Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Andrew Burrows' 'Jennifer E.V.Babb' 'Nichola J.Burke' 'M. Mahon' ; David M. K.Slade ; _publ_contact_author_name 'Dr Andrew Burrows' _publ_contact_author_address ; Department of Chemistry University of Bath Claverton Down Bath BA2 7AY UNITED KINGDOM ; _publ_contact_author_email A.D.BURROWS@BATH.AC.UK _publ_section_title ; Hydrogen-Bonded Linear Thiourea Hexads in Tetra-n-butylammonium Terephthalate Inclusion Compounds ; data_compound1_h01jeb2 _database_code_CSD 208153 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H104 N14 O6 S6' _chemical_formula_weight 1141.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4989(3) _cell_length_b 10.4456(4) _cell_length_c 19.6071(7) _cell_angle_alpha 102.0940(10) _cell_angle_beta 95.5280(10) _cell_angle_gamma 99.560(2) _cell_volume 1662.78(10) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.140 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 622 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method KappaCCD _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 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0748 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 25.38 _reflns_number_total 5892 _reflns_number_gt 3499 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'Denzo and Scalepack (otwinowski & Minor, 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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 [1.00000+0.00000exp(0.00(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+0.0000+0.0668*P+(0.0647P)^2^+0.0000sin\q/\l] where P = 0.00000Fo^2^ + 1.00000Fc^2^ ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5892 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1030 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1468 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.31148(9) 0.62510(8) 0.02286(4) 0.0624(2) Uani 1 1 d . . . S2 S 0.21123(9) 0.40655(9) 0.18412(4) 0.0706(3) Uani 1 1 d . . . S3 S 0.21133(9) 0.01696(8) 0.06352(3) 0.0611(2) Uani 1 1 d . . . O1 O 0.3814(3) -0.1011(2) 0.30877(11) 0.0942(8) Uani 1 1 d . . . O2 O 0.3802(3) 0.1144(2) 0.34244(10) 0.0752(6) Uani 1 1 d . . . O3 O 0.1243(4) 0.6799(3) 0.26515(19) 0.1372(13) Uani 1 1 d . . . N1 N 0.8750(3) 0.1682(3) 0.30345(12) 0.0638(7) Uani 1 1 d . . . N2 N 0.5467(3) 0.6438(3) -0.05485(14) 0.0769(8) Uani 1 1 d . . . H2A H 0.6068 0.6832 -0.0801 0.092 Uiso 1 1 calc R . . H2B H 0.5596 0.5670 -0.0486 0.092 Uiso 1 1 calc R . . N3 N 0.4216(3) 0.8195(3) -0.03746(13) 0.0667(7) Uani 1 1 d . . . H3A H 0.4841 0.8555 -0.0631 0.080 Uiso 1 1 calc R . . H3B H 0.3502 0.8604 -0.0194 0.080 Uiso 1 1 calc R . . N4 N 0.0135(3) 0.2856(3) 0.06797(14) 0.0752(8) Uani 1 1 d . . . H4A H -0.0633 0.2816 0.0352 0.090 Uiso 1 1 calc R . . H4B H 0.0601 0.2185 0.0678 0.090 Uiso 1 1 calc R . . N5 N -0.0153(3) 0.4966(3) 0.11696(15) 0.0799(8) Uani 1 1 d . . . H5A H -0.0917 0.4898 0.0835 0.096 Uiso 1 1 calc R . . H5B H 0.0124 0.5690 0.1493 0.096 Uiso 1 1 calc R . . N6 N 0.3003(3) -0.1080(3) 0.16081(12) 0.0672(7) Uani 1 1 d . . . H6A H 0.3316 -0.1119 0.2033 0.081 Uiso 1 1 calc R . . H6B H 0.2873 -0.1780 0.1272 0.081 Uiso 1 1 calc R . . N7 N 0.2939(3) 0.1093(3) 0.20046(12) 0.0659(7) Uani 1 1 d . . . H7A H 0.3253 0.1027 0.2424 0.079 Uiso 1 1 calc R . . H7B H 0.2765 0.1843 0.1931 0.079 Uiso 1 1 calc R . . C1 C 0.7494(3) 0.2566(4) 0.30521(18) 0.0750(9) Uani 1 1 d . . . H1A H 0.6445 0.1995 0.2891 0.098 Uiso 1 1 calc R . . H1B H 0.7496 0.3015 0.3538 0.098 Uiso 1 1 calc R . . C2 C 0.7693(4) 0.3610(4) 0.2622(2) 0.0918(11) Uani 1 1 d . . . H2C H 0.7535 0.3183 0.2124 0.119 Uiso 1 1 calc R . . H2D H 0.8771 0.4146 0.2742 0.119 Uiso 1 1 calc R . . C3 C 0.6436(5) 0.4507(5) 0.2779(3) 0.1253(17) Uani 1 1 d . . . H3E H 0.5364 0.3963 0.2647 0.163 Uiso 1 1 calc R . . H3F H 0.6571 0.4891 0.3281 0.163 Uiso 1 1 calc R . . C4 C 0.6577(6) 0.5583(6) 0.2403(3) 0.143(2) Uani 1 1 d . . . H4C H 0.6328 0.5210 0.1905 0.186 Uiso 1 1 calc R . . H4D H 0.7656 0.6090 0.2508 0.186 Uiso 1 1 calc R . . H4E H 0.5838 0.6155 0.2549 0.186 Uiso 1 1 calc R . . C5 C 1.0444(3) 0.2519(3) 0.32756(15) 0.0665(8) Uani 1 1 d . . . H5C H 1.1200 0.1919 0.3280 0.086 Uiso 1 1 calc R . . H5D H 1.0708 0.3035 0.2930 0.086 Uiso 1 1 calc R . . C6 C 1.0689(4) 0.3470(4) 0.39945(19) 0.0901(11) Uani 1 1 d . . . H6C H 0.9968 0.4100 0.3997 0.117 Uiso 1 1 calc R . . H6D H 1.0442 0.2973 0.4349 0.117 Uiso 1 1 calc R . . C7 C 1.2417(4) 0.4214(5) 0.4163(2) 0.1076(14) Uani 1 1 d . . . H7C H 1.3122 0.3574 0.4170 0.140 Uiso 1 1 calc R . . H7D H 1.2664 0.4667 0.3791 0.140 Uiso 1 1 calc R . . C8 C 1.2751(6) 0.5180(6) 0.4827(3) 0.159(2) Uani 1 1 d . . . H8A H 1.2370 0.4768 0.5189 0.207 Uiso 1 1 calc R . . H8B H 1.2216 0.5909 0.4794 0.207 Uiso 1 1 calc R . . H8C H 1.3892 0.5506 0.4940 0.207 Uiso 1 1 calc R . . C9 C 0.8309(3) 0.0759(3) 0.35138(16) 0.0710(9) Uani 1 1 d . . . H9A H 0.7238 0.0241 0.3333 0.092 Uiso 1 1 calc R . . H9B H 0.8251 0.1302 0.3974 0.092 Uiso 1 1 calc R . . C10 C 0.9419(4) -0.0200(4) 0.36104(19) 0.0839(10) Uani 1 1 d . . . H10A H 1.0470 0.0295 0.3842 0.109 Uiso 1 1 calc R . . H10B H 0.9552 -0.0718 0.3155 0.109 Uiso 1 1 calc R . . C11 C 0.8715(5) -0.1131(4) 0.4053(2) 0.0964(11) Uani 1 1 d . . . H11A H 0.8524 -0.0599 0.4495 0.125 Uiso 1 1 calc R . . H11B H 0.7684 -0.1643 0.3808 0.125 Uiso 1 1 calc R . . C12 C 0.9764(6) -0.2065(5) 0.4205(2) 0.1296(17) Uani 1 1 d . . . H12A H 1.0859 -0.1704 0.4168 0.168 Uiso 1 1 calc R . . H12B H 0.9421 -0.2908 0.3874 0.168 Uiso 1 1 calc R . . H12C H 0.9692 -0.2189 0.4674 0.168 Uiso 1 1 calc R . . C13 C 0.8784(4) 0.0913(4) 0.22895(15) 0.0731(9) Uani 1 1 d . . . H13A H 0.9578 0.0347 0.2303 0.095 Uiso 1 1 calc R . . H13B H 0.9140 0.1545 0.2012 0.095 Uiso 1 1 calc R . . C14 C 0.7193(4) 0.0051(4) 0.19184(18) 0.0920(12) Uani 1 1 d . . . H14A H 0.6770 -0.0533 0.2210 0.120 Uiso 1 1 calc R . . H14B H 0.6421 0.0614 0.1847 0.120 Uiso 1 1 calc R . . C15 C 0.7418(5) -0.0783(5) 0.12100(19) 0.0993(13) Uani 1 1 d . . . H15A H 0.6371 -0.1105 0.0927 0.129 Uiso 1 1 calc R . . H15B H 0.8062 -0.0209 0.0969 0.129 Uiso 1 1 calc R . . C16 C 0.8197(6) -0.1944(5) 0.1246(2) 0.1185(15) Uani 1 1 d . . . H16A H 0.7566 -0.2528 0.1478 0.154 Uiso 1 1 calc R . . H16B H 0.9258 -0.1636 0.1505 0.154 Uiso 1 1 calc R . . H16C H 0.8270 -0.2417 0.0778 0.154 Uiso 1 1 calc R . . C17 C 0.4354(3) 0.7011(3) -0.02580(14) 0.0550(7) Uani 1 1 d . . . C18 C 0.0600(3) 0.3951(3) 0.11870(16) 0.0602(7) Uani 1 1 d . . . C19 C 0.2726(3) 0.0043(3) 0.14747(13) 0.0508(7) Uani 1 1 d . . . C20 C 0.3983(3) 0.0055(3) 0.35458(14) 0.0575(7) Uani 1 1 d . . . C21 C 0.4495(3) 0.0016(3) 0.43009(13) 0.0490(6) Uani 1 1 d . . . C22 C 0.4911(3) 0.1187(3) 0.48135(14) 0.0586(7) Uani 1 1 d . . . H22 H 0.4858 0.1996 0.4694 0.076 Uiso 1 1 calc R . . C23 C 0.4591(4) -0.1167(3) 0.44941(14) 0.0626(8) Uani 1 1 d . . . H23 H 0.4318 -0.1964 0.4155 0.081 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 0.0647(4) 0.0628(5) 0.0671(5) 0.0220(4) 0.0171(4) 0.0196(3) S2 0.0697(5) 0.0795(6) 0.0602(5) 0.0100(4) 0.0037(4) 0.0176(4) S3 0.0743(5) 0.0714(5) 0.0413(4) 0.0161(3) 0.0044(3) 0.0220(4) O1 0.153(2) 0.0794(16) 0.0416(11) 0.0096(11) -0.0139(13) 0.0200(15) O2 0.0975(16) 0.0806(16) 0.0491(11) 0.0215(11) -0.0026(11) 0.0207(12) O3 0.128(2) 0.113(2) 0.146(3) -0.019(2) 0.026(2) 0.0094(18) N1 0.0446(12) 0.0898(18) 0.0556(13) 0.0192(13) 0.0085(10) 0.0049(12) N2 0.0846(17) 0.0829(18) 0.0849(18) 0.0383(15) 0.0372(15) 0.0383(15) N3 0.0683(15) 0.0701(17) 0.0723(16) 0.0303(14) 0.0183(13) 0.0204(12) N4 0.0679(15) 0.0771(18) 0.0741(17) 0.0040(15) -0.0065(13) 0.0218(13) N5 0.0772(17) 0.0774(18) 0.0852(19) 0.0119(15) 0.0052(15) 0.0270(14) N6 0.0849(17) 0.0738(17) 0.0455(13) 0.0165(12) 0.0010(12) 0.0233(14) N7 0.0835(16) 0.0762(17) 0.0424(12) 0.0135(12) 0.0022(12) 0.0312(13) C1 0.0499(16) 0.098(2) 0.076(2) 0.0211(19) 0.0076(15) 0.0109(16) C2 0.072(2) 0.110(3) 0.097(3) 0.040(2) 0.0049(19) 0.013(2) C3 0.075(2) 0.141(4) 0.181(5) 0.086(4) 0.009(3) 0.022(3) C4 0.116(4) 0.146(5) 0.167(5) 0.046(4) -0.014(4) 0.026(3) C5 0.0458(14) 0.087(2) 0.0613(17) 0.0164(16) 0.0059(13) 0.0003(14) C6 0.073(2) 0.108(3) 0.073(2) 0.004(2) 0.0080(17) -0.0068(19) C7 0.075(2) 0.109(3) 0.112(3) -0.014(3) -0.011(2) 0.007(2) C8 0.125(4) 0.135(4) 0.176(6) -0.014(4) -0.012(4) -0.011(3) C9 0.0570(16) 0.093(2) 0.0615(18) 0.0213(17) 0.0127(14) 0.0034(16) C10 0.074(2) 0.104(3) 0.080(2) 0.037(2) 0.0176(18) 0.0123(19) C11 0.100(3) 0.107(3) 0.088(3) 0.038(2) 0.023(2) 0.014(2) C12 0.156(4) 0.143(4) 0.102(3) 0.052(3) 0.024(3) 0.030(4) C13 0.0637(17) 0.099(2) 0.0524(16) 0.0133(17) 0.0074(14) 0.0092(17) C14 0.0598(19) 0.122(3) 0.075(2) 0.003(2) -0.0110(17) 0.0005(19) C15 0.097(3) 0.119(3) 0.070(2) 0.012(2) -0.013(2) 0.011(2) C16 0.131(4) 0.107(3) 0.106(3) 0.015(3) -0.006(3) 0.018(3) C17 0.0560(15) 0.0629(18) 0.0482(14) 0.0156(14) 0.0018(12) 0.0166(13) C18 0.0544(15) 0.0680(19) 0.0627(17) 0.0181(16) 0.0162(13) 0.0159(14) C19 0.0467(13) 0.0656(18) 0.0441(14) 0.0169(14) 0.0067(11) 0.0158(12) C20 0.0510(15) 0.075(2) 0.0447(15) 0.0174(16) 0.0001(12) 0.0059(14) C21 0.0425(13) 0.0648(17) 0.0384(13) 0.0139(13) 0.0033(10) 0.0052(12) C22 0.0707(17) 0.0563(17) 0.0484(15) 0.0160(13) 0.0005(13) 0.0106(14) C23 0.0782(19) 0.0612(18) 0.0429(14) 0.0094(13) -0.0017(13) 0.0067(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 S1 C17 1.698(3) . ? S2 C18 1.697(3) . ? S3 C19 1.717(3) . ? O1 C20 1.253(3) . ? O2 C20 1.241(4) . ? N1 C9 1.510(4) . ? N1 C13 1.518(4) . ? N1 C1 1.521(4) . ? N1 C5 1.529(3) . ? N2 C17 1.314(4) . ? N3 C17 1.326(4) . ? N4 C18 1.323(3) . ? N5 C18 1.330(4) . ? N6 C19 1.307(4) . ? N7 C19 1.317(3) . ? C1 C2 1.512(5) . ? C2 C3 1.545(6) . ? C3 C4 1.464(7) . ? C5 C6 1.518(4) . ? C6 C7 1.514(5) . ? C7 C8 1.440(6) . ? C9 C10 1.513(5) . ? C10 C11 1.522(5) . ? C11 C12 1.482(6) . ? C13 C14 1.517(4) . ? C14 C15 1.524(5) . ? C15 C16 1.486(6) . ? C20 C21 1.513(4) . ? C21 C23 1.378(4) . ? C21 C22 1.380(4) . ? C22 C23 1.388(4) 2_656 ? C23 C22 1.388(4) 2_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C13 111.7(2) . . ? C9 N1 C1 106.4(2) . . ? C13 N1 C1 111.1(2) . . ? C9 N1 C5 111.4(2) . . ? C13 N1 C5 105.3(2) . . ? C1 N1 C5 110.9(2) . . ? C2 C1 N1 116.7(3) . . ? C1 C2 C3 108.8(4) . . ? C4 C3 C2 112.7(5) . . ? C6 C5 N1 115.7(2) . . ? C7 C6 C5 109.6(3) . . ? C8 C7 C6 113.7(4) . . ? N1 C9 C10 117.0(2) . . ? C9 C10 C11 109.8(3) . . ? C12 C11 C10 113.6(4) . . ? N1 C13 C14 115.3(3) . . ? C15 C14 C13 110.4(3) . . ? C16 C15 C14 115.2(4) . . ? N2 C17 N3 117.1(3) . . ? N2 C17 S1 121.4(2) . . ? N3 C17 S1 121.4(2) . . ? N4 C18 N5 118.0(3) . . ? N4 C18 S2 121.2(2) . . ? N5 C18 S2 120.8(2) . . ? N6 C19 N7 118.2(2) . . ? N6 C19 S3 121.6(2) . . ? N7 C19 S3 120.2(2) . . ? O2 C20 O1 124.9(3) . . ? O2 C20 C21 117.7(3) . . ? O1 C20 C21 117.4(3) . . ? C23 C21 C22 118.4(2) . . ? C23 C21 C20 121.7(2) . . ? C22 C21 C20 120.0(3) . . ? C21 C22 C23 120.5(3) . 2_656 ? C21 C23 C22 121.1(3) . 2_656 ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.38 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.291 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.038 #===END data_compound2_k02dmks2 _database_code_CSD 208154 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C126 H260 N18 O16 S6' _chemical_formula_weight 2475.88 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 8.58100(10) _cell_length_b 16.3480(2) _cell_length_c 27.2620(5) _cell_angle_alpha 103.6530(10) _cell_angle_beta 92.6830(10) _cell_angle_gamma 101.4730(10) _cell_volume 3624.35(9) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.134 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1366 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50750 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.0619 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 26.90 _reflns_number_total 14978 _reflns_number_gt 10444 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'Denzo and Scalepack (otwinowski & Minor, 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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 [1.00000+0.00000exp(0.00(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+0.0000+1.6083*P+(0.0464P)^2^+0.0000sin\q/\l] where P = 0.00000Fo^2^ + 1.00000Fc^2^ ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0012(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 14978 _refine_ls_number_parameters 763 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1246 _refine_ls_wR_factor_gt 0.1087 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.16758(6) -0.23161(3) 0.271072(19) 0.03219(13) Uani 1 1 d . . . S2 S 0.40165(7) -0.02463(3) 0.41676(2) 0.04021(15) Uani 1 1 d . . . S3 S 1.22959(7) 0.66413(3) 0.10411(2) 0.03614(14) Uani 1 1 d . . . O1 O 0.94013(15) 0.40726(8) 0.17684(5) 0.0290(3) Uani 1 1 d . . . O2 O 0.87485(16) 0.34601(8) 0.09417(5) 0.0334(3) Uani 1 1 d . . . O3 O 0.46503(17) -0.02872(8) 0.15609(5) 0.0378(3) Uani 1 1 d . . . O4 O 0.57664(19) 0.02687(9) 0.23571(6) 0.0445(4) Uani 1 1 d . . . O5 O 0.18678(18) -0.34685(8) 0.42954(5) 0.0376(3) Uani 1 1 d . . . O6 O 0.19934(18) -0.27475(8) 0.51048(5) 0.0399(4) Uani 1 1 d . . . O7 O 0.3398(3) -0.36422(12) 0.33144(8) 0.0716(6) Uani 1 1 d D . . O8 O 1.0069(2) 0.67844(12) 0.00235(6) 0.0499(4) Uani 1 1 d D . . N1 N 0.25193(19) 0.21919(10) 0.46222(6) 0.0326(4) Uani 1 1 d . . . N2 N 0.45619(18) 0.43394(10) 0.19863(6) 0.0267(3) Uani 1 1 d . . . N3 N 0.89917(18) 0.88701(9) 0.13045(6) 0.0257(3) Uani 1 1 d . . . N4 N 0.30348(19) -0.15839(10) 0.20225(6) 0.0288(4) Uani 1 1 d . . . H4A H 0.3618 -0.1157 0.1923 0.035 Uiso 1 1 calc R . . H4B H 0.2574 -0.2064 0.1798 0.035 Uiso 1 1 calc R . . N5 N 0.3573(2) -0.07617(10) 0.28325(6) 0.0349(4) Uani 1 1 d . . . H5A H 0.4146 -0.0350 0.2718 0.042 Uiso 1 1 calc R . . H5B H 0.3479 -0.0682 0.3160 0.042 Uiso 1 1 calc R . . N6 N 0.3455(2) -0.12079(10) 0.48287(6) 0.0341(4) Uani 1 1 d . . . H6A H 0.3038 -0.1686 0.4913 0.041 Uiso 1 1 calc R . . H6B H 0.4016 -0.0763 0.5060 0.041 Uiso 1 1 calc R . . N7 N 0.2383(2) -0.18544(10) 0.40242(6) 0.0401(4) Uani 1 1 d . . . H7A H 0.1991 -0.2317 0.4128 0.048 Uiso 1 1 calc R . . H7B H 0.2206 -0.1854 0.3704 0.048 Uiso 1 1 calc R . . N8 N 1.1013(2) 0.49721(10) 0.08661(6) 0.0331(4) Uani 1 1 d . . . H8A H 1.0521 0.4512 0.0956 0.040 Uiso 1 1 calc R . . H8B H 1.1309 0.4925 0.0558 0.040 Uiso 1 1 calc R . . N9 N 1.0828(2) 0.57642(10) 0.16575(6) 0.0330(4) Uani 1 1 d . . . H9A H 1.0341 0.5285 0.1729 0.040 Uiso 1 1 calc R . . H9B H 1.0997 0.6257 0.1890 0.040 Uiso 1 1 calc R . . C1 C 0.4011(2) 0.21012(13) 0.43515(8) 0.0333(5) Uani 1 1 d . . . H1A H 0.4928 0.2223 0.4611 0.040 Uiso 1 1 calc R . . H1B H 0.3872 0.1494 0.4157 0.040 Uiso 1 1 calc R . . C2 C 0.4429(3) 0.26711(14) 0.39946(8) 0.0382(5) Uani 1 1 d . . . H2A H 0.4712 0.3282 0.4190 0.046 Uiso 1 1 calc R . . H2B H 0.3491 0.2597 0.3750 0.046 Uiso 1 1 calc R . . C3 C 0.5831(2) 0.24444(14) 0.37082(8) 0.0401(5) Uani 1 1 d . . . H3A H 0.6729 0.2463 0.3955 0.048 Uiso 1 1 calc R . . H3B H 0.5509 0.1849 0.3491 0.048 Uiso 1 1 calc R . . C4 C 0.6384(3) 0.30556(16) 0.33824(9) 0.0504(6) Uani 1 1 d . . . H4C H 0.7286 0.2889 0.3206 0.076 Uiso 1 1 calc R . . H4D H 0.6720 0.3644 0.3597 0.076 Uiso 1 1 calc R . . H4E H 0.5504 0.3029 0.3133 0.076 Uiso 1 1 calc R . . C5 C 0.2438(2) 0.15952(14) 0.49756(8) 0.0369(5) Uani 1 1 d . . . H5C H 0.2443 0.1009 0.4770 0.044 Uiso 1 1 calc R . . H5D H 0.3423 0.1788 0.5213 0.044 Uiso 1 1 calc R . . C6 C 0.1020(3) 0.15315(17) 0.52845(10) 0.0540(6) Uani 1 1 d . . . H6C H 0.0031 0.1236 0.5059 0.065 Uiso 1 1 calc R . . H6D H 0.0901 0.2116 0.5460 0.065 Uiso 1 1 calc R . . C7 C 0.1286(4) 0.10231(18) 0.56741(11) 0.0639(8) Uani 1 1 d . . . H7C H 0.0270 0.0866 0.5822 0.077 Uiso 1 1 calc R . . H7D H 0.1587 0.0482 0.5499 0.077 Uiso 1 1 calc R . . C8 C 0.2578(5) 0.1521(2) 0.61009(11) 0.0879(11) Uani 1 1 d . . . H8C H 0.2698 0.1164 0.6337 0.132 Uiso 1 1 calc R . . H8D H 0.2274 0.2051 0.6282 0.132 Uiso 1 1 calc R . . H8E H 0.3593 0.1669 0.5958 0.132 Uiso 1 1 calc R . . C9 C 0.2616(2) 0.31178(13) 0.49127(8) 0.0345(5) Uani 1 1 d . . . H9C H 0.2643 0.3475 0.4665 0.041 Uiso 1 1 calc R . . H9D H 0.1625 0.3143 0.5082 0.041 Uiso 1 1 calc R . . C10 C 0.4023(2) 0.35187(13) 0.53077(8) 0.0390(5) Uani 1 1 d . . . H10A H 0.5030 0.3507 0.5146 0.047 Uiso 1 1 calc R . . H10B H 0.4001 0.3182 0.5566 0.047 Uiso 1 1 calc R . . C11 C 0.3964(3) 0.44485(13) 0.55623(9) 0.0414(5) Uani 1 1 d . . . H11A H 0.3973 0.4780 0.5301 0.050 Uiso 1 1 calc R . . H11B H 0.2952 0.4455 0.5722 0.050 Uiso 1 1 calc R . . C12 C 0.5354(3) 0.48812(15) 0.59609(10) 0.0516(6) Uani 1 1 d . . . H12A H 0.5266 0.5474 0.6114 0.077 Uiso 1 1 calc R . . H12B H 0.6358 0.4888 0.5803 0.077 Uiso 1 1 calc R . . H12C H 0.5338 0.4562 0.6224 0.077 Uiso 1 1 calc R . . C13 C 0.1024(2) 0.19447(14) 0.42496(8) 0.0383(5) Uani 1 1 d . . . H13A H 0.0088 0.1982 0.4446 0.046 Uiso 1 1 calc R . . H13B H 0.1093 0.2376 0.4046 0.046 Uiso 1 1 calc R . . C14 C 0.0724(3) 0.10552(15) 0.38880(9) 0.0491(6) Uani 1 1 d . . . H14A H 0.0693 0.0616 0.4085 0.059 Uiso 1 1 calc R . . H14B H 0.1610 0.1021 0.3670 0.059 Uiso 1 1 calc R . . C15 C -0.0845(3) 0.0868(2) 0.35584(10) 0.0672(8) Uani 1 1 d . . . H15A H -0.1733 0.0861 0.3778 0.081 Uiso 1 1 calc R . . H15B H -0.0843 0.1338 0.3386 0.081 Uiso 1 1 calc R . . C16 C -0.1136(5) 0.0026(2) 0.31666(13) 0.1032(13) Uani 1 1 d . . . H16A H -0.2158 -0.0060 0.2965 0.155 Uiso 1 1 calc R . . H16B H -0.1168 -0.0444 0.3335 0.155 Uiso 1 1 calc R . . H16C H -0.0272 0.0032 0.2944 0.155 Uiso 1 1 calc R . . C17 C 0.3178(2) 0.44970(12) 0.23008(7) 0.0277(4) Uani 1 1 d . . . H17A H 0.3440 0.5102 0.2506 0.033 Uiso 1 1 calc R . . H17B H 0.2217 0.4429 0.2067 0.033 Uiso 1 1 calc R . . C18 C 0.2772(2) 0.39122(13) 0.26516(8) 0.0336(5) Uani 1 1 d . . . H18A H 0.3730 0.3961 0.2883 0.040 Uiso 1 1 calc R . . H18B H 0.2442 0.3307 0.2450 0.040 Uiso 1 1 calc R . . C19 C 0.1427(2) 0.41528(12) 0.29623(7) 0.0314(4) Uani 1 1 d . . . H19A H 0.1794 0.4742 0.3184 0.038 Uiso 1 1 calc R . . H19B H 0.0506 0.4156 0.2730 0.038 Uiso 1 1 calc R . . C20 C 0.0893(3) 0.35315(14) 0.32856(8) 0.0403(5) Uani 1 1 d . . . H20A H 0.0024 0.3706 0.3477 0.060 Uiso 1 1 calc R . . H20B H 0.1794 0.3539 0.3522 0.060 Uiso 1 1 calc R . . H20C H 0.0517 0.2948 0.3067 0.060 Uiso 1 1 calc R . . C21 C 0.4698(2) 0.49529(12) 0.16418(7) 0.0292(4) Uani 1 1 d . . . H21A H 0.3702 0.4796 0.1410 0.035 Uiso 1 1 calc R . . H21B H 0.4767 0.5543 0.1855 0.035 Uiso 1 1 calc R . . C22 C 0.6104(2) 0.49726(13) 0.13231(8) 0.0317(4) Uani 1 1 d . . . H22A H 0.6188 0.4376 0.1160 0.038 Uiso 1 1 calc R . . H22B H 0.7106 0.5265 0.1543 0.038 Uiso 1 1 calc R . . C23 C 0.5874(2) 0.54518(14) 0.09171(8) 0.0376(5) Uani 1 1 d . . . H23A H 0.4895 0.5141 0.0690 0.045 Uiso 1 1 calc R . . H23B H 0.5724 0.6035 0.1082 0.045 Uiso 1 1 calc R . . C24 C 0.7287(3) 0.55334(14) 0.06021(9) 0.0419(5) Uani 1 1 d . . . H24A H 0.7087 0.5843 0.0347 0.063 Uiso 1 1 calc R . . H24B H 0.7430 0.4957 0.0433 0.063 Uiso 1 1 calc R . . H24C H 0.8256 0.5853 0.0824 0.063 Uiso 1 1 calc R . . C25 C 0.6111(2) 0.44917(12) 0.23234(7) 0.0282(4) Uani 1 1 d . . . H25A H 0.5978 0.4067 0.2532 0.034 Uiso 1 1 calc R . . H25B H 0.6968 0.4376 0.2103 0.034 Uiso 1 1 calc R . . C26 C 0.6659(2) 0.53871(12) 0.26753(8) 0.0312(4) Uani 1 1 d . . . H26A H 0.5801 0.5525 0.2890 0.037 Uiso 1 1 calc R . . H26B H 0.6885 0.5819 0.2473 0.037 Uiso 1 1 calc R . . C27 C 0.8158(3) 0.54270(14) 0.30094(9) 0.0423(5) Uani 1 1 d . . . H27A H 0.7935 0.4976 0.3199 0.051 Uiso 1 1 calc R . . H27B H 0.9018 0.5305 0.2792 0.051 Uiso 1 1 calc R . . C28 C 0.8730(3) 0.63014(15) 0.33844(9) 0.0491(6) Uani 1 1 d . . . H28A H 0.9691 0.6297 0.3592 0.074 Uiso 1 1 calc R . . H28B H 0.7889 0.6421 0.3605 0.074 Uiso 1 1 calc R . . H28C H 0.8977 0.6749 0.3199 0.074 Uiso 1 1 calc R . . C29 C 0.4258(2) 0.34087(11) 0.16765(7) 0.0279(4) Uani 1 1 d . . . H29A H 0.5138 0.3348 0.1458 0.033 Uiso 1 1 calc R . . H29B H 0.4310 0.3037 0.1913 0.033 Uiso 1 1 calc R . . C30 C 0.2691(2) 0.30678(12) 0.13438(8) 0.0315(4) Uani 1 1 d . . . H30A H 0.2603 0.3435 0.1106 0.038 Uiso 1 1 calc R . . H30B H 0.1789 0.3086 0.1557 0.038 Uiso 1 1 calc R . . C31 C 0.2605(2) 0.21425(12) 0.10449(8) 0.0306(4) Uani 1 1 d . . . H31A H 0.3522 0.2129 0.0838 0.037 Uiso 1 1 calc R . . H31B H 0.2695 0.1781 0.1285 0.037 Uiso 1 1 calc R . . C32 C 0.1071(3) 0.17675(13) 0.07015(9) 0.0414(5) Uani 1 1 d . . . H32A H 0.1069 0.1174 0.0518 0.062 Uiso 1 1 calc R . . H32B H 0.0987 0.2116 0.0458 0.062 Uiso 1 1 calc R . . H32C H 0.0160 0.1769 0.0905 0.062 Uiso 1 1 calc R . . C33 C 0.8796(2) 0.82343(12) 0.16370(7) 0.0278(4) Uani 1 1 d . . . H33A H 0.8793 0.7655 0.1421 0.033 Uiso 1 1 calc R . . H33B H 0.9741 0.8397 0.1890 0.033 Uiso 1 1 calc R . . C34 C 0.7305(2) 0.81750(12) 0.19166(8) 0.0316(4) Uani 1 1 d . . . H34A H 0.6344 0.7950 0.1669 0.038 Uiso 1 1 calc R . . H34B H 0.7245 0.8756 0.2118 0.038 Uiso 1 1 calc R . . C35 C 0.7354(3) 0.75784(14) 0.22667(9) 0.0388(5) Uani 1 1 d . . . H35A H 0.7463 0.7007 0.2065 0.047 Uiso 1 1 calc R . . H35B H 0.8303 0.7817 0.2518 0.047 Uiso 1 1 calc R . . C36 C 0.5865(3) 0.74675(15) 0.25440(9) 0.0439(6) Uani 1 1 d . . . H36A H 0.5940 0.7075 0.2762 0.066 Uiso 1 1 calc R . . H36B H 0.4923 0.7227 0.2297 0.066 Uiso 1 1 calc R . . H36C H 0.5771 0.8029 0.2753 0.066 Uiso 1 1 calc R . . C37 C 1.0406(2) 0.87235(12) 0.10043(7) 0.0268(4) Uani 1 1 d . . . H37A H 1.1339 0.8775 0.1246 0.032 Uiso 1 1 calc R . . H37B H 1.0150 0.8126 0.0788 0.032 Uiso 1 1 calc R . . C38 C 1.0876(2) 0.93329(12) 0.06711(7) 0.0303(4) Uani 1 1 d . . . H38A H 1.1161 0.9933 0.0882 0.036 Uiso 1 1 calc R . . H38B H 0.9960 0.9285 0.0424 0.036 Uiso 1 1 calc R . . C39 C 1.2292(2) 0.91216(13) 0.03890(8) 0.0320(4) Uani 1 1 d . . . H39A H 1.3206 0.9173 0.0638 0.038 Uiso 1 1 calc R . . H39B H 1.2006 0.8518 0.0183 0.038 Uiso 1 1 calc R . . C40 C 1.2786(3) 0.97149(14) 0.00464(8) 0.0388(5) Uani 1 1 d . . . H40A H 1.3701 0.9560 -0.0127 0.058 Uiso 1 1 calc R . . H40B H 1.3086 1.0313 0.0250 0.058 Uiso 1 1 calc R . . H40C H 1.1892 0.9656 -0.0206 0.058 Uiso 1 1 calc R . . C41 C 0.9286(2) 0.97931(11) 0.16267(7) 0.0276(4) Uani 1 1 d . . . H41A H 0.9208 1.0176 0.1399 0.033 Uiso 1 1 calc R . . H41B H 0.8420 0.9838 0.1853 0.033 Uiso 1 1 calc R . . C42 C 1.0875(2) 1.01271(12) 0.19513(8) 0.0344(5) Uani 1 1 d . . . H42A H 1.1760 1.0087 0.1733 0.041 Uiso 1 1 calc R . . H42B H 1.0957 0.9769 0.2194 0.041 Uiso 1 1 calc R . . C43 C 1.1017(2) 1.10631(12) 0.22419(8) 0.0335(5) Uani 1 1 d . . . H43A H 1.0928 1.1418 0.1998 0.040 Uiso 1 1 calc R . . H43B H 1.0125 1.1100 0.2458 0.040 Uiso 1 1 calc R . . C44 C 1.2590(3) 1.14211(14) 0.25717(9) 0.0487(6) Uani 1 1 d . . . H44A H 1.2640 1.2022 0.2751 0.073 Uiso 1 1 calc R . . H44B H 1.3476 1.1394 0.2358 0.073 Uiso 1 1 calc R . . H44C H 1.2672 1.1079 0.2819 0.073 Uiso 1 1 calc R . . C45 C 0.7475(2) 0.87284(12) 0.09532(7) 0.0269(4) Uani 1 1 d . . . H45A H 0.6604 0.8860 0.1163 0.032 Uiso 1 1 calc R . . H45B H 0.7654 0.9145 0.0739 0.032 Uiso 1 1 calc R . . C46 C 0.6925(2) 0.78287(12) 0.06085(7) 0.0305(4) Uani 1 1 d . . . H46A H 0.6697 0.7405 0.0816 0.037 Uiso 1 1 calc R . . H46B H 0.7785 0.7684 0.0396 0.037 Uiso 1 1 calc R . . C47 C 0.5428(2) 0.77746(13) 0.02690(8) 0.0346(5) Uani 1 1 d . . . H47A H 0.4568 0.7910 0.0484 0.042 Uiso 1 1 calc R . . H47B H 0.5655 0.8212 0.0070 0.042 Uiso 1 1 calc R . . C48 C 0.4851(3) 0.68887(13) -0.00929(8) 0.0393(5) Uani 1 1 d . . . H48A H 0.3889 0.6884 -0.0303 0.059 Uiso 1 1 calc R . . H48B H 0.4602 0.6455 0.0102 0.059 Uiso 1 1 calc R . . H48C H 0.5689 0.6756 -0.0311 0.059 Uiso 1 1 calc R . . C49 C 0.8753(2) 0.34493(11) 0.14015(7) 0.0241(4) Uani 1 1 d . . . C50 C 0.7898(2) 0.26281(11) 0.15264(7) 0.0234(4) Uani 1 1 d . . . C51 C 0.7013(2) 0.19339(11) 0.11505(7) 0.0264(4) Uani 1 1 d . . . H51 H 0.6951 0.1970 0.0808 0.032 Uiso 1 1 calc R . . C52 C 0.6226(2) 0.11936(12) 0.12717(7) 0.0282(4) Uani 1 1 d . . . H52 H 0.5611 0.0732 0.1012 0.034 Uiso 1 1 calc R . . C54 C 0.6325(2) 0.11181(11) 0.17696(7) 0.0252(4) Uani 1 1 d . . . C55 C 0.7211(2) 0.18060(12) 0.21417(7) 0.0301(4) Uani 1 1 d . . . H55 H 0.7294 0.1763 0.2483 0.036 Uiso 1 1 calc R . . C56 C 0.7978(2) 0.25551(12) 0.20241(7) 0.0278(4) Uani 1 1 d . . . H56 H 0.8563 0.3023 0.2286 0.033 Uiso 1 1 calc R . . C57 C 0.5499(2) 0.02986(12) 0.19071(8) 0.0298(4) Uani 1 1 d . . . C58 C 0.1617(2) -0.34184(12) 0.47510(7) 0.0267(4) Uani 1 1 d . . . C59 C 0.0787(2) -0.42423(11) 0.48803(7) 0.0235(4) Uani 1 1 d . . . C60 C 0.0235(2) -0.49971(12) 0.45033(7) 0.0278(4) Uani 1 1 d . . . H60 H 0.0395 -0.5001 0.4160 0.033 Uiso 1 1 calc R . . C61 C 0.0548(2) -0.42539(12) 0.53809(7) 0.0287(4) Uani 1 1 d . . . H61 H 0.0923 -0.3745 0.5645 0.034 Uiso 1 1 calc R . . C62 C 0.2848(2) -0.15025(11) 0.25121(7) 0.0260(4) Uani 1 1 d . . . C63 C 0.3240(2) -0.11582(12) 0.43503(7) 0.0304(4) Uani 1 1 d . . . C64 C 1.1311(2) 0.57437(11) 0.11989(7) 0.0269(4) Uani 1 1 d . . . HW8A H 1.071(3) 0.6678(17) 0.0233(9) 0.061(8) Uiso 1 1 d D . . HW8B H 1.065(3) 0.6782(18) -0.0229(9) 0.072(9) Uiso 1 1 d D . . HW7B H 0.293(4) -0.356(2) 0.3645(9) 0.108 Uiso 1 1 d D . . HW7A H 0.316(4) -0.3175(17) 0.3165(12) 0.108 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0289(3) 0.0335(3) 0.0342(3) 0.0149(2) 0.0037(2) -0.0009(2) S2 0.0605(4) 0.0251(3) 0.0322(3) 0.0119(2) 0.0003(3) -0.0021(2) S3 0.0447(3) 0.0271(3) 0.0355(3) 0.0121(2) 0.0066(2) -0.0005(2) O1 0.0305(7) 0.0248(7) 0.0304(7) 0.0089(6) 0.0032(6) 0.0007(6) O2 0.0423(8) 0.0316(7) 0.0268(8) 0.0130(6) 0.0051(6) 0.0015(6) O3 0.0430(8) 0.0261(7) 0.0401(9) 0.0076(7) 0.0102(7) -0.0028(6) O4 0.0528(10) 0.0388(8) 0.0409(9) 0.0214(7) 0.0006(7) -0.0048(7) O5 0.0500(9) 0.0297(7) 0.0321(8) 0.0128(6) 0.0061(7) -0.0002(6) O6 0.0562(10) 0.0234(7) 0.0349(8) 0.0079(6) 0.0072(7) -0.0046(7) O7 0.0989(16) 0.0593(12) 0.0757(14) 0.0309(11) 0.0366(12) 0.0382(11) O8 0.0554(11) 0.0653(11) 0.0351(10) 0.0151(9) 0.0117(9) 0.0222(9) N1 0.0286(9) 0.0346(9) 0.0387(10) 0.0165(8) 0.0031(7) 0.0076(7) N2 0.0252(8) 0.0261(8) 0.0310(9) 0.0092(7) 0.0036(7) 0.0081(7) N3 0.0256(8) 0.0243(8) 0.0291(9) 0.0077(7) 0.0047(7) 0.0082(7) N4 0.0322(9) 0.0235(8) 0.0295(9) 0.0109(7) 0.0009(7) -0.0014(7) N5 0.0453(10) 0.0283(9) 0.0300(9) 0.0103(7) 0.0070(8) 0.0006(8) N6 0.0425(10) 0.0269(8) 0.0297(9) 0.0121(7) -0.0031(8) -0.0042(7) N7 0.0584(12) 0.0277(9) 0.0287(9) 0.0111(8) -0.0018(8) -0.0074(8) N8 0.0387(10) 0.0250(8) 0.0340(9) 0.0083(7) 0.0048(8) 0.0021(7) N9 0.0397(10) 0.0246(8) 0.0339(10) 0.0106(7) 0.0063(8) 0.0007(7) C1 0.0299(11) 0.0340(11) 0.0393(12) 0.0127(9) 0.0052(9) 0.0097(9) C2 0.0349(11) 0.0389(12) 0.0439(13) 0.0142(10) 0.0072(10) 0.0098(9) C3 0.0319(11) 0.0451(13) 0.0396(12) 0.0055(10) 0.0032(9) 0.0059(10) C4 0.0377(13) 0.0633(16) 0.0473(14) 0.0134(12) 0.0121(11) 0.0032(11) C5 0.0368(12) 0.0383(11) 0.0411(12) 0.0205(10) 0.0040(10) 0.0083(9) C6 0.0505(15) 0.0636(16) 0.0617(16) 0.0389(14) 0.0169(12) 0.0145(13) C7 0.0782(19) 0.0645(17) 0.0649(18) 0.0417(15) 0.0231(15) 0.0187(15) C8 0.138(3) 0.086(2) 0.0505(18) 0.0324(17) 0.0063(19) 0.033(2) C9 0.0317(11) 0.0345(11) 0.0432(12) 0.0156(10) 0.0072(9) 0.0131(9) C10 0.0326(11) 0.0410(12) 0.0447(13) 0.0107(10) 0.0019(10) 0.0113(10) C11 0.0432(13) 0.0385(12) 0.0470(13) 0.0153(10) 0.0084(10) 0.0131(10) C12 0.0534(15) 0.0429(13) 0.0548(15) 0.0058(12) 0.0040(12) 0.0098(12) C13 0.0272(10) 0.0482(13) 0.0429(13) 0.0230(11) -0.0014(9) 0.0034(9) C14 0.0466(14) 0.0489(14) 0.0490(14) 0.0199(12) -0.0061(11) -0.0032(11) C15 0.0528(16) 0.092(2) 0.0450(15) 0.0158(15) -0.0077(13) -0.0072(15) C16 0.113(3) 0.108(3) 0.065(2) 0.036(2) -0.024(2) -0.039(2) C17 0.0246(10) 0.0275(10) 0.0322(11) 0.0059(8) 0.0047(8) 0.0100(8) C18 0.0324(11) 0.0363(11) 0.0362(11) 0.0116(9) 0.0079(9) 0.0129(9) C19 0.0268(10) 0.0320(10) 0.0322(11) 0.0024(9) 0.0030(8) 0.0056(8) C20 0.0354(12) 0.0469(13) 0.0372(12) 0.0084(10) 0.0097(10) 0.0066(10) C21 0.0277(10) 0.0282(10) 0.0346(11) 0.0120(9) 0.0013(8) 0.0084(8) C22 0.0299(10) 0.0324(10) 0.0366(11) 0.0141(9) 0.0040(9) 0.0091(9) C23 0.0332(11) 0.0412(12) 0.0449(13) 0.0209(10) 0.0048(10) 0.0108(9) C24 0.0387(12) 0.0454(13) 0.0492(14) 0.0233(11) 0.0103(10) 0.0119(10) C25 0.0225(9) 0.0302(10) 0.0345(11) 0.0109(9) 0.0020(8) 0.0082(8) C26 0.0283(10) 0.0305(10) 0.0352(11) 0.0089(9) 0.0024(9) 0.0063(8) C27 0.0345(12) 0.0411(12) 0.0513(14) 0.0139(11) -0.0051(10) 0.0072(10) C28 0.0422(13) 0.0464(13) 0.0516(15) 0.0125(12) -0.0089(11) -0.0038(11) C29 0.0277(10) 0.0247(9) 0.0330(11) 0.0070(8) 0.0053(8) 0.0094(8) C30 0.0287(10) 0.0312(10) 0.0343(11) 0.0050(9) 0.0030(9) 0.0096(9) C31 0.0317(10) 0.0280(10) 0.0342(11) 0.0104(9) 0.0051(9) 0.0076(8) C32 0.0390(12) 0.0343(11) 0.0459(13) -0.0006(10) -0.0021(10) 0.0105(10) C33 0.0291(10) 0.0272(10) 0.0311(10) 0.0123(8) 0.0039(8) 0.0092(8) C34 0.0303(10) 0.0314(10) 0.0372(11) 0.0152(9) 0.0060(9) 0.0081(9) C35 0.0367(12) 0.0425(12) 0.0472(13) 0.0245(10) 0.0110(10) 0.0143(10) C36 0.0431(13) 0.0492(13) 0.0557(15) 0.0317(12) 0.0210(11) 0.0217(11) C37 0.0246(9) 0.0254(9) 0.0313(10) 0.0064(8) 0.0051(8) 0.0080(8) C38 0.0299(10) 0.0317(10) 0.0331(11) 0.0111(9) 0.0071(9) 0.0107(9) C39 0.0267(10) 0.0333(11) 0.0349(11) 0.0053(9) 0.0061(9) 0.0075(9) C40 0.0334(11) 0.0430(12) 0.0376(12) 0.0082(10) 0.0108(9) 0.0034(10) C41 0.0282(10) 0.0243(9) 0.0328(11) 0.0083(8) 0.0080(8) 0.0090(8) C42 0.0307(11) 0.0320(11) 0.0392(12) 0.0051(9) 0.0017(9) 0.0089(9) C43 0.0351(11) 0.0283(10) 0.0367(12) 0.0065(9) 0.0045(9) 0.0076(9) C44 0.0452(13) 0.0356(12) 0.0570(15) -0.0029(11) -0.0053(11) 0.0091(11) C45 0.0235(9) 0.0287(10) 0.0314(10) 0.0111(8) 0.0029(8) 0.0080(8) C46 0.0297(10) 0.0308(10) 0.0330(11) 0.0098(9) 0.0026(8) 0.0090(8) C47 0.0307(11) 0.0365(11) 0.0387(12) 0.0133(9) 0.0010(9) 0.0079(9) C48 0.0360(12) 0.0414(12) 0.0378(12) 0.0113(10) -0.0047(9) 0.0023(10) C49 0.0191(9) 0.0265(10) 0.0295(11) 0.0104(8) 0.0043(8) 0.0065(8) C50 0.0202(9) 0.0233(9) 0.0286(10) 0.0077(8) 0.0065(8) 0.0071(7) C51 0.0282(10) 0.0275(10) 0.0245(10) 0.0082(8) 0.0057(8) 0.0056(8) C52 0.0270(10) 0.0245(9) 0.0303(11) 0.0042(8) 0.0038(8) 0.0022(8) C54 0.0225(9) 0.0237(9) 0.0313(11) 0.0086(8) 0.0070(8) 0.0063(8) C55 0.0332(11) 0.0301(10) 0.0283(10) 0.0115(9) 0.0033(8) 0.0050(9) C56 0.0291(10) 0.0248(10) 0.0277(10) 0.0065(8) 0.0007(8) 0.0018(8) C57 0.0275(10) 0.0265(10) 0.0389(12) 0.0122(9) 0.0100(9) 0.0073(8) C58 0.0243(10) 0.0262(10) 0.0317(11) 0.0120(9) 0.0021(8) 0.0048(8) C59 0.0204(9) 0.0229(9) 0.0287(10) 0.0097(8) 0.0026(7) 0.0045(7) C60 0.0324(10) 0.0270(10) 0.0245(10) 0.0087(8) 0.0053(8) 0.0041(8) C61 0.0334(11) 0.0238(9) 0.0265(10) 0.0050(8) 0.0009(8) 0.0024(8) C62 0.0241(9) 0.0258(10) 0.0314(11) 0.0133(8) 0.0020(8) 0.0058(8) C63 0.0345(11) 0.0256(10) 0.0320(11) 0.0104(9) 0.0032(9) 0.0046(8) C64 0.0238(9) 0.0244(10) 0.0346(11) 0.0116(8) 0.0003(8) 0.0056(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C62 1.7128(18) . ? S2 C63 1.7034(19) . ? S3 C64 1.7004(19) . ? O1 C49 1.261(2) . ? O2 C49 1.258(2) . ? O3 C57 1.253(2) . ? O4 C57 1.252(2) . ? O5 C58 1.257(2) . ? O6 C58 1.252(2) . ? N1 C9 1.517(3) . ? N1 C5 1.519(2) . ? N1 C1 1.522(2) . ? N1 C13 1.523(3) . ? N2 C21 1.520(2) . ? N2 C29 1.520(2) . ? N2 C25 1.523(2) . ? N2 C17 1.525(2) . ? N3 C41 1.521(2) . ? N3 C37 1.522(2) . ? N3 C33 1.523(2) . ? N3 C45 1.524(2) . ? N4 C62 1.330(2) . ? N5 C62 1.329(2) . ? N6 C63 1.332(2) . ? N7 C63 1.325(2) . ? N8 C64 1.338(2) . ? N9 C64 1.330(2) . ? C1 C2 1.507(3) . ? C2 C3 1.524(3) . ? C3 C4 1.511(3) . ? C5 C6 1.513(3) . ? C6 C7 1.530(3) . ? C7 C8 1.523(4) . ? C9 C10 1.509(3) . ? C10 C11 1.527(3) . ? C11 C12 1.511(3) . ? C13 C14 1.518(3) . ? C14 C15 1.518(3) . ? C15 C16 1.497(4) . ? C17 C18 1.510(3) . ? C18 C19 1.523(3) . ? C19 C20 1.514(3) . ? C21 C22 1.518(3) . ? C22 C23 1.526(3) . ? C23 C24 1.521(3) . ? C25 C26 1.518(3) . ? C26 C27 1.523(3) . ? C27 C28 1.521(3) . ? C29 C30 1.514(3) . ? C30 C31 1.525(3) . ? C31 C32 1.510(3) . ? C33 C34 1.518(3) . ? C34 C35 1.522(3) . ? C35 C36 1.516(3) . ? C37 C38 1.511(3) . ? C38 C39 1.522(3) . ? C39 C40 1.515(3) . ? C41 C42 1.517(3) . ? C42 C43 1.526(3) . ? C43 C44 1.516(3) . ? C45 C46 1.516(3) . ? C46 C47 1.524(3) . ? C47 C48 1.520(3) . ? C49 C50 1.518(2) . ? C50 C56 1.390(3) . ? C50 C51 1.396(3) . ? C51 C52 1.384(3) . ? C52 C54 1.392(3) . ? C54 C55 1.386(3) . ? C54 C57 1.524(3) . ? C55 C56 1.386(3) . ? C58 C59 1.521(2) . ? C59 C60 1.388(3) . ? C59 C61 1.393(3) . ? C60 C61 1.387(3) 2_546 ? C61 C60 1.387(3) 2_546 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C5 111.52(16) . . ? C9 N1 C1 111.28(15) . . ? C5 N1 C1 105.18(14) . . ? C9 N1 C13 106.08(15) . . ? C5 N1 C13 111.21(15) . . ? C1 N1 C13 111.69(16) . . ? C21 N2 C29 110.78(14) . . ? C21 N2 C25 111.22(14) . . ? C29 N2 C25 106.12(13) . . ? C21 N2 C17 106.49(13) . . ? C29 N2 C17 110.98(14) . . ? C25 N2 C17 111.32(14) . . ? C41 N3 C37 110.87(14) . . ? C41 N3 C33 110.81(14) . . ? C37 N3 C33 106.56(13) . . ? C41 N3 C45 106.64(13) . . ? C37 N3 C45 111.25(14) . . ? C33 N3 C45 110.78(14) . . ? C2 C1 N1 116.17(15) . . ? C1 C2 C3 110.49(17) . . ? C4 C3 C2 112.04(18) . . ? C6 C5 N1 116.77(17) . . ? C5 C6 C7 108.9(2) . . ? C8 C7 C6 113.1(2) . . ? C10 C9 N1 116.32(16) . . ? C9 C10 C11 110.17(17) . . ? C12 C11 C10 112.26(18) . . ? C14 C13 N1 116.02(17) . . ? C13 C14 C15 110.9(2) . . ? C16 C15 C14 113.0(3) . . ? C18 C17 N2 115.25(14) . . ? C17 C18 C19 110.67(15) . . ? C20 C19 C18 112.02(16) . . ? C22 C21 N2 116.19(14) . . ? C21 C22 C23 109.85(16) . . ? C24 C23 C22 112.33(17) . . ? C26 C25 N2 115.81(15) . . ? C25 C26 C27 109.88(16) . . ? C28 C27 C26 112.27(18) . . ? C30 C29 N2 116.51(15) . . ? C29 C30 C31 109.81(15) . . ? C32 C31 C30 112.36(16) . . ? C34 C33 N3 115.81(14) . . ? C33 C34 C35 109.57(16) . . ? C36 C35 C34 112.12(17) . . ? C38 C37 N3 115.25(14) . . ? C37 C38 C39 110.48(15) . . ? C40 C39 C38 111.96(16) . . ? C42 C41 N3 116.08(15) . . ? C41 C42 C43 110.15(16) . . ? C44 C43 C42 111.79(17) . . ? C46 C45 N3 115.36(14) . . ? C45 C46 C47 110.36(15) . . ? C48 C47 C46 112.36(17) . . ? O2 C49 O1 124.98(16) . . ? O2 C49 C50 117.71(16) . . ? O1 C49 C50 117.30(16) . . ? C56 C50 C51 118.42(16) . . ? C56 C50 C49 120.11(16) . . ? C51 C50 C49 121.47(16) . . ? C52 C51 C50 120.74(17) . . ? C51 C52 C54 120.70(17) . . ? C55 C54 C52 118.46(17) . . ? C55 C54 C57 120.21(17) . . ? C52 C54 C57 121.33(17) . . ? C56 C55 C54 121.09(18) . . ? C55 C56 C50 120.58(18) . . ? O4 C57 O3 126.07(18) . . ? O4 C57 C54 116.32(17) . . ? O3 C57 C54 117.59(17) . . ? O6 C58 O5 125.35(17) . . ? O6 C58 C59 117.64(16) . . ? O5 C58 C59 117.01(16) . . ? C60 C59 C61 118.44(16) . . ? C60 C59 C58 120.93(16) . . ? C61 C59 C58 120.63(16) . . ? C61 C60 C59 121.07(17) 2_546 . ? C60 C61 C59 120.49(17) 2_546 . ? N5 C62 N4 117.21(16) . . ? N5 C62 S1 122.16(15) . . ? N4 C62 S1 120.61(14) . . ? N7 C63 N6 116.49(17) . . ? N7 C63 S2 121.69(15) . . ? N6 C63 S2 121.81(15) . . ? N9 C64 N8 116.57(16) . . ? N9 C64 S3 122.35(14) . . ? N8 C64 S3 121.06(15) . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 26.90 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.754 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.062 #===END data_compound3_h01dmks2 _database_code_CSD 208155 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H44 Br N5 S2' _chemical_formula_weight 474.61 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 16.7880(2) _cell_length_b 17.0600(2) _cell_length_c 18.3130(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5244.90(12) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2032 _exptl_absorpt_coefficient_mu 1.738 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 93507 _diffrn_reflns_av_R_equivalents 0.0790 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5986 _reflns_number_gt 4246 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'Denzo and Scalepack (otwinowski & Minor, 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0618P)^2^+3.4605P] 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 SHELXL _refine_ls_extinction_coef 0.0019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5986 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1113 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.35927(2) 0.146535(19) 0.506763(16) 0.05617(14) Uani 1 1 d . . . S2 S 0.22381(4) 0.13530(4) 0.78500(4) 0.03987(17) Uani 1 1 d . . . S3 S 0.23579(5) 0.11340(4) 0.22480(4) 0.0545(2) Uani 1 1 d . . . N1 N 0.49426(12) 0.31758(14) 0.33142(12) 0.0444(5) Uani 1 1 d . . . N2 N 0.28148(13) 0.20488(12) 0.66648(13) 0.0437(5) Uani 1 1 d . . . H2A H 0.3005 0.2047 0.6217 0.052 Uiso 1 1 calc R . . H2B H 0.2763 0.2494 0.6902 0.052 Uiso 1 1 calc R . . N3 N 0.26989(15) 0.07253(13) 0.65929(12) 0.0473(6) Uani 1 1 d . . . H3A H 0.2891 0.0752 0.6147 0.057 Uiso 1 1 calc R . . H3B H 0.2569 0.0268 0.6781 0.057 Uiso 1 1 calc R . . N4 N 0.26583(15) 0.18538(13) 0.35033(13) 0.0495(6) Uani 1 1 d . . . H4A H 0.2801 0.1863 0.3966 0.059 Uiso 1 1 calc R . . H4B H 0.2531 0.2293 0.3279 0.059 Uiso 1 1 calc R . . N5 N 0.28340(15) 0.05367(13) 0.35123(14) 0.0536(6) Uani 1 1 d . . . H5A H 0.2974 0.0572 0.3974 0.064 Uiso 1 1 calc R . . H5B H 0.2826 0.0077 0.3294 0.064 Uiso 1 1 calc R . . C1 C 0.42273(15) 0.33291(18) 0.38017(16) 0.0484(7) Uani 1 1 d . . . H1A H 0.3760 0.3428 0.3485 0.063 Uiso 1 1 calc R . . H1B H 0.4116 0.2846 0.4083 0.063 Uiso 1 1 calc R . . C2 C 0.43000(17) 0.4000(2) 0.43322(18) 0.0595(8) Uani 1 1 d . . . H1 H 0.4786 0.3935 0.4633 0.077 Uiso 1 1 calc R . . H2 H 0.4345 0.4501 0.4062 0.077 Uiso 1 1 calc R . . C3 C 0.3573(2) 0.4017(3) 0.4819(2) 0.0771(11) Uani 1 1 d . . . H3 H 0.3091 0.4029 0.4508 0.100 Uiso 1 1 calc R . . H4 H 0.3557 0.3527 0.5108 0.100 Uiso 1 1 calc R . . C4 C 0.3549(3) 0.4704(3) 0.5332(3) 0.0987(15) Uani 1 1 d . . . H4C H 0.3066 0.4675 0.5632 0.148 Uiso 1 1 calc R . . H4D H 0.3545 0.5192 0.5051 0.148 Uiso 1 1 calc R . . H4E H 0.4019 0.4693 0.5649 0.148 Uiso 1 1 calc R . . C5 C 0.46925(16) 0.25296(16) 0.27968(16) 0.0465(6) Uani 1 1 d . . . H5 H 0.4222 0.2713 0.2519 0.060 Uiso 1 1 calc R . . H6 H 0.4522 0.2073 0.3091 0.060 Uiso 1 1 calc R . . C6 C 0.53170(19) 0.22549(19) 0.22540(17) 0.0560(8) Uani 1 1 d . . . H6A H 0.5571 0.2715 0.2022 0.073 Uiso 1 1 calc R . . H6B H 0.5735 0.1956 0.2514 0.073 Uiso 1 1 calc R . . C7 C 0.4942(2) 0.17400(19) 0.16699(19) 0.0600(8) Uani 1 1 d . . . H7A H 0.4603 0.1341 0.1909 0.078 Uiso 1 1 calc R . . H7B H 0.4595 0.2067 0.1357 0.078 Uiso 1 1 calc R . . C8 C 0.5546(3) 0.1334(2) 0.1198(2) 0.0813(11) Uani 1 1 d . . . H8A H 0.5271 0.1009 0.0835 0.122 Uiso 1 1 calc R . . H8B H 0.5886 0.1001 0.1503 0.122 Uiso 1 1 calc R . . H8C H 0.5874 0.1726 0.0948 0.122 Uiso 1 1 calc R . . C9 C 0.56726(16) 0.2937(2) 0.37582(16) 0.0534(7) Uani 1 1 d . . . H9A H 0.6107 0.2801 0.3415 0.069 Uiso 1 1 calc R . . H9B H 0.5851 0.3395 0.4046 0.069 Uiso 1 1 calc R . . C10 C 0.5556(2) 0.2263(3) 0.4268(2) 0.0915(15) Uani 1 1 d . . . H10A H 0.5341 0.1811 0.3992 0.119 Uiso 1 1 calc R . . H10B H 0.5158 0.2410 0.4643 0.119 Uiso 1 1 calc R . . C11 C 0.6321(2) 0.2023(3) 0.4641(2) 0.0855(13) Uani 1 1 d . . . H11A H 0.6696 0.1825 0.4267 0.111 Uiso 1 1 calc R . . H11B H 0.6564 0.2492 0.4867 0.111 Uiso 1 1 calc R . . C12 C 0.6216(3) 0.1413(4) 0.5210(3) 0.141(3) Uani 1 1 d . . . H12A H 0.6735 0.1287 0.5427 0.212 Uiso 1 1 calc R . . H12B H 0.5989 0.0940 0.4989 0.212 Uiso 1 1 calc R . . H12C H 0.5857 0.1608 0.5590 0.212 Uiso 1 1 calc R . . C13 C 0.51873(18) 0.39099(17) 0.28984(16) 0.0508(7) Uani 1 1 d . B . H13A H 0.5333 0.4317 0.3259 0.066 Uiso 1 1 calc R . . H13B H 0.5673 0.3786 0.2614 0.066 Uiso 1 1 calc R . . C14 C 0.4581(3) 0.4254(2) 0.2385(2) 0.0744(11) Uani 1 1 d . . . H14A H 0.4468 0.3850 0.2011 0.097 Uiso 1 1 calc R A 1 H14B H 0.4084 0.4325 0.2669 0.097 Uiso 1 1 calc R A 1 C15A C 0.5155(5) 0.4819(4) 0.1908(5) 0.0540(17) Uani 0.50 1 d P B 2 H15A H 0.4986 0.5363 0.2017 0.065 Uiso 0.50 1 calc PR B 2 H15B H 0.5696 0.4759 0.2115 0.065 Uiso 0.50 1 calc PR B 2 C17 C 0.26051(15) 0.13760(14) 0.69835(15) 0.0373(5) Uani 1 1 d . . . C18 C 0.26349(16) 0.11778(15) 0.31437(16) 0.0430(6) Uani 1 1 d . . . C16A C 0.5220(5) 0.4789(4) 0.1348(5) 0.0652(18) Uani 0.50 1 d P B 2 H16A H 0.5598 0.5191 0.1187 0.098 Uiso 0.50 1 calc PR B 2 H16B H 0.4703 0.4878 0.1114 0.098 Uiso 0.50 1 calc PR B 2 H16C H 0.5420 0.4269 0.1213 0.098 Uiso 0.50 1 calc PR B 2 C16 C 0.4667(4) 0.5230(4) 0.1319(4) 0.0606(17) Uani 0.50 1 d P B 1 H16D H 0.4835 0.5779 0.1276 0.091 Uiso 0.50 1 calc PR B 1 H16E H 0.4113 0.5180 0.1159 0.091 Uiso 0.50 1 calc PR B 1 H16F H 0.5008 0.4901 0.1011 0.091 Uiso 0.50 1 calc PR B 1 C15 C 0.4727(6) 0.5011(4) 0.1983(5) 0.064(2) Uani 0.50 1 d P B 1 H15C H 0.4396 0.5395 0.2250 0.077 Uiso 0.50 1 calc PR B 1 H15D H 0.5284 0.5143 0.2110 0.077 Uiso 0.50 1 calc PR B 1 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 0.0703(2) 0.0549(2) 0.04333(19) 0.00697(12) 0.00433(14) 0.00260(14) S2 0.0434(4) 0.0321(3) 0.0440(4) -0.0005(3) -0.0025(3) -0.0015(3) S3 0.0770(5) 0.0314(3) 0.0549(4) -0.0012(3) -0.0128(4) -0.0041(3) N1 0.0312(11) 0.0572(14) 0.0448(12) 0.0047(10) 0.0007(9) -0.0041(10) N2 0.0512(13) 0.0327(11) 0.0474(13) 0.0007(9) 0.0016(10) -0.0024(9) N3 0.0678(16) 0.0325(11) 0.0416(12) -0.0023(9) 0.0001(11) -0.0089(10) N4 0.0678(16) 0.0304(11) 0.0502(13) -0.0001(10) -0.0083(12) 0.0019(10) N5 0.0744(17) 0.0324(11) 0.0540(14) 0.0006(10) -0.0053(13) 0.0044(11) C1 0.0301(14) 0.0667(18) 0.0484(16) 0.0082(14) 0.0024(12) 0.0004(12) C2 0.0402(16) 0.081(2) 0.0569(19) -0.0012(16) 0.0035(14) 0.0035(15) C3 0.060(2) 0.092(3) 0.080(3) 0.000(2) 0.0263(18) 0.0116(19) C4 0.087(3) 0.118(4) 0.091(3) -0.011(3) 0.031(3) 0.029(3) C5 0.0368(14) 0.0477(15) 0.0551(16) 0.0050(12) -0.0038(12) -0.0080(12) C6 0.0503(18) 0.0555(17) 0.0623(19) -0.0073(14) 0.0009(15) -0.0073(14) C7 0.060(2) 0.0511(17) 0.069(2) -0.0046(15) -0.0104(16) -0.0052(14) C8 0.090(3) 0.080(3) 0.074(3) -0.027(2) -0.007(2) -0.006(2) C9 0.0310(14) 0.082(2) 0.0474(16) -0.0011(15) -0.0017(12) 0.0024(14) C10 0.0396(18) 0.145(4) 0.090(3) 0.057(3) -0.0071(18) 0.013(2) C11 0.048(2) 0.142(4) 0.067(2) 0.010(3) -0.0094(17) 0.033(2) C12 0.080(3) 0.229(8) 0.115(4) 0.084(5) -0.010(3) 0.049(4) C13 0.0505(16) 0.0539(17) 0.0480(16) -0.0026(13) 0.0051(13) -0.0170(13) C14 0.100(3) 0.0558(19) 0.067(2) 0.0171(17) -0.020(2) -0.0271(19) C15A 0.058(5) 0.043(4) 0.061(5) 0.002(3) 0.002(4) -0.011(3) C17 0.0344(13) 0.0340(12) 0.0435(14) -0.0013(11) -0.0087(11) -0.0029(10) C18 0.0440(15) 0.0310(12) 0.0540(16) -0.0002(11) 0.0000(12) -0.0026(11) C16A 0.067(5) 0.067(4) 0.062(5) 0.011(4) 0.004(4) -0.008(3) C16 0.070(4) 0.038(3) 0.074(5) 0.012(3) 0.007(4) 0.010(3) C15 0.075(6) 0.040(4) 0.078(6) 0.005(3) 0.009(5) -0.003(4) _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 S2 C17 1.703(3) . ? S3 C18 1.707(3) . ? N1 C5 1.513(4) . ? N1 C1 1.519(3) . ? N1 C13 1.522(4) . ? N1 C9 1.526(3) . ? N2 C17 1.335(3) . ? N3 C17 1.330(3) . ? N4 C18 1.329(4) . ? N5 C18 1.328(3) . ? C1 C2 1.507(4) . ? C2 C3 1.511(4) . ? C3 C4 1.503(6) . ? C5 C6 1.519(4) . ? C6 C7 1.521(4) . ? C7 C8 1.501(5) . ? C9 C10 1.493(5) . ? C10 C11 1.511(4) . ? C11 C12 1.484(7) . ? C13 C14 1.505(5) . ? C14 C15 1.507(8) . ? C14 C15A 1.619(8) . ? C15A C16A 1.032(10) . ? C16 C15 1.276(11) . ? 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 C5 N1 C1 105.9(2) . . ? C5 N1 C13 111.2(2) . . ? C1 N1 C13 111.4(2) . . ? C5 N1 C9 111.2(2) . . ? C1 N1 C9 111.6(2) . . ? C13 N1 C9 105.7(2) . . ? C2 C1 N1 116.5(2) . . ? C3 C2 C1 109.2(3) . . ? C4 C3 C2 113.9(4) . . ? N1 C5 C6 116.3(2) . . ? C7 C6 C5 110.7(3) . . ? C8 C7 C6 113.1(3) . . ? C10 C9 N1 115.7(2) . . ? C9 C10 C11 112.3(3) . . ? C12 C11 C10 114.0(4) . . ? C14 C13 N1 116.8(2) . . ? C15 C14 C13 121.9(5) . . ? C15 C14 C15A 29.4(3) . . ? C13 C14 C15A 99.6(4) . . ? C16A C15A C14 124.7(7) . . ? N3 C17 N2 116.8(3) . . ? N3 C17 S2 121.7(2) . . ? N2 C17 S2 121.5(2) . . ? N4 C18 N5 117.1(3) . . ? N4 C18 S3 121.5(2) . . ? N5 C18 S3 121.4(2) . . ? C16 C15 C14 134.8(7) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.433 _refine_diff_density_min -0.853 _refine_diff_density_rms 0.062