Supplementary Material for PCCP This journal is © The Owner Societies 2010 data_qub4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H17 F6 N3 O4 S2' _chemical_formula_weight 541.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.8070(11) _cell_length_b 15.6746(16) _cell_length_c 13.6445(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.318(2) _cell_angle_gamma 90.00 _cell_volume 2311.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description tablet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9402 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker Platinum 200 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28617 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 31.10 _reflns_number_total 5724 _reflns_number_gt 4662 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT v7.34a' _computing_data_reduction 'Bruker SAINT v7.34a' _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^)+(0.1519P)^2^+1.7697P] 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 contr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5724 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0906 _refine_ls_R_factor_gt 0.0725 _refine_ls_wR_factor_ref 0.2368 _refine_ls_wR_factor_gt 0.2165 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 N1 N 0.80509(19) 0.64754(13) 0.79460(15) 0.0310(4) Uani 1 1 d . . . C2 C 0.7261(2) 0.71318(16) 0.79277(19) 0.0343(5) Uani 1 1 d . . . C3 C 0.7688(2) 0.79602(16) 0.79204(19) 0.0337(5) Uani 1 1 d . . . C4 C 0.8952(2) 0.81014(15) 0.79419(17) 0.0308(5) Uani 1 1 d . . . C5 C 0.9760(2) 0.74100(17) 0.7963(2) 0.0369(5) Uani 1 1 d . . . C6 C 0.9283(2) 0.66022(17) 0.7963(2) 0.0362(5) Uani 1 1 d . . . C7 C 0.9435(3) 0.89583(17) 0.7940(2) 0.0379(5) Uani 1 1 d . . . N8 N 0.9817(3) 0.96360(17) 0.7939(2) 0.0517(6) Uani 1 1 d . . . C9 C 0.7567(3) 0.55955(17) 0.7942(2) 0.0421(6) Uani 1 1 d . . . H2A H 0.6395 0.7026 0.7920 0.041 Uiso 1 1 calc R . . H3A H 0.7125 0.8426 0.7901 0.040 Uiso 1 1 calc R . . H5A H 1.0630 0.7498 0.7976 0.044 Uiso 1 1 calc R . . H6A H 0.9827 0.6126 0.7975 0.043 Uiso 1 1 calc R . . H9A H 0.6668 0.5608 0.7840 0.063 Uiso 1 1 calc R . . H9B H 0.7754 0.5322 0.8571 0.063 Uiso 1 1 calc R . . H9C H 0.7955 0.5272 0.7412 0.063 Uiso 1 1 calc R . . H11A H 0.6630 0.9551 0.5408 0.147 Uiso 1 1 calc R . . H11B H 0.6205 0.8782 0.6101 0.147 Uiso 1 1 calc R . . H11C H 0.6142 0.8679 0.4934 0.147 Uiso 1 1 calc R . . C1A C 0.6594(4) 0.0809(2) 0.8137(3) 0.0564(8) Uani 1 1 d . . . C2A C 0.6592(4) 0.3560(2) 0.6185(3) 0.0646(10) Uani 1 1 d . . . N3 N 0.7212(2) 0.22959(15) 0.7372(2) 0.0443(6) Uani 1 1 d . . . O1 O 0.5593(2) 0.13540(15) 0.65456(19) 0.0552(6) Uani 1 1 d . . . O2 O 0.7808(2) 0.09950(17) 0.65429(19) 0.0591(6) Uani 1 1 d . . . O3 O 0.5103(2) 0.29948(16) 0.7510(3) 0.0678(8) Uani 1 1 d . . . O4 O 0.6991(3) 0.37285(16) 0.8027(2) 0.0655(7) Uani 1 1 d . . . S1 S 0.67812(6) 0.13963(4) 0.69971(5) 0.0389(2) Uani 1 1 d . . . S2 S 0.63991(6) 0.31229(4) 0.74123(6) 0.0453(2) Uani 1 1 d . . . F1 F 0.6384(3) -0.00074(14) 0.7933(2) 0.0880(8) Uani 1 1 d . . . F2 F 0.5626(3) 0.10969(18) 0.8625(2) 0.0823(8) Uani 1 1 d . . . F3 F 0.7574(3) 0.08618(19) 0.8708(2) 0.0840(8) Uani 1 1 d . . . F4 F 0.7760(2) 0.37445(19) 0.6011(2) 0.0849(8) Uani 1 1 d . . . F5 F 0.6208(3) 0.30121(19) 0.5505(2) 0.0962(10) Uani 1 1 d . . . F6 F 0.5957(3) 0.42743(18) 0.6085(3) 0.1039(11) Uani 1 1 d . . . C1N C 0.7787(6) 0.8617(4) 0.5483(3) 0.0953(17) Uani 1 1 d . . . C2N C 0.8799(6) 0.9062(3) 0.5541(3) 0.0811(15) Uani 1 1 d . . . C3N C 1.0107(7) 0.8692(4) 0.5563(3) 0.0962(18) Uani 1 1 d . . . C4N C 1.0182(7) 0.7884(5) 0.5516(3) 0.111(2) Uani 1 1 d . . . C5N C 0.9289(5) 0.6435(4) 0.5391(3) 0.0808(13) Uani 1 1 d . . . C6N C 0.8291(5) 0.5911(2) 0.5315(3) 0.0681(11) Uani 1 1 d . . . C7N C 0.7127(5) 0.6249(4) 0.5294(3) 0.0773(13) Uani 1 1 d . . . C8N C 0.6896(5) 0.7092(4) 0.5345(3) 0.0841(14) Uani 1 1 d . . . C9N C 0.7904(5) 0.7639(3) 0.5416(2) 0.0717(12) Uani 1 1 d . . . C10N C 0.9075(5) 0.7355(4) 0.5438(2) 0.0809(16) Uani 1 1 d . . . C11N C 0.6608(6) 0.8930(4) 0.5481(4) 0.0980(17) Uani 1 1 d . . . H2NA H 0.8720 0.9665 0.5574 0.097 Uiso 1 1 calc R . . H3NA H 1.0820 0.9045 0.5609 0.115 Uiso 1 1 calc R . . H4NA H 1.0973 0.7620 0.5531 0.133 Uiso 1 1 calc R . . H5NA H 1.0105 0.6209 0.5414 0.097 Uiso 1 1 calc R . . H6NA H 0.8404 0.5311 0.5276 0.082 Uiso 1 1 calc R . . H7NA H 0.6444 0.5870 0.5240 0.093 Uiso 1 1 calc R . . H8NA H 0.6073 0.7306 0.5333 0.101 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 N1 0.0309(10) 0.0241(10) 0.0381(10) -0.0027(7) 0.0021(8) -0.0006(7) C2 0.0269(11) 0.0296(12) 0.0463(12) -0.0010(9) -0.0004(9) 0.0006(9) C3 0.0316(12) 0.0264(11) 0.0431(12) 0.0001(9) -0.0011(9) 0.0013(9) C4 0.0320(12) 0.0287(11) 0.0316(10) 0.0004(8) -0.0004(8) -0.0028(9) C5 0.0256(11) 0.0359(13) 0.0492(14) -0.0049(10) 0.0021(10) -0.0016(9) C6 0.0297(12) 0.0299(12) 0.0490(13) -0.0037(10) 0.0022(10) 0.0053(9) C7 0.0367(13) 0.0336(13) 0.0436(13) 0.0001(10) 0.0003(10) -0.0046(10) N8 0.0513(15) 0.0362(13) 0.0674(16) 0.0022(11) -0.0006(12) -0.0115(11) C9 0.0430(15) 0.0251(12) 0.0581(15) -0.0032(10) 0.0045(12) -0.0050(10) C1A 0.061(2) 0.0401(16) 0.068(2) 0.0050(14) 0.0080(16) 0.0010(14) C2A 0.059(2) 0.0397(17) 0.095(3) 0.0130(17) -0.0137(19) -0.0044(15) N3 0.0297(11) 0.0312(12) 0.0721(16) -0.0008(10) -0.0040(10) -0.0026(9) O1 0.0442(12) 0.0426(12) 0.0785(16) -0.0117(10) -0.0154(11) -0.0035(9) O2 0.0524(14) 0.0530(14) 0.0721(15) -0.0079(11) 0.0171(11) 0.0102(11) O3 0.0305(11) 0.0433(12) 0.130(2) -0.0191(14) 0.0127(12) -0.0025(9) O4 0.0618(16) 0.0402(12) 0.0946(19) -0.0183(12) -0.0034(13) -0.0123(11) S1 0.0332(4) 0.0298(3) 0.0536(4) -0.0028(2) 0.0025(3) 0.0008(2) S2 0.0307(4) 0.0282(3) 0.0769(5) -0.0066(3) 0.0008(3) -0.0046(2) F1 0.120(2) 0.0359(11) 0.108(2) 0.0106(11) 0.0183(17) -0.0076(12) F2 0.0838(18) 0.0805(17) 0.0831(16) 0.0025(13) 0.0401(14) 0.0005(14) F3 0.0926(19) 0.0845(18) 0.0745(15) 0.0182(13) -0.0188(13) 0.0114(15) F4 0.0696(16) 0.0838(18) 0.1014(19) 0.0289(15) 0.0096(14) -0.0151(13) F5 0.135(3) 0.0719(17) 0.0814(17) 0.0153(13) -0.0365(17) -0.0193(17) F6 0.095(2) 0.0540(15) 0.163(3) 0.0394(17) -0.024(2) 0.0124(14) C1N 0.110(4) 0.127(5) 0.048(2) 0.002(2) 0.001(2) 0.004(4) C2N 0.135(5) 0.061(2) 0.0480(18) -0.0012(16) -0.004(2) -0.031(3) C3N 0.147(6) 0.087(4) 0.054(2) -0.002(2) 0.002(3) -0.023(4) C4N 0.154(6) 0.121(5) 0.057(2) -0.008(3) 0.005(3) -0.066(4) C5N 0.091(3) 0.103(4) 0.0484(19) 0.003(2) 0.0014(19) 0.003(3) C6N 0.111(4) 0.0427(18) 0.0509(17) 0.0006(14) 0.0073(19) -0.001(2) C7N 0.089(3) 0.088(3) 0.055(2) 0.004(2) 0.0038(19) -0.028(3) C8N 0.090(3) 0.111(4) 0.051(2) 0.007(2) 0.004(2) 0.007(3) C9N 0.122(4) 0.061(2) 0.0328(14) -0.0001(13) 0.0063(18) 0.011(2) C10N 0.108(4) 0.101(4) 0.0331(15) -0.0010(17) 0.0022(18) -0.053(3) C11N 0.116(5) 0.120(5) 0.058(2) 0.004(3) 0.005(3) 0.017(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 N1 C2 1.337(3) . ? N1 C6 1.347(3) . ? N1 C9 1.475(3) . ? C3 C2 1.378(3) . ? C4 C3 1.384(3) . ? C4 C5 1.392(4) . ? C4 C7 1.441(3) . ? C5 C6 1.367(4) . ? N8 C7 1.140(4) . ? C1A F3 1.314(5) . ? S1 C1A 1.819(4) . ? S1 N3 1.570(2) . ? S1 O1 1.423(2) . ? S1 O2 1.420(2) . ? S2 C2A 1.822(5) . ? S2 N3 1.567(3) . ? S2 O3 1.422(2) . ? S2 O4 1.417(3) . ? F1 C1A 1.329(4) . ? F2 C1A 1.322(4) . ? F4 C2A 1.318(5) . ? F5 C2A 1.329(5) . ? F6 C2A 1.319(4) . ? C1N C11N 1.365(8) . ? C2N C1N 1.299(8) . ? C2N C3N 1.527(9) . ? C3N C4N 1.271(9) . ? C5N C6N 1.359(7) . ? C5N C10N 1.462(8) . ? C6N C7N 1.366(7) . ? C7N C8N 1.347(8) . ? C9N C1N 1.541(8) . ? C9N C8N 1.390(8) . ? C10N C4N 1.459(7) . ? C10N C9N 1.342(7) . ? 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 N1 C2 C3 120.7(2) . . ? N1 C6 C5 120.6(2) . . ? C2 C3 C4 118.8(2) . . ? C3 C4 C5 119.7(2) . . ? C3 C4 C7 120.4(2) . . ? C5 C4 C7 119.9(2) . . ? C6 C5 C4 119.0(2) . . ? C2 N1 C6 121.2(2) . . ? C2 N1 C9 119.5(2) . . ? C6 N1 C9 119.3(2) . . ? N8 C7 C4 180.0(4) . . ? N3 S1 C1A 102.12(16) . . ? N3 S2 C2A 102.25(17) . . ? S2 N3 S1 126.09(15) . . ? O1 S1 N3 116.64(13) . . ? O1 S1 C1A 104.02(17) . . ? O2 S1 O1 119.71(16) . . ? O2 S1 N3 108.00(15) . . ? O2 S1 C1A 103.86(16) . . ? O3 S2 N3 116.06(14) . . ? O3 S2 C2A 104.9(2) . . ? O4 S2 O3 118.72(17) . . ? O4 S2 N3 108.86(16) . . ? O4 S2 C2A 103.81(18) . . ? F1 C1A S1 109.2(3) . . ? F2 C1A F1 107.4(3) . . ? F2 C1A S1 110.5(3) . . ? F3 C1A S1 112.5(3) . . ? F3 C1A F1 108.7(3) . . ? F3 C1A F2 108.4(3) . . ? F4 C2A S2 111.2(3) . . ? F4 C2A F5 108.2(4) . . ? F4 C2A F6 107.1(3) . . ? F5 C2A S2 111.2(3) . . ? F6 C2A S2 110.6(4) . . ? F6 C2A F5 108.4(4) . . ? C1N C2N C3N 125.2(5) . . ? C2N C1N C11N 126.4(7) . . ? C2N C1N C9N 117.9(6) . . ? C3N C4N C10N 121.2(8) . . ? C4N C3N C2N 115.9(6) . . ? C4N C10N C5N 115.8(6) . . ? C5N C6N C7N 119.8(4) . . ? C6N C5N C10N 118.3(5) . . ? C7N C8N C9N 117.6(5) . . ? C8N C7N C6N 123.4(5) . . ? C8N C9N C1N 123.6(5) . . ? C9N C10N C4N 125.8(6) . . ? C9N C10N C5N 118.4(4) . . ? C10N C9N C1N 114.0(5) . . ? C10N C9N C8N 122.4(5) . . ? C11N C1N C9N 115.7(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 31.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.565 _refine_diff_density_min -0.932 _refine_diff_density_rms 0.249 #===end data_qub6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 F6 N3 O4 S2' _chemical_formula_weight 555.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.8851(13) _cell_length_b 15.9998(19) _cell_length_c 13.8814(17) _cell_angle_alpha 90.00 _cell_angle_beta 91.766(3) _cell_angle_gamma 90.00 _cell_volume 2416.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9423 _exptl_absorpt_correction_T_max 0.9706 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker Platinum 200 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17912 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.53 _reflns_number_total 3482 _reflns_number_gt 2856 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT v7.34a' _computing_data_reduction 'Bruker SAINT v7.34a' _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^)+(0.1212P)^2^+3.4541P] 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 contr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3482 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0734 _refine_ls_wR_factor_ref 0.2217 _refine_ls_wR_factor_gt 0.2094 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 N1 N 0.2981(3) 0.0980(2) 0.1921(2) 0.0475(8) Uani 1 1 d . . . C2 C 0.2214(4) 0.1633(3) 0.1897(3) 0.0510(10) Uani 1 1 d . . . C3 C 0.2648(4) 0.2432(3) 0.1867(3) 0.0521(11) Uani 1 1 d . . . C4 C 0.3902(4) 0.2564(3) 0.1858(3) 0.0483(10) Uani 1 1 d . . . C5 C 0.4674(4) 0.1884(3) 0.1876(3) 0.0599(12) Uani 1 1 d . . . C6 C 0.4197(4) 0.1093(3) 0.1909(3) 0.0573(11) Uani 1 1 d . . . C7 C 0.4394(4) 0.3405(3) 0.1861(3) 0.0588(12) Uani 1 1 d . . . N8 N 0.4797(4) 0.4060(3) 0.1888(3) 0.0752(12) Uani 1 1 d . . . C9 C 0.2465(4) 0.0115(3) 0.1941(3) 0.0577(11) Uani 1 1 d . . . C10 C 0.2072(5) -0.0165(3) 0.0952(4) 0.0710(14) Uani 1 1 d . . . H2A H 0.1352 0.1538 0.1900 0.061 Uiso 1 1 calc R . . H3A H 0.2095 0.2891 0.1854 0.063 Uiso 1 1 calc R . . H6A H 0.4732 0.0624 0.1924 0.069 Uiso 1 1 calc R . . H5A H 0.5539 0.1962 0.1865 0.072 Uiso 1 1 calc R . . H9A H 0.1750 0.0102 0.2366 0.069 Uiso 1 1 calc R . . H9B H 0.3094 -0.0274 0.2210 0.069 Uiso 1 1 calc R . . H10A H 0.1725 -0.0729 0.0984 0.107 Uiso 1 1 calc R . . H10B H 0.2785 -0.0170 0.0537 0.107 Uiso 1 1 calc R . . H10C H 0.1450 0.0220 0.0685 0.107 Uiso 1 1 calc R . . H11A H 0.1450 0.3973 0.4188 0.179 Uiso 1 1 calc R . . H11B H 0.1017 0.3215 0.4849 0.179 Uiso 1 1 calc R . . H11C H 0.0977 0.3120 0.3701 0.179 Uiso 1 1 calc R . . N3 N 0.7709(3) 0.1851(3) 0.2068(3) 0.0670(11) Uani 1 1 d . . . S1 S 0.81129(10) 0.09336(7) 0.18238(9) 0.0591(4) Uani 1 1 d . . . S2 S 0.85794(10) 0.26249(8) 0.21503(10) 0.0641(4) Uani 1 1 d . . . O1 O 0.9266(3) 0.0827(2) 0.1410(3) 0.0833(11) Uani 1 1 d . . . O2 O 0.7067(3) 0.0539(2) 0.1394(3) 0.0775(10) Uani 1 1 d . . . O3 O 0.8042(4) 0.3227(3) 0.2745(4) 0.1045(14) Uani 1 1 d . . . O4 O 0.9846(3) 0.2459(2) 0.2276(4) 0.1002(15) Uani 1 1 d . . . C1A C 0.8263(6) 0.0440(4) 0.3012(5) 0.0848(16) Uani 1 1 d . . . C2A C 0.8431(6) 0.3082(4) 0.0945(6) 0.0953(19) Uani 1 1 d . . . F1 F 0.7266(4) 0.0550(3) 0.3498(3) 0.1249(14) Uani 1 1 d . . . F2 F 0.9179(5) 0.0772(3) 0.3511(3) 0.1468(19) Uani 1 1 d . . . F3 F 0.8445(4) -0.0351(3) 0.2919(3) 0.1257(14) Uani 1 1 d . . . F4 F 0.9135(5) 0.3761(3) 0.0907(5) 0.1540(19) Uani 1 1 d . . . F5 F 0.7311(4) 0.3328(3) 0.0763(4) 0.1452(18) Uani 1 1 d . . . F6 F 0.8772(6) 0.2559(3) 0.0293(3) 0.1485(19) Uani 1 1 d . . . C1N C 0.2706(10) 0.3032(7) 0.4295(4) 0.123(3) Uani 1 1 d . . . C2N C 0.3678(8) 0.3493(4) 0.4256(4) 0.092(2) Uani 1 1 d . . . C3N C 0.4960(10) 0.3231(6) 0.4251(5) 0.121(3) Uani 1 1 d . . . C4N C 0.5099(8) 0.2292(7) 0.4282(5) 0.129(3) Uani 1 1 d . . . C5N C 0.4175(9) 0.0918(5) 0.4355(4) 0.110(2) Uani 1 1 d . . . C6N C 0.3213(9) 0.0433(5) 0.4408(4) 0.101(2) Uani 1 1 d . . . C7N C 0.2115(9) 0.0800(5) 0.4438(5) 0.107(2) Uani 1 1 d . . . C8N C 0.1783(7) 0.1594(6) 0.4412(4) 0.106(2) Uani 1 1 d . . . C9N C 0.2813(7) 0.2111(5) 0.4347(4) 0.094(2) Uani 1 1 d . . . C10N C 0.3994(6) 0.1873(5) 0.4336(3) 0.0841(18) Uani 1 1 d . . . C11N C 0.1428(8) 0.3363(5) 0.4255(5) 0.120(3) Uani 1 1 d . . . H2NA H 0.3539 0.4078 0.4228 0.111 Uiso 1 1 calc R . . H3NA H 0.5632 0.3608 0.4231 0.145 Uiso 1 1 calc R . . H4NA H 0.5872 0.2017 0.4265 0.155 Uiso 1 1 calc R . . H5NA H 0.4976 0.0685 0.4328 0.132 Uiso 1 1 calc R . . H6NA H 0.3293 -0.0159 0.4424 0.122 Uiso 1 1 calc R . . H7NA H 0.1449 0.0420 0.4487 0.129 Uiso 1 1 calc R . . H8NA H 0.0959 0.1786 0.4434 0.127 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 N1 0.048(2) 0.053(2) 0.0406(18) 0.0030(15) -0.0012(14) 0.0024(16) C2 0.040(2) 0.062(3) 0.051(2) 0.003(2) 0.0009(17) 0.000(2) C3 0.046(2) 0.056(3) 0.054(3) 0.002(2) -0.0003(18) 0.0050(19) C4 0.048(2) 0.059(3) 0.037(2) 0.0024(18) -0.0001(17) -0.0051(19) C5 0.039(2) 0.080(3) 0.060(3) 0.000(2) 0.0003(19) -0.004(2) C6 0.045(2) 0.067(3) 0.060(3) 0.002(2) -0.0009(19) 0.012(2) C7 0.050(2) 0.081(4) 0.046(2) 0.005(2) -0.0008(19) -0.004(2) N8 0.076(3) 0.074(3) 0.075(3) 0.008(2) 0.000(2) -0.021(2) C9 0.065(3) 0.054(3) 0.054(3) 0.008(2) 0.000(2) -0.001(2) C10 0.100(4) 0.056(3) 0.056(3) 0.001(2) -0.008(3) -0.002(3) N3 0.046(2) 0.064(3) 0.091(3) -0.015(2) 0.0043(19) 0.0031(18) S1 0.0566(7) 0.0573(7) 0.0638(7) -0.0127(5) 0.0072(5) -0.0032(5) S2 0.0446(7) 0.0578(7) 0.0891(9) -0.0204(6) -0.0083(6) 0.0055(5) O1 0.066(2) 0.074(2) 0.112(3) -0.018(2) 0.026(2) 0.0041(17) O2 0.069(2) 0.081(2) 0.082(2) -0.0075(19) -0.0095(18) -0.0097(18) O3 0.105(3) 0.080(3) 0.129(4) -0.045(3) 0.004(3) 0.017(2) O4 0.052(2) 0.079(3) 0.167(4) -0.026(3) -0.026(2) 0.0024(18) C1A 0.086(4) 0.080(4) 0.087(4) 0.004(3) -0.010(3) -0.003(3) C2A 0.090(4) 0.084(4) 0.112(5) 0.009(4) 0.008(4) -0.008(4) F1 0.146(4) 0.139(4) 0.092(3) 0.015(2) 0.043(3) 0.003(3) F2 0.155(4) 0.167(4) 0.114(3) 0.022(3) -0.069(3) -0.044(3) F3 0.155(4) 0.080(3) 0.141(4) 0.027(2) -0.015(3) 0.016(2) F4 0.155(4) 0.100(3) 0.207(5) 0.042(3) 0.016(4) -0.028(3) F5 0.129(4) 0.147(4) 0.157(4) 0.041(3) -0.045(3) 0.021(3) F6 0.216(6) 0.132(4) 0.101(3) 0.005(3) 0.043(3) -0.005(4) C1N 0.163(8) 0.160(8) 0.047(3) -0.019(4) -0.001(4) 0.015(7) C2N 0.124(6) 0.095(5) 0.057(3) -0.007(3) -0.005(3) -0.040(4) C3N 0.161(8) 0.144(8) 0.059(4) 0.012(4) 0.001(4) 0.003(6) C4N 0.119(6) 0.199(10) 0.070(4) -0.016(5) -0.003(4) 0.047(6) C5N 0.160(7) 0.112(6) 0.058(4) 0.010(4) -0.012(4) -0.010(5) C6N 0.158(7) 0.078(4) 0.067(4) 0.007(3) 0.002(4) 0.005(5) C7N 0.166(8) 0.086(5) 0.070(4) -0.002(3) 0.004(4) 0.035(5) C8N 0.102(5) 0.156(7) 0.059(4) -0.014(4) 0.003(3) -0.030(5) C9N 0.124(6) 0.113(5) 0.045(3) -0.002(3) -0.001(3) 0.030(4) C10N 0.076(4) 0.136(6) 0.040(3) 0.005(3) -0.007(2) -0.027(4) C11N 0.167(8) 0.115(6) 0.075(4) -0.012(4) -0.022(4) 0.021(5) _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 N1 C6 1.337(5) . ? N1 C2 1.337(5) . ? N1 C9 1.494(5) . ? C2 C3 1.364(6) . ? C4 C5 1.375(6) . ? C4 C3 1.382(6) . ? C4 C7 1.447(7) . ? C6 C5 1.368(7) . ? C7 N8 1.137(6) . ? C9 C10 1.495(7) . ? S1 N3 1.571(4) . ? S1 O1 1.407(3) . ? S1 O2 1.417(3) . ? S1 C1A 1.832(6) . ? S2 N3 1.561(4) . ? S2 O3 1.408(4) . ? S2 O4 1.409(4) . ? S2 C2A 1.829(8) . ? F1 C1A 1.307(7) . ? F2 C1A 1.309(7) . ? F3 C1A 1.288(7) . ? F4 C2A 1.331(7) . ? F5 C2A 1.298(7) . ? F6 C2A 1.296(8) . ? C1N C11N 1.488(11) . ? C2N C1N 1.293(11) . ? C2N C3N 1.456(11) . ? C4N C3N 1.510(12) . ? C5N C6N 1.308(10) . ? C6N C7N 1.333(10) . ? C8N C7N 1.321(10) . ? C9N C8N 1.399(10) . ? C9N C1N 1.479(12) . ? C10N C4N 1.382(11) . ? C10N C5N 1.540(10) . ? C10N C9N 1.342(9) . ? 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 N1 C2 C3 121.1(4) . . ? N1 C6 C5 120.2(4) . . ? N1 C9 C10 110.9(4) . . ? C2 N1 C9 119.3(3) . . ? C2 C3 C4 119.1(4) . . ? C3 C4 C7 120.5(4) . . ? C5 C4 C3 118.8(4) . . ? C5 C4 C7 120.6(4) . . ? C6 N1 C2 120.8(4) . . ? C6 N1 C9 119.9(4) . . ? C6 C5 C4 120.0(4) . . ? N3 S1 C1A 103.1(3) . . ? N3 S2 C2A 102.4(3) . . ? N8 C7 C4 178.0(5) . . ? O1 S1 C1A 105.0(3) . . ? O1 S1 O2 119.3(2) . . ? O1 S1 N3 117.4(2) . . ? O2 S1 C1A 103.6(3) . . ? O2 S1 N3 106.3(2) . . ? O3 S2 C2A 103.6(3) . . ? O3 S2 N3 108.9(3) . . ? O3 S2 O4 118.6(3) . . ? O4 S2 C2A 104.3(3) . . ? O4 S2 N3 116.6(2) . . ? S2 N3 S1 125.7(2) . . ? F1 C1A S1 110.7(4) . . ? F1 C1A F2 107.6(6) . . ? F2 C1A S1 110.3(5) . . ? F3 C1A F1 108.5(6) . . ? F3 C1A S1 110.1(5) . . ? F3 C1A F2 109.6(6) . . ? F4 C2A S2 109.1(5) . . ? F5 C2A S2 110.8(5) . . ? F5 C2A F4 106.5(6) . . ? F6 C2A S2 111.2(5) . . ? F6 C2A F4 108.8(6) . . ? F6 C2A F5 110.3(7) . . ? C1N C2N C3N 128.4(8) . . ? C2N C1N C9N 120.5(9) . . ? C2N C1N C11N 124.1(10) . . ? C2N C3N C4N 112.4(8) . . ? C4N C10N C5N 111.8(7) . . ? C5N C6N C7N 117.4(8) . . ? C6N C5N C10N 119.2(8) . . ? C7N C8N C9N 110.6(8) . . ? C8N C7N C6N 131.9(9) . . ? C8N C9N C1N 122.1(8) . . ? C9N C1N C11N 115.4(8) . . ? C9N C10N C4N 134.3(8) . . ? C9N C10N C5N 113.9(6) . . ? C10N C9N C1N 110.9(8) . . ? C10N C4N C3N 113.4(8) . . ? C10N C9N C8N 127.0(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.53 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.423 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.071 #===end