# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_dip _database_code_depnum_ccdc_archive 'CCDC 894067' #TrackingRef '3d ani-HugerSchoff.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H28 N4 S' _chemical_formula_weight 428.58 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5021(13) _cell_length_b 11.2799(14) _cell_length_c 24.739(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.125(8) _cell_angle_gamma 90.00 _cell_volume 2641.0(6) _cell_formula_units_Z 5 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1140 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29006 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 26.56 _reflns_number_total 4573 _reflns_number_gt 2737 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0676P)^2^+0.1619P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4573 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1134 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1242 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.32498(8) 0.42793(6) 0.44929(3) 0.0668(3) Uani 1 1 d . . . N2 N 0.07296(19) 0.68022(17) 0.45074(7) 0.0474(5) Uani 1 1 d . . . N1 N 0.4734(2) 0.54306(16) 0.37928(7) 0.0504(5) Uani 1 1 d . . . C5 C -0.0785(3) 0.6881(2) 0.45506(10) 0.0592(7) Uani 1 1 d . . . H5A H -0.1085 0.6227 0.4768 0.071 Uiso 1 1 calc R . . H5B H -0.1285 0.6823 0.4192 0.071 Uiso 1 1 calc R . . C1 C 0.1568(3) 0.6918(2) 0.50320(9) 0.0570(7) Uani 1 1 d . . . H1A H 0.2565 0.6852 0.4981 0.068 Uiso 1 1 calc R . . H1B H 0.1326 0.6285 0.5272 0.068 Uiso 1 1 calc R . . C3 C -0.0294(3) 0.8244(3) 0.53471(11) 0.0731(8) Uani 1 1 d . . . H3A H -0.0578 0.7678 0.5612 0.088 Uiso 1 1 calc R . . H3B H -0.0478 0.9035 0.5477 0.088 Uiso 1 1 calc R . . C2 C 0.1280(3) 0.8106(2) 0.52852(10) 0.0687(8) Uani 1 1 d . . . H2A H 0.1591 0.8738 0.5058 0.082 Uiso 1 1 calc R . . H2B H 0.1808 0.8165 0.5638 0.082 Uiso 1 1 calc R . . C4 C -0.1146(3) 0.8038(3) 0.48089(11) 0.0716(8) Uani 1 1 d . . . H4A H -0.2144 0.8043 0.4865 0.086 Uiso 1 1 calc R . . H4B H -0.0973 0.8683 0.4564 0.086 Uiso 1 1 calc R . . C6 C 0.4868(3) 0.6171(2) 0.33136(10) 0.0612(7) Uani 1 1 d . . . H6A H 0.5570 0.6781 0.3401 0.073 Uiso 1 1 calc R . . H6B H 0.3972 0.6557 0.3210 0.073 Uiso 1 1 calc R . . C10 C 0.6002(3) 0.4724(2) 0.39524(10) 0.0662(8) Uani 1 1 d . . . H10A H 0.5819 0.4214 0.4254 0.079 Uiso 1 1 calc R . . H10B H 0.6774 0.5250 0.4073 0.079 Uiso 1 1 calc R . . C7 C 0.5293(3) 0.5440(3) 0.28478(11) 0.0798(9) Uani 1 1 d . . . H7A H 0.5450 0.5960 0.2547 0.096 Uiso 1 1 calc R . . H7B H 0.4528 0.4905 0.2729 0.096 Uiso 1 1 calc R . . C8 C 0.6628(3) 0.4719(3) 0.29966(12) 0.0887(10) Uani 1 1 d . . . H8A H 0.6817 0.4209 0.2696 0.106 Uiso 1 1 calc R . . H8B H 0.7427 0.5247 0.3071 0.106 Uiso 1 1 calc R . . C9 C 0.6428(3) 0.3977(3) 0.34929(11) 0.0817(9) Uani 1 1 d . . . H9A H 0.5707 0.3384 0.3402 0.098 Uiso 1 1 calc R . . H9B H 0.7303 0.3568 0.3606 0.098 Uiso 1 1 calc R . . C11 C 0.3595(3) 0.53842(19) 0.40773(9) 0.0446(6) Uani 1 1 d . . . N3 N 0.2685(2) 0.63591(15) 0.40168(7) 0.0444(5) Uani 1 1 d . . . C17 C 0.2477(3) 0.8430(2) 0.37389(9) 0.0501(6) Uani 1 1 d . . . H17 H 0.1647 0.8230 0.3531 0.060 Uiso 1 1 calc R . . C16 C 0.2945(3) 0.9604(2) 0.37441(10) 0.0540(7) Uani 1 1 d . . . C12 C 0.3219(3) 0.7558(2) 0.40362(9) 0.0466(6) Uani 1 1 d . . . C13 C 0.4441(3) 0.7857(2) 0.43493(10) 0.0599(7) Uani 1 1 d . . . H13 H 0.4948 0.7283 0.4554 0.072 Uiso 1 1 calc R . . C15 C 0.4188(3) 0.9899(2) 0.40593(12) 0.0641(8) Uani 1 1 d . . . C14 C 0.4902(3) 0.9014(2) 0.43552(12) 0.0712(8) Uani 1 1 d . . . H14 H 0.5728 0.9208 0.4567 0.085 Uiso 1 1 calc R . . C19 C 0.2121(3) 1.0515(2) 0.34078(11) 0.0760(9) Uani 1 1 d . . . H19A H 0.1315 1.0147 0.3215 0.114 Uiso 1 1 calc R . . H19B H 0.2709 1.0857 0.3153 0.114 Uiso 1 1 calc R . . H19C H 0.1810 1.1126 0.3640 0.114 Uiso 1 1 calc R . . C18 C 0.4738(3) 1.1163(2) 0.40777(14) 0.0964(11) Uani 1 1 d . . . H18A H 0.5577 1.1208 0.4324 0.145 Uiso 1 1 calc R . . H18B H 0.4031 1.1682 0.4199 0.145 Uiso 1 1 calc R . . H18C H 0.4955 1.1398 0.3721 0.145 Uiso 1 1 calc R . . C20 C 0.1204(3) 0.6190(2) 0.40867(9) 0.0453(6) Uani 1 1 d . . . C22 C 0.1502(3) 0.5369(2) 0.23581(9) 0.0579(7) Uani 1 1 d . . . C21 C 0.1140(2) 0.5835(2) 0.28504(9) 0.0535(7) Uani 1 1 d . . . H21 H 0.1113 0.6654 0.2894 0.064 Uiso 1 1 calc R . . C28 C 0.0821(2) 0.5117(2) 0.32734(9) 0.0505(6) Uani 1 1 d . . . C26 C 0.1193(3) 0.3440(2) 0.27145(11) 0.0737(8) Uani 1 1 d . . . H26 H 0.1199 0.2621 0.2671 0.088 Uiso 1 1 calc R . . C27 C 0.0845(3) 0.3905(2) 0.31968(10) 0.0670(8) Uani 1 1 d . . . H27 H 0.0624 0.3401 0.3474 0.080 Uiso 1 1 calc R . . C25 C 0.1537(3) 0.4152(3) 0.22895(10) 0.0613(7) Uani 1 1 d . . . C23 C 0.1876(3) 0.6220(3) 0.19188(11) 0.0892(10) Uani 1 1 d . . . H23A H 0.1740 0.7020 0.2036 0.134 Uiso 1 1 calc R . . H23B H 0.1280 0.6070 0.1592 0.134 Uiso 1 1 calc R . . H23C H 0.2847 0.6109 0.1851 0.134 Uiso 1 1 calc R . . C24 C 0.1917(4) 0.3601(3) 0.17620(12) 0.1008(11) Uani 1 1 d . . . H24A H 0.1795 0.2757 0.1777 0.151 Uiso 1 1 calc R . . H24B H 0.2884 0.3780 0.1710 0.151 Uiso 1 1 calc R . . H24C H 0.1313 0.3918 0.1465 0.151 Uiso 1 1 calc R . . N4 N 0.0372(2) 0.55775(17) 0.37647(8) 0.0531(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0808(6) 0.0532(4) 0.0687(5) 0.0155(3) 0.0201(4) 0.0048(4) N2 0.0381(13) 0.0616(13) 0.0429(11) -0.0047(10) 0.0061(9) 0.0011(10) N1 0.0522(14) 0.0460(12) 0.0540(12) 0.0067(10) 0.0097(11) 0.0075(10) C5 0.0526(18) 0.0696(19) 0.0566(16) -0.0004(14) 0.0116(13) -0.0046(14) C1 0.0577(17) 0.0677(18) 0.0453(14) -0.0003(13) 0.0026(12) 0.0077(14) C3 0.085(2) 0.074(2) 0.0618(18) -0.0106(14) 0.0148(16) 0.0129(16) C2 0.078(2) 0.072(2) 0.0557(16) -0.0146(14) 0.0019(14) -0.0011(16) C4 0.0613(19) 0.083(2) 0.0719(19) -0.0009(16) 0.0151(15) 0.0149(16) C6 0.0583(18) 0.0571(16) 0.0707(18) 0.0147(14) 0.0196(14) 0.0060(14) C10 0.0586(19) 0.0692(18) 0.0710(18) 0.0044(15) 0.0077(14) 0.0188(15) C7 0.083(2) 0.096(2) 0.0650(18) 0.0135(16) 0.0284(16) 0.0171(18) C8 0.086(2) 0.103(2) 0.082(2) 0.0092(19) 0.0341(18) 0.035(2) C9 0.088(2) 0.077(2) 0.082(2) 0.0055(17) 0.0184(17) 0.0309(17) C11 0.0502(16) 0.0404(14) 0.0434(13) -0.0013(11) 0.0046(12) 0.0002(12) N3 0.0443(13) 0.0403(12) 0.0493(11) 0.0003(9) 0.0079(9) -0.0018(10) C17 0.0500(16) 0.0491(16) 0.0519(14) -0.0009(12) 0.0088(12) 0.0005(13) C16 0.0613(19) 0.0434(16) 0.0591(16) 0.0008(13) 0.0161(14) 0.0067(14) C12 0.0482(16) 0.0382(14) 0.0542(15) -0.0018(12) 0.0089(12) -0.0008(12) C13 0.0524(18) 0.0473(17) 0.0776(18) -0.0035(14) -0.0075(15) 0.0015(14) C15 0.065(2) 0.0416(16) 0.088(2) -0.0073(15) 0.0171(17) -0.0041(15) C14 0.0538(18) 0.0496(18) 0.108(2) -0.0113(16) -0.0060(16) -0.0017(15) C19 0.096(2) 0.0580(18) 0.0765(19) 0.0089(15) 0.0197(17) 0.0149(16) C18 0.096(3) 0.0542(19) 0.140(3) -0.0096(19) 0.019(2) -0.0181(17) C20 0.0452(17) 0.0447(14) 0.0467(14) 0.0026(12) 0.0077(12) 0.0001(12) C22 0.0580(18) 0.069(2) 0.0466(15) 0.0036(14) 0.0038(13) 0.0021(14) C21 0.0590(18) 0.0487(15) 0.0532(15) -0.0038(13) 0.0069(13) -0.0022(13) C28 0.0495(16) 0.0520(16) 0.0494(15) -0.0046(13) 0.0011(12) -0.0071(13) C26 0.104(2) 0.0527(17) 0.0622(18) -0.0074(15) -0.0050(17) 0.0036(16) C27 0.094(2) 0.0543(18) 0.0517(16) 0.0007(14) 0.0040(15) -0.0081(15) C25 0.0680(19) 0.0651(19) 0.0497(16) -0.0100(14) -0.0003(13) 0.0097(15) C23 0.109(3) 0.096(2) 0.0650(19) 0.0092(17) 0.0217(17) -0.010(2) C24 0.128(3) 0.111(3) 0.0655(19) -0.0226(18) 0.0165(19) 0.029(2) N4 0.0520(13) 0.0600(14) 0.0482(12) -0.0075(10) 0.0091(10) -0.0095(11) _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 C11 1.667(2) . ? N2 C20 1.359(3) . ? N2 C5 1.456(3) . ? N2 C1 1.467(3) . ? N1 C11 1.344(3) . ? N1 C6 1.465(3) . ? N1 C10 1.469(3) . ? C5 C4 1.506(3) . ? C1 C2 1.514(3) . ? C3 C4 1.513(4) . ? C3 C2 1.525(3) . ? C6 C7 1.501(3) . ? C10 C9 1.499(3) . ? C7 C8 1.523(4) . ? C8 C9 1.512(4) . ? C11 N3 1.399(3) . ? N3 C12 1.443(3) . ? N3 C20 1.445(3) . ? C17 C12 1.383(3) . ? C17 C16 1.397(3) . ? C16 C15 1.396(3) . ? C16 C19 1.499(3) . ? C12 C13 1.379(3) . ? C13 C14 1.377(3) . ? C15 C14 1.380(4) . ? C15 C18 1.517(4) . ? C20 N4 1.275(3) . ? C22 C25 1.384(3) . ? C22 C21 1.398(3) . ? C22 C23 1.516(3) . ? C21 C28 1.379(3) . ? C28 C27 1.380(3) . ? C28 N4 1.422(3) . ? C26 C27 1.371(3) . ? C26 C25 1.385(4) . ? C25 C24 1.518(3) . ? 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 C20 N2 C5 119.05(19) . . ? C20 N2 C1 122.12(19) . . ? C5 N2 C1 113.08(18) . . ? C11 N1 C6 125.34(19) . . ? C11 N1 C10 121.17(19) . . ? C6 N1 C10 113.48(19) . . ? N2 C5 C4 110.4(2) . . ? N2 C1 C2 109.9(2) . . ? C4 C3 C2 110.4(2) . . ? C1 C2 C3 110.3(2) . . ? C5 C4 C3 112.5(2) . . ? N1 C6 C7 110.9(2) . . ? N1 C10 C9 111.8(2) . . ? C6 C7 C8 112.5(2) . . ? C9 C8 C7 109.2(2) . . ? C10 C9 C8 111.5(2) . . ? N1 C11 N3 115.64(19) . . ? N1 C11 S1 124.37(18) . . ? N3 C11 S1 119.98(17) . . ? C11 N3 C12 121.37(19) . . ? C11 N3 C20 118.88(18) . . ? C12 N3 C20 117.55(18) . . ? C12 C17 C16 121.5(2) . . ? C15 C16 C17 119.0(2) . . ? C15 C16 C19 121.4(2) . . ? C17 C16 C19 119.7(3) . . ? C13 C12 C17 119.3(2) . . ? C13 C12 N3 121.6(2) . . ? C17 C12 N3 119.2(2) . . ? C14 C13 C12 119.3(2) . . ? C14 C15 C16 118.4(2) . . ? C14 C15 C18 120.8(3) . . ? C16 C15 C18 120.9(3) . . ? C13 C14 C15 122.6(3) . . ? N4 C20 N2 121.6(2) . . ? N4 C20 N3 123.6(2) . . ? N2 C20 N3 114.7(2) . . ? C25 C22 C21 119.4(2) . . ? C25 C22 C23 122.0(2) . . ? C21 C22 C23 118.5(2) . . ? C28 C21 C22 121.9(2) . . ? C21 C28 C27 118.1(2) . . ? C21 C28 N4 122.5(2) . . ? C27 C28 N4 119.3(2) . . ? C27 C26 C25 122.0(3) . . ? C26 C27 C28 120.5(2) . . ? C22 C25 C26 118.2(2) . . ? C22 C25 C24 121.4(3) . . ? C26 C25 C24 120.4(3) . . ? C20 N4 C28 121.0(2) . . ? _diffrn_measured_fraction_theta_max 0.831 _diffrn_reflns_theta_full 26.56 _diffrn_measured_fraction_theta_full 0.831 _refine_diff_density_max 0.153 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.037 data_nk_13l _database_code_depnum_ccdc_archive 'CCDC 894068' #TrackingRef 'NK_13L Final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 Br2 N2 O2 S2' _chemical_formula_weight 427.16 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' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1289(3) _cell_length_b 11.2225(3) _cell_length_c 11.7532(4) _cell_angle_alpha 94.059(2) _cell_angle_beta 112.599(2) _cell_angle_gamma 107.266(2) _cell_volume 1151.66(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 836 _exptl_absorpt_coefficient_mu 7.399 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18708 _diffrn_reflns_av_R_equivalents 0.0928 _diffrn_reflns_av_sigmaI/netI 0.0793 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6342 _reflns_number_gt 3592 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00340(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6342 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.383 _refine_ls_restrained_S_all 1.383 _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 0.97552(5) 1.44568(3) 1.15678(3) 0.05776(14) Uani 1 1 d . . . Br2 Br 0.41805(5) 1.40699(3) 1.17829(3) 0.05989(14) Uani 1 1 d . . . S1 S 0.92780(9) 1.02001(8) 0.83646(8) 0.0424(2) Uani 1 1 d . . . S2 S 0.30520(10) 0.94267(7) 0.87616(7) 0.0410(2) Uani 1 1 d . . . C5 C 0.8653(4) 1.1316(3) 0.8878(3) 0.0341(7) Uani 1 1 d . . . C1 C 0.8705(4) 1.3109(3) 1.0135(3) 0.0351(8) Uani 1 1 d . . . C4 C 0.7123(3) 1.1085(3) 0.8067(3) 0.0294(7) Uani 1 1 d . . . C6 C 0.9470(4) 1.2340(3) 0.9917(3) 0.0392(8) Uani 1 1 d . . . H6 H 1.0490 1.2500 1.0443 0.047 Uiso 1 1 calc R . . C7 C 0.2709(4) 1.2651(3) 0.7984(3) 0.0399(8) Uani 1 1 d . . . H7 H 0.2435 1.2960 0.7246 0.048 Uiso 1 1 calc R . . C2 C 0.7197(4) 1.2893(3) 0.9345(3) 0.0400(8) Uani 1 1 d . . . H2 H 0.6714 1.3427 0.9506 0.048 Uiso 1 1 calc R . . C3 C 0.6411(4) 1.1887(3) 0.8320(3) 0.0388(8) Uani 1 1 d . . . H3 H 0.5396 1.1743 0.7793 0.047 Uiso 1 1 calc R . . C9 C 0.5266(4) 0.6658(3) 0.4589(3) 0.0522(10) Uani 1 1 d . . . H9A H 0.4912 0.6214 0.5154 0.063 Uiso 1 1 calc R . . H9B H 0.4413 0.6412 0.3763 0.063 Uiso 1 1 calc R . . C11 C 0.8348(4) 0.8008(3) 0.6259(3) 0.0502(9) Uani 1 1 d . . . H11A H 0.9141 0.8189 0.7109 0.060 Uiso 1 1 calc R . . H11B H 0.8802 0.8449 0.5746 0.060 Uiso 1 1 calc R . . C8 C 0.5788(4) 0.8076(3) 0.5060(3) 0.0461(9) Uani 1 1 d . . . H8A H 0.6041 0.8527 0.4455 0.055 Uiso 1 1 calc R . . H8B H 0.4976 0.8293 0.5162 0.055 Uiso 1 1 calc R . . C10 C 0.7678(4) 0.6588(3) 0.5726(3) 0.0534(10) Uani 1 1 d . . . H10A H 0.8467 0.6296 0.5671 0.064 Uiso 1 1 calc R . . H10B H 0.7317 0.6148 0.6289 0.064 Uiso 1 1 calc R . . O1 O 0.6446(3) 0.6279(2) 0.4508(2) 0.0537(7) Uani 1 1 d . . . N1 N 0.7136(3) 0.8453(2) 0.6273(2) 0.0382(7) Uani 1 1 d . . . N2 N 0.6449(3) 1.0042(2) 0.7075(2) 0.0350(6) Uani 1 1 d . . . C15 C 0.3128(3) 1.0987(3) 0.9069(3) 0.0320(7) Uani 1 1 d . . . C13 C 0.3546(3) 1.2964(3) 1.0230(3) 0.0369(8) Uani 1 1 d . . . C16 C 0.2673(3) 1.1422(3) 0.7942(3) 0.0304(7) Uani 1 1 d . . . C12 C 0.3548(3) 1.1742(3) 1.0222(3) 0.0356(7) Uani 1 1 d . . . H12 H 0.3820 1.1433 1.0961 0.043 Uiso 1 1 calc R . . C14 C 0.3152(4) 1.3431(3) 0.9121(3) 0.0434(8) Uani 1 1 d . . . H14 H 0.3189 1.4272 0.9151 0.052 Uiso 1 1 calc R . . O2 O 0.1856(3) 0.6428(2) 0.4553(2) 0.0592(7) Uani 1 1 d . . . N3 N 0.2052(3) 0.8408(2) 0.6304(2) 0.0386(7) Uani 1 1 d . . . C19 C 0.1996(4) 0.6251(3) 0.5772(3) 0.0526(10) Uani 1 1 d . . . H19A H 0.2546 0.5671 0.6034 0.063 Uiso 1 1 calc R . . H19B H 0.0987 0.5869 0.5743 0.063 Uiso 1 1 calc R . . C20 C 0.2833(4) 0.7504(3) 0.6723(3) 0.0440(9) Uani 1 1 d . . . H20A H 0.2866 0.7364 0.7537 0.053 Uiso 1 1 calc R . . H20B H 0.3875 0.7852 0.6813 0.053 Uiso 1 1 calc R . . C17 C 0.1787(4) 0.8554(3) 0.5008(3) 0.0473(9) Uani 1 1 d . . . H17A H 0.2751 0.8996 0.4979 0.057 Uiso 1 1 calc R . . H17B H 0.1134 0.9055 0.4731 0.057 Uiso 1 1 calc R . . C18 C 0.1033(4) 0.7243(3) 0.4145(3) 0.0587(11) Uani 1 1 d . . . H18A H 0.0015 0.6857 0.4097 0.070 Uiso 1 1 calc R . . H18B H 0.0931 0.7337 0.3304 0.070 Uiso 1 1 calc R . . C22 C 0.2405(3) 0.9478(3) 0.7153(3) 0.0319(7) Uani 1 1 d . . . N4 N 0.2256(3) 1.0535(2) 0.6851(2) 0.0354(6) Uani 1 1 d . . . C23 C 0.7434(3) 0.9504(3) 0.7110(3) 0.0325(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0688(3) 0.0435(2) 0.0489(2) -0.00462(17) 0.0197(2) 0.0137(2) Br2 0.0848(3) 0.0556(2) 0.0449(2) 0.00251(18) 0.0314(2) 0.0290(2) S1 0.0294(5) 0.0487(5) 0.0421(5) -0.0036(4) 0.0092(4) 0.0152(4) S2 0.0521(6) 0.0318(4) 0.0333(5) 0.0104(3) 0.0133(4) 0.0125(4) C5 0.0339(19) 0.0347(17) 0.0344(18) 0.0079(14) 0.0159(15) 0.0112(15) C1 0.042(2) 0.0290(16) 0.0332(19) 0.0112(14) 0.0166(17) 0.0096(15) C4 0.0250(18) 0.0344(17) 0.0254(17) 0.0085(13) 0.0075(14) 0.0098(14) C6 0.0328(19) 0.0372(17) 0.0380(19) 0.0062(15) 0.0107(16) 0.0057(15) C7 0.046(2) 0.0458(19) 0.0343(19) 0.0147(15) 0.0156(16) 0.0250(17) C2 0.050(2) 0.0369(18) 0.042(2) 0.0112(16) 0.0221(18) 0.0238(17) C3 0.036(2) 0.0423(18) 0.0390(19) 0.0128(15) 0.0132(16) 0.0181(16) C9 0.053(2) 0.039(2) 0.045(2) 0.0017(16) 0.0099(19) 0.0067(18) C11 0.044(2) 0.054(2) 0.050(2) -0.0018(17) 0.0185(18) 0.0196(18) C8 0.042(2) 0.045(2) 0.035(2) 0.0016(15) 0.0057(17) 0.0089(17) C10 0.057(2) 0.054(2) 0.051(2) -0.0007(18) 0.024(2) 0.024(2) O1 0.0657(18) 0.0534(14) 0.0396(14) -0.0032(11) 0.0232(14) 0.0198(14) N1 0.0339(16) 0.0400(15) 0.0347(16) -0.0021(12) 0.0106(13) 0.0126(13) N2 0.0342(16) 0.0370(14) 0.0322(15) 0.0050(12) 0.0114(12) 0.0144(13) C15 0.0252(17) 0.0354(17) 0.0340(18) 0.0111(14) 0.0128(14) 0.0077(14) C13 0.037(2) 0.0391(18) 0.038(2) 0.0070(15) 0.0177(16) 0.0159(15) C16 0.0261(18) 0.0312(17) 0.0332(18) 0.0075(14) 0.0124(14) 0.0092(14) C12 0.039(2) 0.0351(17) 0.0313(18) 0.0087(14) 0.0160(15) 0.0097(15) C14 0.047(2) 0.0414(19) 0.049(2) 0.0130(17) 0.0213(18) 0.0237(17) O2 0.0705(18) 0.0556(15) 0.0470(16) -0.0015(12) 0.0176(14) 0.0288(14) N3 0.0436(17) 0.0340(14) 0.0300(15) 0.0056(12) 0.0107(13) 0.0093(13) C19 0.053(2) 0.0341(18) 0.054(2) -0.0006(17) 0.010(2) 0.0122(18) C20 0.048(2) 0.0367(17) 0.0391(19) 0.0069(15) 0.0097(17) 0.0150(17) C17 0.057(2) 0.0427(19) 0.0356(19) 0.0081(15) 0.0149(18) 0.0149(18) C18 0.067(3) 0.058(2) 0.035(2) -0.0026(18) 0.0050(19) 0.026(2) C22 0.0232(17) 0.0284(17) 0.0361(17) 0.0044(14) 0.0100(14) 0.0024(13) N4 0.0360(16) 0.0336(14) 0.0303(15) 0.0059(12) 0.0089(12) 0.0110(12) C23 0.0302(18) 0.0313(17) 0.0304(17) 0.0075(13) 0.0105(14) 0.0060(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.888(3) . ? Br2 C13 1.894(3) . ? S1 C5 1.729(3) . ? S1 C23 1.769(3) . ? S2 C15 1.735(3) . ? S2 C22 1.759(3) . ? C5 C6 1.399(4) . ? C5 C4 1.403(4) . ? C1 C6 1.388(4) . ? C1 C2 1.383(4) . ? C4 N2 1.384(3) . ? C4 C3 1.390(4) . ? C7 C16 1.366(4) . ? C7 C14 1.376(4) . ? C2 C3 1.377(4) . ? C9 O1 1.414(4) . ? C9 C8 1.507(4) . ? C11 N1 1.461(4) . ? C11 C10 1.511(4) . ? C8 N1 1.467(4) . ? C10 O1 1.423(3) . ? N1 C23 1.358(3) . ? N2 C23 1.300(3) . ? C15 C12 1.384(4) . ? C15 C16 1.401(4) . ? C13 C12 1.372(4) . ? C13 C14 1.398(4) . ? C16 N4 1.402(3) . ? O2 C19 1.419(4) . ? O2 C18 1.403(4) . ? N3 C22 1.366(3) . ? N3 C20 1.465(4) . ? N3 C17 1.472(4) . ? C19 C20 1.511(4) . ? C17 C18 1.517(4) . ? C22 N4 1.297(3) . ? 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 S1 C23 88.12(14) . . ? C15 S2 C22 88.38(14) . . ? C6 C5 C4 121.4(3) . . ? C6 C5 S1 128.6(2) . . ? C4 C5 S1 110.1(2) . . ? C6 C1 C2 121.6(3) . . ? C6 C1 Br1 118.6(2) . . ? C2 C1 Br1 119.7(2) . . ? N2 C4 C3 125.7(3) . . ? N2 C4 C5 115.5(3) . . ? C3 C4 C5 118.8(3) . . ? C1 C6 C5 117.7(3) . . ? C16 C7 C14 119.9(3) . . ? C3 C2 C1 120.0(3) . . ? C2 C3 C4 120.5(3) . . ? O1 C9 C8 112.1(3) . . ? N1 C11 C10 109.0(3) . . ? N1 C8 C9 108.9(3) . . ? O1 C10 C11 111.4(3) . . ? C10 O1 C9 109.6(2) . . ? C23 N1 C11 121.8(3) . . ? C23 N1 C8 119.1(3) . . ? C11 N1 C8 114.1(2) . . ? C23 N2 C4 109.9(3) . . ? C12 C15 C16 122.2(3) . . ? C12 C15 S2 127.9(2) . . ? C16 C15 S2 109.8(2) . . ? C12 C13 C14 121.3(3) . . ? C12 C13 Br2 119.5(2) . . ? C14 C13 Br2 119.1(2) . . ? C7 C16 N4 125.5(3) . . ? C7 C16 C15 119.1(3) . . ? N4 C16 C15 115.4(2) . . ? C13 C12 C15 117.2(3) . . ? C7 C14 C13 120.2(3) . . ? C19 O2 C18 110.3(2) . . ? C22 N3 C20 118.7(2) . . ? C22 N3 C17 116.9(3) . . ? C20 N3 C17 113.2(2) . . ? O2 C19 C20 111.3(3) . . ? N3 C20 C19 109.8(3) . . ? N3 C17 C18 109.1(3) . . ? O2 C18 C17 112.9(3) . . ? N4 C22 N3 124.3(3) . . ? N4 C22 S2 116.9(2) . . ? N3 C22 S2 118.8(2) . . ? C22 N4 C16 109.5(2) . . ? N2 C23 N1 124.8(3) . . ? N2 C23 S1 116.4(2) . . ? N1 C23 S1 118.8(2) . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.573 _refine_diff_density_min -0.739 _refine_diff_density_rms 0.094