? C37A C38A H38D 109.5 . . ? C37A C38A H38E 109.5 . . ? H38D C38A H38E 109.5 . . ? C37A C38A H38F 109.5 . . ? H38D C38A H38F 109.5 . . ? H38E C38A H38F 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 C2 S1 S3 C7 -86.5(3) . . . . ? C4 N1 C1 C2 1.8(7) . . . . ? C5 N1 C1 C2 -177.8(6) . . . . ? C4 N1 C1 Br1 -178.4(4) . . . . ? C5 N1 C1 Br1 2.0(9) . . . . ? N1 C1 C2 C3 -0.6(7) . . . . ? Br1 C1 C2 C3 179.6(5) . . . . ? N1 C1 C2 S1 -169.3(5) . . . . ? Br1 C1 C2 S1 11.0(10) . . . . ? S3 S1 C2 C1 -96.4(6) . . . . ? S3 S1 C2 C3 96.7(5) . . . . ? C1 C2 C3 C4 -0.8(7) . . . . ? S1 C2 C3 C4 168.1(5) . . . . ? C1 C2 C3 S2 -177.1(5) . . . . ? S1 C2 C3 S2 -8.1(9) . . . . ? C15 S2 C3 C4 60.7(7) . . . . ? C15 S2 C3 C2 -123.8(6) . . . . ? C2 C3 C4 N1 2.0(7) . . . . ? S2 C3 C4 N1 178.1(5) . . . . ? C2 C3 C4 Br2 -177.5(5) . . . . ? S2 C3 C4 Br2 -1.3(10) . . . . ? C1 N1 C4 C3 -2.3(7) . . . . ? C5 N1 C4 C3 177.3(6) . . . . ? C1 N1 C4 Br2 177.1(4) . . . . ? C5 N1 C4 Br2 -3.3(9) . . . . ? C9 N2 C6 C7 0.5(8) . . . . ? C10 N2 C6 C7 178.5(6) . . . . ? C9 N2 C6 Br3 -176.8(5) . . . . ? C10 N2 C6 Br3 1.2(9) . . . . ? N2 C6 C7 C8 0.3(8) . . . . ? Br3 C6 C7 C8 177.3(5) . . . . ? N2 C6 C7 S3 -172.1(5) . . . . ? Br3 C6 C7 S3 4.8(10) . . . . ? S1 S3 C7 C6 -102.6(6) . . . . ? S1 S3 C7 C8 86.4(6) . . . . ? C6 C7 C8 C9 -1.0(7) . . . . ? S3 C7 C8 C9 171.6(5) . . . . ? C6 C7 C8 S4 -174.8(5) . . . . ? S3 C7 C8 S4 -2.2(9) . . . . ? C11 S4 C8 C9 57.3(7) . . . . ? C11 S4 C8 C7 -130.4(5) . . . . ? C7 C8 C9 N2 1.3(8) . . . . ? S4 C8 C9 N2 174.6(5) . . . . ? C7 C8 C9 Br4 -177.8(5) . . . . ? S4 C8 C9 Br4 -4.6(10) . . . . ? C6 N2 C9 C8 -1.1(8) . . . . ? C10 N2 C9 C8 -179.2(6) . . . . ? C6 N2 C9 Br4 178.1(5) . . . . ? C10 N2 C9 Br4 0.0(9) . . . . ? C8 S4 C11 C12 -139.9(5) . . . . ? C8 S4 C11 C15 46.1(6) . . . . ? C15 C11 C12 S6 22.1(10) . . . . ? S4 C11 C12 S6 -151.9(4) . . . . ? C15 C11 C12 S5 -159.0(5) . . . . ? S4 C11 C12 S5 27.0(7) . . . . ? C14 S6 C12 C11 173.2(6) . . . . ? C14 S6 C12 S5 -5.8(4) . . . . ? C13 S5 C12 C11 -175.8(6) . . . . ? C13 S5 C12 S6 3.2(4) . . . . ? C12 S5 C13 C14 1.8(6) . . . . ? C12 S5 C13 S7 -174.2(4) . . . . ? C19 S7 C13 C14 133.5(7) . . . . ? C19 S7 C13 S5 -50.8(5) . . . . ? S5 C13 C14 S8 175.4(4) . . . . ? S7 C13 C14 S8 -8.9(10) . . . . ? S5 C13 C14 S6 -6.2(8) . . . . ? S7 C13 C14 S6 169.5(4) . . . . ? C24 S8 C14 C13 -95.4(7) . . . . ? C24 S8 C14 S6 86.2(5) . . . . ? C12 S6 C14 C13 7.3(6) . . . . ? C12 S6 C14 S8 -174.2(4) . . . . ? C12 C11 C15 C16 44.1(10) . . . . ? S4 C11 C15 C16 -142.5(6) . . . . ? C12 C11 C15 S2 -144.5(6) . . . . ? S4 C11 C15 S2 28.9(8) . . . . ? C3 S2 C15 C16 -145.0(5) . . . . ? C3 S2 C15 C11 43.1(6) . . . . ? C11 C15 C16 S10 -174.8(5) . . . . ? S2 C15 C16 S10 13.1(8) . . . . ? C11 C15 C16 S9 4.6(10) . . . . ? S2 C15 C16 S9 -167.4(4) . . . . ? C18 S10 C16 C15 -171.4(6) . . . . ? C18 S10 C16 S9 9.1(4) . . . . ? C17 S9 C16 C15 171.2(6) . . . . ? C17 S9 C16 S10 -9.4(4) . . . . ? C16 S9 C17 C18 6.3(6) . . . . ? C16 S9 C17 S11 -177.9(4) . . . . ? C29 S11 C17 C18 -135.3(7) . . . . ? C29 S11 C17 S9 49.2(5) . . . . ? S9 C17 C18 S10 -0.8(8) . . . . ? S11 C17 C18 S10 -176.1(4) . . . . ? S9 C17 C18 S12 170.9(4) . . . . ? S11 C17 C18 S12 -4.4(10) . . . . ? C16 S10 C18 C17 -5.2(6) . . . . ? C16 S10 C18 S12 -177.5(4) . . . . ? C34A S12 C18 C17 73.7(8) . . . . ? C34 S12 C18 C17 108.7(7) . . . . ? C34A S12 C18 S10 -114.7(6) . . . . ? C34 S12 C18 S10 -79.7(5) . . . . ? C13 S7 C19 C20 -70.6(6) . . . . ? S7 C19 C20 C21 168.6(5) . . . . ? C19 C20 C21 C22 174.0(6) . . . . ? C20 C21 C22 C23 172.0(6) . . . . ? C14 S8 C24 C25 -71.2(6) . . . . ? S8 C24 C25 C26 -54.3(9) . . . . ? C24 C25 C26 C27 -59.6(10) . . . . ? C25 C26 C27 C28 -178.9(8) . . . . ? C17 S11 C29 C30 60.7(6) . . . . ? S11 C29 C30 C31 174.4(5) . . . . ? C29 C30 C31 C32 -177.6(7) . . . . ? C30 C31 C32 C33 64.9(12) . . . . ? C18 S12 C34 C35 -79.2(9) . . . . ? C34A S12 C34 C35 29.8(13) . . . . ? S12 C34 C35 C36 170.3(7) . . . . ? C34 C35 C36 C37 73.2(14) . . . . ? C35 C36 C37 C38 175.0(13) . . . . ? C18 S12 C34A C35A 76.7(14) . . . . ? C34 S12 C34A C35A -3.0(11) . . . . ? S12 C34A C35A C36A 176.9(15) . . . . ? C34A C35A C36A C37A -173.8(18) . . . . ? C35A C36A C37A C38A 176.9(19) . . . . ? #============================================================================= data_4b _database_code_depnum_ccdc_archive 'CCDC 649634' _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H50 I4 N2 S12' _chemical_formula_sum 'C38 H50 I4 N2 S12' _chemical_formula_weight 1427.12 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' I I -0.4742 1.8119 '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 11.6853(3) _cell_length_b 14.9902(4) _cell_length_c 16.1737(4) _cell_angle_alpha 112.847(1) _cell_angle_beta 90.668(1) _cell_angle_gamma 105.679(1) _cell_volume 2491.85(11) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4290 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 27.32 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.902 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 3.035 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.442 _exptl_absorpt_correction_T_max 0.888 _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.498369 ; _exptl_special_details ; Shamefully, the crystal fell off the fibre during data collection. As a result, the completeness is a little less than might be desirable. However, the quality of the refinement is very good, the data:parameter ratio remains around 24:1 and the analogous bromo-derivative has been shown to be isostructural. Under these circumstances, the experiment was NOT repeated. The pentyl chains are refined without restraint, giving some moderately large displacement parameters. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 20960 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0775 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 28.97 _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 28.97 _diffrn_measured_fraction_theta_full 0.922 _reflns_number_total 12179 _reflns_number_gt 8144 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-22 (Bruker-Nonius, 2004)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a (Bruker, 2003)' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL v.6.10 (Sheldrick, 2000)' _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^)+(0.0283P)^2^] 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 12179 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0803 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.838 _refine_diff_density_min -0.772 _refine_diff_density_rms 0.133 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 I1 I 0.04072(3) 0.60490(3) 0.678898(19) 0.03312(8) Uani 1 1 d . . . I2 I 0.33748(3) 0.40197(2) 0.404315(19) 0.02793(8) Uani 1 1 d . . . I3 I 0.35913(3) 1.10455(2) 0.60268(2) 0.03090(8) Uani 1 1 d . . . I4 I 0.32273(3) 0.80473(2) 0.215871(19) 0.03206(8) Uani 1 1 d . . . S1 S 0.28262(9) 0.79551(8) 0.63596(6) 0.0212(2) Uani 1 1 d . . . S2 S 0.42932(8) 0.67819(7) 0.46354(6) 0.0166(2) Uani 1 1 d . . . S3 S 0.17816(9) 0.84774(8) 0.57183(7) 0.0217(2) Uani 1 1 d . . . S4 S 0.16989(8) 0.67469(7) 0.35704(6) 0.0169(2) Uani 1 1 d . . . S5 S 0.09116(9) 0.52131(8) 0.15789(6) 0.0198(2) Uani 1 1 d . . . S6 S 0.24790(9) 0.40765(8) 0.18072(7) 0.0196(2) Uani 1 1 d . . . S7 S -0.03992(9) 0.35533(9) -0.01920(7) 0.0258(2) Uani 1 1 d . . . S8 S 0.12011(10) 0.21637(8) 0.02222(7) 0.0274(3) Uani 1 1 d . . . S9 S 0.46696(8) 0.57870(8) 0.17755(6) 0.0195(2) Uani 1 1 d . . . S10 S 0.62061(8) 0.61858(8) 0.33958(6) 0.0174(2) Uani 1 1 d . . . S11 S 0.66761(9) 0.59068(8) 0.06538(7) 0.0234(2) Uani 1 1 d . . . S12 S 0.84462(9) 0.62998(8) 0.25018(7) 0.0231(2) Uani 1 1 d . . . N1 N 0.1796(3) 0.4975(2) 0.5377(2) 0.0184(7) Uani 1 1 d . . . N2 N 0.3530(3) 0.9589(2) 0.4098(2) 0.0199(7) Uani 1 1 d . . . C1 C 0.1668(3) 0.5903(3) 0.5910(2) 0.0186(9) Uani 1 1 d . . . C2 C 0.2482(3) 0.6652(3) 0.5740(2) 0.0161(8) Uani 1 1 d . . . C3 C 0.3135(3) 0.6158(3) 0.5070(2) 0.0152(8) Uani 1 1 d . . . C4 C 0.2722(3) 0.5144(3) 0.4873(2) 0.0164(8) Uani 1 1 d . . . C5 C 0.1085(4) 0.3995(3) 0.5335(3) 0.0288(10) Uani 1 1 d . . . H5A H 0.0490 0.4091 0.5758 0.043 Uiso 1 1 calc R . . H5B H 0.1612 0.3664 0.5501 0.043 Uiso 1 1 calc R . . H5C H 0.0675 0.3568 0.4719 0.043 Uiso 1 1 calc R . . C6 C 0.3197(3) 0.9675(3) 0.4933(3) 0.0182(8) Uani 1 1 d . . . C7 C 0.2573(3) 0.8733(3) 0.4881(2) 0.0159(8) Uani 1 1 d . . . C8 C 0.2513(3) 0.8031(3) 0.3974(2) 0.0152(8) Uani 1 1 d . . . C9 C 0.3078(3) 0.8576(3) 0.3515(3) 0.0182(8) Uani 1 1 d . . . C10 C 0.4214(4) 1.0408(3) 0.3859(3) 0.0267(10) Uani 1 1 d . . . H10A H 0.4424 1.1051 0.4395 0.040 Uiso 1 1 calc R . . H10B H 0.3728 1.0454 0.3388 0.040 Uiso 1 1 calc R . . H10C H 0.4949 1.0266 0.3633 0.040 Uiso 1 1 calc R . . C11 C 0.2652(3) 0.6014(3) 0.3038(2) 0.0129(8) Uani 1 1 d . . . C12 C 0.2105(3) 0.5209(3) 0.2249(2) 0.0131(8) Uani 1 1 d . . . C13 C 0.0635(3) 0.3968(3) 0.0774(2) 0.0177(8) Uani 1 1 d . . . C14 C 0.1313(3) 0.3432(3) 0.0895(2) 0.0168(8) Uani 1 1 d . . . C15 C 0.3861(3) 0.6207(3) 0.3442(2) 0.0126(8) Uani 1 1 d . . . C16 C 0.4779(3) 0.6085(3) 0.2944(2) 0.0148(8) Uani 1 1 d . . . C17 C 0.6211(3) 0.6028(3) 0.1707(2) 0.0161(8) Uani 1 1 d . . . C18 C 0.6918(3) 0.6204(3) 0.2449(3) 0.0163(8) Uani 1 1 d . . . C19 C -0.1687(4) 0.3853(3) 0.0333(3) 0.0271(10) Uani 1 1 d . . . H19A H -0.1424 0.4549 0.0815 0.033 Uiso 1 1 calc R . . H19B H -0.2268 0.3839 -0.0125 0.033 Uiso 1 1 calc R . . C20 C -0.2305(4) 0.3124(3) 0.0738(3) 0.0298(10) Uani 1 1 d . . . H20A H -0.1687 0.3022 0.1087 0.036 Uiso 1 1 calc R . . H20B H -0.2715 0.2461 0.0240 0.036 Uiso 1 1 calc R . . C21 C -0.3216(4) 0.3462(3) 0.1355(3) 0.0308(11) Uani 1 1 d . . . H21A H -0.2807 0.4119 0.1862 0.037 Uiso 1 1 calc R . . H21B H -0.3833 0.3571 0.1011 0.037 Uiso 1 1 calc R . . C22 C -0.3827(4) 0.2714(4) 0.1738(3) 0.0365(12) Uani 1 1 d . . . H22A H -0.3209 0.2537 0.2015 0.044 Uiso 1 1 calc R . . H22B H -0.4324 0.2085 0.1238 0.044 Uiso 1 1 calc R . . C23 C -0.4614(4) 0.3115(4) 0.2441(3) 0.0487(14) Uani 1 1 d . . . H23A H -0.4980 0.2603 0.2671 0.073 Uiso 1 1 calc R . . H23B H -0.5245 0.3270 0.2165 0.073 Uiso 1 1 calc R . . H23C H -0.4127 0.3734 0.2941 0.073 Uiso 1 1 calc R . . C24 C 0.0370(4) 0.1547(4) 0.0898(3) 0.0368(12) Uani 1 1 d . . . H24A H -0.0343 0.1789 0.1037 0.044 Uiso 1 1 calc R . . H24B H 0.0074 0.0811 0.0515 0.044 Uiso 1 1 calc R . . C25 C 0.0994(4) 0.1681(4) 0.1770(3) 0.0431(13) Uani 1 1 d . . . H25A H 0.0445 0.1252 0.2022 0.052 Uiso 1 1 calc R . . H25B H 0.1152 0.2396 0.2204 0.052 Uiso 1 1 calc R . . C26 C 0.2167(4) 0.1424(4) 0.1707(3) 0.0403(12) Uani 1 1 d . . . H26A H 0.2515 0.1569 0.2323 0.048 Uiso 1 1 calc R . . H26B H 0.2732 0.1877 0.1484 0.048 Uiso 1 1 calc R . . C27 C 0.2070(5) 0.0328(4) 0.1094(4) 0.0484(14) Uani 1 1 d . . . H27A H 0.1499 -0.0131 0.1307 0.058 Uiso 1 1 calc R . . H27B H 0.1745 0.0182 0.0471 0.058 Uiso 1 1 calc R . . C28 C 0.3269(5) 0.0113(5) 0.1074(4) 0.0615(17) Uani 1 1 d . . . H28A H 0.3158 -0.0601 0.0682 0.092 Uiso 1 1 calc R . . H28B H 0.3594 0.0254 0.1688 0.092 Uiso 1 1 calc R . . H28C H 0.3828 0.0546 0.0840 0.092 Uiso 1 1 calc R . . C29 C 0.5950(4) 0.6721(3) 0.0394(3) 0.0234(9) Uani 1 1 d . . . H29A H 0.6115 0.6698 -0.0211 0.028 Uiso 1 1 calc R . . H29B H 0.5072 0.6449 0.0369 0.028 Uiso 1 1 calc R . . C30 C 0.6362(4) 0.7815(3) 0.1077(3) 0.0265(10) Uani 1 1 d . . . H30A H 0.6064 0.7858 0.1658 0.032 Uiso 1 1 calc R . . H30B H 0.7249 0.8054 0.1186 0.032 Uiso 1 1 calc R . . C31 C 0.5915(4) 0.8499(3) 0.0756(3) 0.0338(11) Uani 1 1 d . . . H31A H 0.5027 0.8264 0.0658 0.041 Uiso 1 1 calc R . . H31B H 0.6195 0.8438 0.0166 0.041 Uiso 1 1 calc R . . C32 C 0.6334(4) 0.9608(4) 0.1414(3) 0.0430(13) Uani 1 1 d . . . H32A H 0.5951 0.9997 0.1187 0.052 Uiso 1 1 calc R . . H32B H 0.6063 0.9667 0.2006 0.052 Uiso 1 1 calc R . . C33 C 0.7660(5) 1.0069(4) 0.1552(4) 0.0551(16) Uani 1 1 d . . . H33A H 0.7871 1.0777 0.1991 0.083 Uiso 1 1 calc R . . H33B H 0.7934 1.0042 0.0974 0.083 Uiso 1 1 calc R . . H33C H 0.8048 0.9691 0.1780 0.083 Uiso 1 1 calc R . . C34 C 0.9112(4) 0.7597(3) 0.3326(3) 0.0348(12) Uani 1 1 d . . . H34A H 0.8512 0.7800 0.3729 0.042 Uiso 1 1 calc R . . H34B H 0.9799 0.7618 0.3704 0.042 Uiso 1 1 calc R . . C35 C 0.9530(4) 0.8341(4) 0.2929(3) 0.0433(13) Uani 1 1 d . . . H35A H 0.8836 0.8369 0.2594 0.052 Uiso 1 1 calc R . . H35B H 1.0088 0.8119 0.2492 0.052 Uiso 1 1 calc R . . C36 C 1.0166(4) 0.9401(4) 0.3650(3) 0.0423(13) Uani 1 1 d . . . H36A H 0.9574 0.9640 0.4044 0.051 Uiso 1 1 calc R . . H36B H 1.0788 0.9344 0.4032 0.051 Uiso 1 1 calc R . . C37 C 1.0734(6) 1.0172(4) 0.3323(4) 0.0621(17) Uani 1 1 d . . . H37A H 1.0121 1.0213 0.2923 0.075 Uiso 1 1 calc R . . H37B H 1.1352 0.9949 0.2951 0.075 Uiso 1 1 calc R . . C38 C 1.1305(4) 1.1204(4) 0.4035(3) 0.0457(13) Uani 1 1 d . . . H38A H 1.1669 1.1664 0.3750 0.069 Uiso 1 1 calc R . . H38B H 1.1926 1.1179 0.4431 0.069 Uiso 1 1 calc R . . H38C H 1.0697 1.1450 0.4393 0.069 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 I1 0.02979(16) 0.0445(2) 0.02894(16) 0.02029(15) 0.01462(13) 0.00851(14) I2 0.03742(17) 0.02028(16) 0.02759(15) 0.00921(12) 0.00674(12) 0.01160(13) I3 0.03323(17) 0.01704(15) 0.03274(16) 0.00168(13) 0.00023(13) 0.00530(12) I4 0.04257(18) 0.02839(17) 0.02254(15) 0.01134(13) 0.00912(13) 0.00473(14) S1 0.0304(6) 0.0166(5) 0.0152(5) 0.0062(4) 0.0047(4) 0.0053(4) S2 0.0152(5) 0.0167(5) 0.0132(5) 0.0057(4) 0.0019(4) -0.0020(4) S3 0.0246(5) 0.0198(6) 0.0244(5) 0.0107(4) 0.0108(4) 0.0094(4) S4 0.0131(5) 0.0114(5) 0.0223(5) 0.0042(4) 0.0055(4) 0.0014(4) S5 0.0215(5) 0.0167(5) 0.0191(5) 0.0052(4) -0.0021(4) 0.0059(4) S6 0.0190(5) 0.0137(5) 0.0218(5) 0.0034(4) -0.0019(4) 0.0041(4) S7 0.0263(6) 0.0298(6) 0.0163(5) 0.0053(5) -0.0034(4) 0.0068(5) S8 0.0303(6) 0.0161(6) 0.0255(6) -0.0011(5) -0.0005(5) 0.0052(5) S9 0.0145(5) 0.0285(6) 0.0143(5) 0.0093(4) 0.0028(4) 0.0034(4) S10 0.0139(5) 0.0236(6) 0.0173(5) 0.0110(4) 0.0035(4) 0.0055(4) S11 0.0283(6) 0.0257(6) 0.0180(5) 0.0094(4) 0.0117(4) 0.0094(5) S12 0.0151(5) 0.0235(6) 0.0297(6) 0.0091(5) 0.0066(4) 0.0066(4) N1 0.0202(17) 0.0138(18) 0.0210(17) 0.0118(14) 0.0025(14) -0.0022(14) N2 0.0168(17) 0.0152(18) 0.0267(18) 0.0082(15) 0.0053(14) 0.0034(14) C1 0.019(2) 0.026(2) 0.0162(19) 0.0151(18) 0.0031(16) 0.0057(18) C2 0.019(2) 0.018(2) 0.0144(18) 0.0085(16) 0.0035(15) 0.0067(17) C3 0.0142(19) 0.018(2) 0.0155(19) 0.0106(17) 0.0020(15) 0.0031(16) C4 0.0166(19) 0.016(2) 0.0136(19) 0.0050(16) 0.0015(15) 0.0026(16) C5 0.028(2) 0.025(3) 0.034(3) 0.019(2) 0.004(2) -0.002(2) C6 0.021(2) 0.013(2) 0.020(2) 0.0048(17) 0.0029(16) 0.0062(17) C7 0.0142(19) 0.013(2) 0.022(2) 0.0069(17) 0.0029(16) 0.0060(16) C8 0.0102(18) 0.013(2) 0.0188(19) 0.0033(16) -0.0004(15) 0.0031(15) C9 0.0154(19) 0.014(2) 0.023(2) 0.0056(17) 0.0013(16) 0.0024(16) C10 0.029(2) 0.016(2) 0.033(2) 0.013(2) 0.0104(19) 0.0014(19) C11 0.0137(18) 0.0097(19) 0.0145(18) 0.0053(15) 0.0028(15) 0.0017(15) C12 0.0095(17) 0.014(2) 0.0175(19) 0.0098(16) 0.0052(15) 0.0010(15) C13 0.0148(19) 0.018(2) 0.0144(19) 0.0058(17) 0.0005(15) -0.0022(16) C14 0.019(2) 0.013(2) 0.0145(19) 0.0047(16) 0.0007(15) 0.0015(16) C15 0.0151(18) 0.0106(19) 0.0107(17) 0.0053(15) 0.0015(14) 0.0000(15) C16 0.0160(19) 0.015(2) 0.0134(18) 0.0081(16) 0.0010(15) 0.0003(16) C17 0.0175(19) 0.011(2) 0.019(2) 0.0058(16) 0.0060(16) 0.0025(16) C18 0.0123(18) 0.013(2) 0.023(2) 0.0070(17) 0.0068(16) 0.0027(16) C19 0.025(2) 0.025(2) 0.026(2) 0.0075(19) -0.0060(18) 0.0036(19) C20 0.031(2) 0.021(2) 0.034(3) 0.009(2) -0.003(2) 0.005(2) C21 0.027(2) 0.023(2) 0.038(3) 0.007(2) -0.003(2) 0.009(2) C22 0.031(3) 0.041(3) 0.038(3) 0.017(2) 0.003(2) 0.008(2) C23 0.034(3) 0.059(4) 0.055(3) 0.027(3) 0.012(3) 0.011(3) C24 0.030(3) 0.020(3) 0.056(3) 0.014(2) 0.006(2) 0.002(2) C25 0.046(3) 0.032(3) 0.053(3) 0.021(3) 0.013(3) 0.008(2) C26 0.051(3) 0.029(3) 0.038(3) 0.017(2) -0.005(2) 0.002(2) C27 0.058(4) 0.031(3) 0.051(3) 0.015(3) 0.001(3) 0.006(3) C28 0.068(4) 0.050(4) 0.079(4) 0.034(3) 0.000(3) 0.024(3) C29 0.027(2) 0.026(2) 0.018(2) 0.0145(18) 0.0043(17) -0.0005(19) C30 0.031(2) 0.024(2) 0.021(2) 0.0083(19) 0.0039(18) 0.006(2) C31 0.042(3) 0.029(3) 0.033(3) 0.016(2) 0.013(2) 0.010(2) C32 0.056(3) 0.035(3) 0.044(3) 0.019(3) 0.023(3) 0.017(3) C33 0.061(4) 0.030(3) 0.053(3) 0.003(3) 0.026(3) 0.002(3) C34 0.025(2) 0.027(3) 0.042(3) 0.004(2) -0.004(2) 0.006(2) C35 0.038(3) 0.028(3) 0.058(3) 0.015(3) 0.018(3) 0.003(2) C36 0.037(3) 0.036(3) 0.056(3) 0.024(3) 0.011(2) 0.005(2) C37 0.075(4) 0.037(4) 0.061(4) 0.021(3) 0.009(3) -0.006(3) C38 0.041(3) 0.035(3) 0.054(3) 0.016(3) 0.007(3) 0.004(2) _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 I1 C1 2.054(4) . ? I2 C4 2.046(4) . ? I3 C6 2.052(4) . ? I4 C9 2.051(4) . ? S1 C2 1.740(4) . ? S1 S3 2.0728(14) . ? S2 C3 1.745(4) . ? S2 C15 1.782(3) . ? S3 C7 1.754(4) . ? S4 C8 1.748(4) . ? S4 C11 1.772(4) . ? S5 C13 1.749(4) . ? S5 C12 1.759(3) . ? S6 C12 1.747(4) . ? S6 C14 1.761(4) . ? S7 C13 1.756(4) . ? S7 C19 1.813(4) . ? S8 C14 1.752(4) . ? S8 C24 1.821(5) . ? S9 C17 1.752(4) . ? S9 C16 1.760(4) . ? S10 C18 1.757(4) . ? S10 C16 1.757(4) . ? S11 C17 1.751(4) . ? S11 C29 1.825(4) . ? S12 C18 1.751(4) . ? S12 C34 1.819(4) . ? N1 C1 1.373(5) . ? N1 C4 1.389(5) . ? N1 C5 1.455(5) . ? N2 C6 1.378(5) . ? N2 C9 1.384(5) . ? N2 C10 1.463(5) . ? C1 C2 1.381(5) . ? C2 C3 1.417(5) . ? C3 C4 1.368(5) . ? C5 H5A 0.980 . ? C5 H5B 0.980 . ? C5 H5C 0.980 . ? C6 C7 1.372(5) . ? C7 C8 1.423(5) . ? C8 C9 1.358(5) . ? C10 H10A 0.980 . ? C10 H10B 0.980 . ? C10 H10C 0.980 . ? C11 C12 1.364(5) . ? C11 C15 1.455(5) . ? C13 C14 1.333(5) . ? C15 C16 1.358(5) . ? C17 C18 1.344(5) . ? C19 C20 1.512(6) . ? C19 H19A 0.990 . ? C19 H19B 0.990 . ? C20 C21 1.520(6) . ? C20 H20A 0.990 . ? C20 H20B 0.990 . ? C21 C22 1.505(6) . ? C21 H21A 0.990 . ? C21 H21B 0.990 . ? C22 C23 1.515(6) . ? C22 H22A 0.990 . ? C22 H22B 0.990 . ? C23 H23A 0.980 . ? C23 H23B 0.980 . ? C23 H23C 0.980 . ? C24 C25 1.496(6) . ? C24 H24A 0.990 . ? C24 H24B 0.990 . ? C25 C26 1.515(6) . ? C25 H25A 0.990 . ? C25 H25B 0.990 . ? C26 C27 1.525(7) . ? C26 H26A 0.990 . ? C26 H26B 0.990 . ? C27 C28 1.519(7) . ? C27 H27A 0.990 . ? C27 H27B 0.990 . ? C28 H28A 0.980 . ? C28 H28B 0.980 . ? C28 H28C 0.980 . ? C29 C30 1.515(6) . ? C29 H29A 0.990 . ? C29 H29B 0.990 . ? C30 C31 1.513(6) . ? C30 H30A 0.990 . ? C30 H30B 0.990 . ? C31 C32 1.520(6) . ? C31 H31A 0.990 . ? C31 H31B 0.990 . ? C32 C33 1.491(7) . ? C32 H32A 0.990 . ? C32 H32B 0.990 . ? C33 H33A 0.980 . ? C33 H33B 0.980 . ? C33 H33C 0.980 . ? C34 C35 1.472(7) . ? C34 H34A 0.990 . ? C34 H34B 0.990 . ? C35 C36 1.529(6) . ? C35 H35A 0.990 . ? C35 H35B 0.990 . ? C36 C37 1.458(7) . ? C36 H36A 0.990 . ? C36 H36B 0.990 . ? C37 C38 1.485(7) . ? C37 H37A 0.990 . ? C37 H37B 0.990 . ? C38 H38A 0.980 . ? C38 H38B 0.980 . ? C38 H38C 0.980 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 S3 107.08(13) . . ? C3 S2 C15 104.95(17) . . ? C7 S3 S1 107.03(13) . . ? C8 S4 C11 108.65(17) . . ? C13 S5 C12 96.36(17) . . ? C12 S6 C14 96.44(17) . . ? C13 S7 C19 100.26(18) . . ? C14 S8 C24 100.2(2) . . ? C17 S9 C16 96.19(17) . . ? C18 S10 C16 96.17(17) . . ? C17 S11 C29 100.35(18) . . ? C18 S12 C34 101.68(19) . . ? C1 N1 C4 107.3(3) . . ? C1 N1 C5 126.5(3) . . ? C4 N1 C5 126.2(3) . . ? C6 N2 C9 107.0(3) . . ? C6 N2 C10 127.0(3) . . ? C9 N2 C10 126.0(3) . . ? N1 C1 C2 109.5(3) . . ? N1 C1 I1 121.9(3) . . ? C2 C1 I1 128.7(3) . . ? C1 C2 C3 106.7(3) . . ? C1 C2 S1 126.7(3) . . ? C3 C2 S1 125.8(3) . . ? C4 C3 C2 107.5(3) . . ? C4 C3 S2 128.1(3) . . ? C2 C3 S2 124.4(3) . . ? C3 C4 N1 109.1(3) . . ? C3 C4 I2 127.6(3) . . ? N1 C4 I2 123.2(3) . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 N2 109.2(3) . . ? C7 C6 I3 128.5(3) . . ? N2 C6 I3 122.3(3) . . ? C6 C7 C8 107.1(3) . . ? C6 C7 S3 126.0(3) . . ? C8 C7 S3 126.1(3) . . ? C9 C8 C7 106.8(3) . . ? C9 C8 S4 129.7(3) . . ? C7 C8 S4 123.2(3) . . ? C8 C9 N2 109.8(3) . . ? C8 C9 I4 127.2(3) . . ? N2 C9 I4 123.0(3) . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C15 123.7(3) . . ? C12 C11 S4 113.1(3) . . ? C15 C11 S4 123.1(3) . . ? C11 C12 S6 124.7(3) . . ? C11 C12 S5 122.3(3) . . ? S6 C12 S5 113.1(2) . . ? C14 C13 S5 117.2(3) . . ? C14 C13 S7 124.2(3) . . ? S5 C13 S7 118.2(2) . . ? C13 C14 S8 127.0(3) . . ? C13 C14 S6 116.6(3) . . ? S8 C14 S6 116.4(2) . . ? C16 C15 C11 122.6(3) . . ? C16 C15 S2 114.6(3) . . ? C11 C15 S2 122.3(3) . . ? C15 C16 S10 123.5(3) . . ? C15 C16 S9 124.0(3) . . ? S10 C16 S9 112.4(2) . . ? C18 C17 S11 125.7(3) . . ? C18 C17 S9 116.8(3) . . ? S11 C17 S9 117.3(2) . . ? C17 C18 S12 125.1(3) . . ? C17 C18 S10 116.7(3) . . ? S12 C18 S10 117.7(2) . . ? C20 C19 S7 112.7(3) . . ? C20 C19 H19A 109.0 . . ? S7 C19 H19A 109.0 . . ? C20 C19 H19B 109.0 . . ? S7 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C19 C20 C21 114.8(4) . . ? C19 C20 H20A 108.6 . . ? C21 C20 H20A 108.6 . . ? C19 C20 H20B 108.6 . . ? C21 C20 H20B 108.6 . . ? H20A C20 H20B 107.5 . . ? C22 C21 C20 113.5(4) . . ? C22 C21 H21A 108.9 . . ? C20 C21 H21A 108.9 . . ? C22 C21 H21B 108.9 . . ? C20 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C21 C22 C23 112.9(4) . . ? C21 C22 H22A 109.0 . . ? C23 C22 H22A 109.0 . . ? C21 C22 H22B 109.0 . . ? C23 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 S8 118.8(3) . . ? C25 C24 H24A 107.6 . . ? S8 C24 H24A 107.6 . . ? C25 C24 H24B 107.6 . . ? S8 C24 H24B 107.6 . . ? H24A C24 H24B 107.1 . . ? C24 C25 C26 115.5(4) . . ? C24 C25 H25A 108.4 . . ? C26 C25 H25A 108.4 . . ? C24 C25 H25B 108.4 . . ? C26 C25 H25B 108.4 . . ? H25A C25 H25B 107.5 . . ? C25 C26 C27 115.0(4) . . ? C25 C26 H26A 108.5 . . ? C27 C26 H26A 108.5 . . ? C25 C26 H26B 108.5 . . ? C27 C26 H26B 108.5 . . ? H26A C26 H26B 107.5 . . ? C28 C27 C26 112.5(4) . . ? C28 C27 H27A 109.1 . . ? C26 C27 H27A 109.1 . . ? C28 C27 H27B 109.1 . . ? C26 C27 H27B 109.1 . . ? H27A C27 H27B 107.8 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 S11 113.6(3) . . ? C30 C29 H29A 108.9 . . ? S11 C29 H29A 108.9 . . ? C30 C29 H29B 108.9 . . ? S11 C29 H29B 108.9 . . ? H29A C29 H29B 107.7 . . ? C31 C30 C29 111.9(3) . . ? C31 C30 H30A 109.2 . . ? C29 C30 H30A 109.2 . . ? C31 C30 H30B 109.2 . . ? C29 C30 H30B 109.2 . . ? H30A C30 H30B 107.9 . . ? C30 C31 C32 113.4(4) . . ? C30 C31 H31A 108.9 . . ? C32 C31 H31A 108.9 . . ? C30 C31 H31B 108.9 . . ? C32 C31 H31B 108.9 . . ? H31A C31 H31B 107.7 . . ? C33 C32 C31 113.6(4) . . ? C33 C32 H32A 108.8 . . ? C31 C32 H32A 108.8 . . ? C33 C32 H32B 108.8 . . ? C31 C32 H32B 108.8 . . ? H32A C32 H32B 107.7 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 S12 114.4(3) . . ? C35 C34 H34A 108.7 . . ? S12 C34 H34A 108.7 . . ? C35 C34 H34B 108.7 . . ? S12 C34 H34B 108.7 . . ? H34A C34 H34B 107.6 . . ? C34 C35 C36 112.0(4) . . ? C34 C35 H35A 109.2 . . ? C36 C35 H35A 109.2 . . ? C34 C35 H35B 109.2 . . ? C36 C35 H35B 109.2 . . ? H35A C35 H35B 107.9 . . ? C37 C36 C35 116.4(5) . . ? C37 C36 H36A 108.2 . . ? C35 C36 H36A 108.2 . . ? C37 C36 H36B 108.2 . . ? C35 C36 H36B 108.2 . . ? H36A C36 H36B 107.3 . . ? C36 C37 C38 115.5(5) . . ? C36 C37 H37A 108.4 . . ? C38 C37 H37A 108.4 . . ? C36 C37 H37B 108.4 . . ? C38 C37 H37B 108.4 . . ? H37A C37 H37B 107.5 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 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 C2 S1 S3 C7 -86.8(2) . . . . ? C4 N1 C1 C2 1.1(4) . . . . ? C5 N1 C1 C2 -178.2(3) . . . . ? C4 N1 C1 I1 -179.6(2) . . . . ? C5 N1 C1 I1 1.1(5) . . . . ? N1 C1 C2 C3 0.1(4) . . . . ? I1 C1 C2 C3 -179.1(3) . . . . ? N1 C1 C2 S1 -169.6(3) . . . . ? I1 C1 C2 S1 11.2(5) . . . . ? S3 S1 C2 C1 -95.6(3) . . . . ? S3 S1 C2 C3 96.6(3) . . . . ? C1 C2 C3 C4 -1.3(4) . . . . ? S1 C2 C3 C4 168.5(3) . . . . ? C1 C2 C3 S2 -178.9(3) . . . . ? S1 C2 C3 S2 -9.1(5) . . . . ? C15 S2 C3 C4 58.2(4) . . . . ? C15 S2 C3 C2 -124.7(3) . . . . ? C2 C3 C4 N1 2.0(4) . . . . ? S2 C3 C4 N1 179.5(3) . . . . ? C2 C3 C4 I2 -174.4(3) . . . . ? S2 C3 C4 I2 3.0(5) . . . . ? C1 N1 C4 C3 -2.0(4) . . . . ? C5 N1 C4 C3 177.3(3) . . . . ? C1 N1 C4 I2 174.7(2) . . . . ? C5 N1 C4 I2 -6.0(5) . . . . ? C9 N2 C6 C7 1.3(4) . . . . ? C10 N2 C6 C7 -179.6(3) . . . . ? C9 N2 C6 I3 -177.3(2) . . . . ? C10 N2 C6 I3 1.8(5) . . . . ? N2 C6 C7 C8 0.0(4) . . . . ? I3 C6 C7 C8 178.5(3) . . . . ? N2 C6 C7 S3 -170.2(3) . . . . ? I3 C6 C7 S3 8.4(5) . . . . ? S1 S3 C7 C6 -103.2(3) . . . . ? S1 S3 C7 C8 88.5(3) . . . . ? C6 C7 C8 C9 -1.2(4) . . . . ? S3 C7 C8 C9 168.9(3) . . . . ? C6 C7 C8 S4 -174.9(3) . . . . ? S3 C7 C8 S4 -4.8(5) . . . . ? C11 S4 C8 C9 59.6(4) . . . . ? C11 S4 C8 C7 -128.3(3) . . . . ? C7 C8 C9 N2 2.1(4) . . . . ? S4 C8 C9 N2 175.2(3) . . . . ? C7 C8 C9 I4 -175.9(3) . . . . ? S4 C8 C9 I4 -2.8(5) . . . . ? C6 N2 C9 C8 -2.1(4) . . . . ? C10 N2 C9 C8 178.8(3) . . . . ? C6 N2 C9 I4 176.0(2) . . . . ? C10 N2 C9 I4 -3.1(5) . . . . ? C8 S4 C11 C12 -137.9(3) . . . . ? C8 S4 C11 C15 46.8(4) . . . . ? C15 C11 C12 S6 23.7(6) . . . . ? S4 C11 C12 S6 -151.6(2) . . . . ? C15 C11 C12 S5 -157.4(3) . . . . ? S4 C11 C12 S5 27.3(4) . . . . ? C14 S6 C12 C11 174.4(3) . . . . ? C14 S6 C12 S5 -4.6(2) . . . . ? C13 S5 C12 C11 -176.3(3) . . . . ? C13 S5 C12 S6 2.7(2) . . . . ? C12 S5 C13 C14 1.1(4) . . . . ? C12 S5 C13 S7 -172.5(2) . . . . ? C19 S7 C13 C14 133.0(4) . . . . ? C19 S7 C13 S5 -53.9(3) . . . . ? S5 C13 C14 S8 177.7(2) . . . . ? S7 C13 C14 S8 -9.1(6) . . . . ? S5 C13 C14 S6 -4.6(5) . . . . ? S7 C13 C14 S6 168.6(2) . . . . ? C24 S8 C14 C13 -99.7(4) . . . . ? C24 S8 C14 S6 82.6(3) . . . . ? C12 S6 C14 C13 5.6(4) . . . . ? C12 S6 C14 S8 -176.5(2) . . . . ? C12 C11 C15 C16 41.3(6) . . . . ? S4 C11 C15 C16 -143.9(3) . . . . ? C12 C11 C15 S2 -147.3(3) . . . . ? S4 C11 C15 S2 27.5(5) . . . . ? C3 S2 C15 C16 -142.5(3) . . . . ? C3 S2 C15 C11 45.5(3) . . . . ? C11 C15 C16 S10 -173.2(3) . . . . ? S2 C15 C16 S10 14.8(4) . . . . ? C11 C15 C16 S9 5.6(5) . . . . ? S2 C15 C16 S9 -166.4(2) . . . . ? C18 S10 C16 C15 -168.6(3) . . . . ? C18 S10 C16 S9 12.5(2) . . . . ? C17 S9 C16 C15 168.2(3) . . . . ? C17 S9 C16 S10 -12.9(2) . . . . ? C29 S11 C17 C18 -133.4(3) . . . . ? C29 S11 C17 S9 52.7(3) . . . . ? C16 S9 C17 C18 8.4(3) . . . . ? C16 S9 C17 S11 -177.1(2) . . . . ? S11 C17 C18 S12 -2.7(5) . . . . ? S9 C17 C18 S12 171.3(2) . . . . ? S11 C17 C18 S10 -174.7(2) . . . . ? S9 C17 C18 S10 -0.8(4) . . . . ? C34 S12 C18 C17 117.9(4) . . . . ? C34 S12 C18 S10 -70.1(3) . . . . ? C16 S10 C18 C17 -7.3(3) . . . . ? C16 S10 C18 S12 -180.0(2) . . . . ? C13 S7 C19 C20 -74.6(3) . . . . ? S7 C19 C20 C21 167.6(3) . . . . ? C19 C20 C21 C22 179.2(4) . . . . ? C20 C21 C22 C23 172.8(4) . . . . ? C14 S8 C24 C25 -71.5(4) . . . . ? S8 C24 C25 C26 -53.2(5) . . . . ? C24 C25 C26 C27 -60.8(6) . . . . ? C25 C26 C27 C28 -178.8(4) . . . . ? C17 S11 C29 C30 61.0(3) . . . . ? S11 C29 C30 C31 169.8(3) . . . . ? C29 C30 C31 C32 -178.7(4) . . . . ? C30 C31 C32 C33 63.5(6) . . . . ? C18 S12 C34 C35 -95.4(4) . . . . ? S12 C34 C35 C36 -175.6(3) . . . . ? C34 C35 C36 C37 173.4(5) . . . . ? C35 C36 C37 C38 177.7(4) . . . . ? #===END