# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dekker, Frank' _publ_contact_author_email f.j.dekker@rug.nl _publ_section_title ; Isothiazolones; thiol-reactive inhibitors of the histone acetyl transferase PCAF and cysteine protease Cathepsin B ; loop_ _publ_author_name R.Wisastra M.Ghizzoni A.J.Minnaard H.Maarsingh H.Haisma ; F.Dekker ; data_q1569 _database_code_depnum_ccdc_archive 'CCDC 763228' #TrackingRef 'q1569.cif' #============================================================================== # 0. AUDIT DETAILS _audit_creation_date '2009-10-27 08:14:40' _audit_creation_method ; PLATON option (version :: 300909) SHELXL97-2 & Manual Editing ; _audit_update_record ; ? 2010-01-25 # Formatted by publCIF ; #=============================================================================== # 4. TEXT _publ_section_synopsis . _publ_section_abstract ; (type here to add abstract) ; # Insert blank lines between paragraphs _publ_section_comment ; (type here to add) ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; All hydrogen atoms were located in a difference Fourier map and refined with isotropic displacement parameters. C---H distances were in the range of 0.91 -- 0.99(3) \%A. ; _publ_section_related_literature ; ; # Insert blank lines between references _publ_section_references ; Bruker, (2007). SMART (Version 5.632), SAINT-Plus (Version 7.46a) and SADABS (Version 2.10). Bruker AXS Inc., Madison, Wisconsin, USA. Meetsma, A. (2009). Extended version of the program PLUTO. University of Groningen, The Netherlands. (unpublished). Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. Spek, A. L. (2003). J. Appl. Cryst.36, 7--13. ; _publ_section_figure_captions ; Fig. 1. Perspective PLUTO drawings of the molecule illustrating the configuration and the adopted numbering scheme. Fig. 2. Molecular packing viewed down unit cell axes. Fig. 3. Perspective ORTEP drawing of the title compound. Displacement ellipsoids for non-H atoms are represented at the 50% probability level. The H-atoms are drawn with an arbitrary radius. ; _publ_section_acknowledgements ; ? ; #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H6 Cl N O S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C9 H6 Cl N O S' _chemical_formula_iupac ? _chemical_formula_weight 211.67 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z 5 -x,-y,-z 6 1/2+x,y,1/2-z 7 1/2-x,1/2+y,z 8 x,1/2-y,1/2+z _cell_length_a 13.912(3) _cell_length_b 5.9518(12) _cell_length_c 21.173(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1753.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 3992 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.91 _cell_special_details ; The final unit cell was obtained from the xyz centroids of 3992 reflections after integration using the SAINTPLUS software package (Bruker, 2007). Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the final atomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988) ; _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.625 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS, (Bruker, 2007))' _exptl_absorpt_correction_T_min 0.7649 _exptl_absorpt_correction_T_max 0.9394 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed Siemens Mo tube ' _diffrn_radiation_monochromator 'parallel mounted graphite' _diffrn_radiation_detector ; CCD area-detector ; _diffrn_measurement_device_type ; Bruker Smart Apex; CCD area detector ; _diffrn_measurement_method '\f and \w scans' _diffrn_special_details ; Crystal into the cold nitrogen stream of the low-temparature unit (KRYOFLEX, (Bruker, 2007)). ; _diffrn_detector_area_resol_mean 66.06 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 14622 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 28.28 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; Intensity data were corrected for Lorentz and polarization effects, decay and absorption and reduced to F~o~^2^ using SAINT-Plus & SADABS (Bruker, 2007). ; # number of unique reflections _reflns_number_total 2168 _reflns_number_gt 1801 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2007)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2007)' _computing_data_reduction SAINT-Plus _computing_structure_solution ; SHELXS-97 (Sheldrick, 2008) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; PLATON (Spek, 2003) PLUTO (Meetsma, 2009) ; _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0519P)^2^+0.8096P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary direct _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _chemical_absolute_configuration . _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2168 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.409 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.069 _vrn_publ_code_number_frames 1800 _vrn_publ_code_frame_time_sec 10.0 _vrn_publ_code_meas_time_hour 7.8 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cl Cl Uani 0.17092(3) 0.44509(8) 0.59628(2) 1.0 0.0263(2) . . S S Uani 0.16876(3) 0.37608(7) 0.45906(2) 1.0 0.0205(1) . . O O Uani 0.02924(9) 0.8986(2) 0.41276(6) 1.0 0.0228(4) . . N N Uani 0.11372(11) 0.5653(2) 0.41070(7) 1.0 0.0185(4) . . C1 C Uani 0.13737(13) 0.5391(3) 0.52330(8) 1.0 0.0198(5) . . C2 C Uani 0.08770(12) 0.7262(3) 0.50887(9) 1.0 0.0201(5) . . C3 C Uani 0.07209(12) 0.7489(3) 0.44129(8) 1.0 0.0187(5) . . C4 C Uani 0.11732(12) 0.5358(3) 0.34355(8) 1.0 0.0171(5) . . C5 C Uani 0.15529(12) 0.7083(3) 0.30646(9) 1.0 0.0201(5) . . C6 C Uani 0.15666(12) 0.6820(3) 0.24151(9) 1.0 0.0215(5) . . C7 C Uani 0.12153(13) 0.4857(3) 0.21387(9) 1.0 0.0213(5) . . C8 C Uani 0.08561(12) 0.3135(3) 0.25157(8) 1.0 0.0205(5) . . C9 C Uani 0.08293(12) 0.3376(3) 0.31681(9) 1.0 0.0192(5) . . H1 H Uiso 0.0614(16) 0.824(4) 0.5386(10) 1.0 0.029(6) . . H5 H Uiso 0.1760(12) 0.837(3) 0.3250(9) 1.0 0.013(5) . . H6 H Uiso 0.1830(15) 0.798(4) 0.2171(10) 1.0 0.032(6) . . H7 H Uiso 0.1207(14) 0.471(3) 0.1683(10) 1.0 0.020(5) . . H8 H Uiso 0.0605(15) 0.181(4) 0.2323(10) 1.0 0.024(5) . . H9 H Uiso 0.0570(13) 0.217(3) 0.3445(9) 1.0 0.021(5) . . 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 Cl 0.0349(3) 0.0265(3) 0.0174(2) 0.0037(2) -0.0047(2) -0.0010(2) S 0.0255(3) 0.0179(2) 0.0182(2) 0.0004(2) -0.0033(2) 0.0042(2) O 0.0269(7) 0.0192(6) 0.0223(7) 0.0001(5) -0.0009(5) 0.0053(5) N 0.0233(7) 0.0164(7) 0.0159(8) 0.0002(5) -0.0015(5) 0.0034(5) C1 0.0228(9) 0.0207(8) 0.0159(9) 0.0007(6) -0.0019(7) -0.0039(7) C2 0.0211(8) 0.0195(8) 0.0196(9) -0.0023(7) 0.0021(7) -0.0017(7) C3 0.0175(8) 0.0167(8) 0.0218(9) -0.0013(7) 0.0004(7) -0.0002(6) C4 0.0167(8) 0.0190(8) 0.0157(8) -0.0007(6) -0.0011(6) 0.0027(6) C5 0.0187(8) 0.0183(9) 0.0234(9) -0.0005(7) -0.0020(7) -0.0014(6) C6 0.0188(8) 0.0225(9) 0.0231(9) 0.0050(7) 0.0020(7) 0.0002(7) C7 0.0194(8) 0.0280(9) 0.0165(9) -0.0008(7) 0.0005(6) 0.0043(7) C8 0.0190(8) 0.0187(8) 0.0237(10) -0.0046(7) -0.0011(7) 0.0013(6) C9 0.0177(8) 0.0173(8) 0.0226(9) 0.0005(7) -0.0012(7) 0.0002(6) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl C1 1.7084(18) . . yes S N 1.7038(15) . . yes S C1 1.7269(18) . . yes O C3 1.231(2) . . yes N C3 1.396(2) . . yes N C4 1.433(2) . . yes C1 C2 1.346(3) . . no C2 C3 1.454(3) . . no C4 C5 1.396(3) . . no C4 C9 1.393(3) . . no C5 C6 1.384(3) . . no C6 C7 1.395(3) . . no C7 C8 1.392(3) . . no C8 C9 1.389(3) . . no C2 H1 0.93(2) . . no C5 H5 0.908(18) . . no C6 H6 0.94(2) . . no C7 H7 0.97(2) . . no C8 H8 0.95(2) . . no C9 H9 0.995(18) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N S C1 89.33(8) . . . yes S N C3 115.15(12) . . . yes S N C4 119.96(11) . . . yes C3 N C4 124.79(14) . . . yes Cl C1 S 117.34(10) . . . yes Cl C1 C2 128.07(14) . . . yes S C1 C2 114.58(14) . . . yes C1 C2 C3 112.16(16) . . . no O C3 N 122.68(15) . . . yes O C3 C2 128.53(16) . . . yes N C3 C2 108.78(15) . . . yes N C4 C5 118.75(15) . . . yes N C4 C9 119.66(15) . . . yes C5 C4 C9 121.60(16) . . . no C4 C5 C6 118.74(16) . . . no C5 C6 C7 120.44(17) . . . no C6 C7 C8 120.12(17) . . . no C7 C8 C9 120.25(16) . . . no C4 C9 C8 118.83(16) . . . no C1 C2 H1 124.4(14) . . . no C3 C2 H1 123.2(14) . . . no C4 C5 H5 119.8(12) . . . no C6 C5 H5 121.4(12) . . . no C5 C6 H6 118.0(14) . . . no C7 C6 H6 121.5(14) . . . no C6 C7 H7 119.8(11) . . . no C8 C7 H7 120.0(11) . . . no C7 C8 H8 119.7(13) . . . no C9 C8 H8 120.0(13) . . . no C4 C9 H9 119.7(11) . . . no C8 C9 H9 121.4(11) . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 S N C3 0.00(14) . . . . no C1 S N C4 176.51(14) . . . . no N S C1 Cl 179.46(11) . . . . no N S C1 C2 0.17(15) . . . . no S N C3 O -179.48(14) . . . . no S N C3 C2 -0.19(18) . . . . no C4 N C3 O 4.2(3) . . . . no C4 N C3 C2 -176.49(15) . . . . no S N C4 C5 -123.01(15) . . . . no S N C4 C9 57.2(2) . . . . no C3 N C4 C5 53.1(2) . . . . no C3 N C4 C9 -126.70(18) . . . . no Cl C1 C2 C3 -179.50(14) . . . . no S C1 C2 C3 -0.3(2) . . . . no C1 C2 C3 O 179.55(18) . . . . no C1 C2 C3 N 0.3(2) . . . . no N C4 C5 C6 -178.48(15) . . . . no C9 C4 C5 C6 1.3(3) . . . . no N C4 C9 C8 178.99(15) . . . . no C5 C4 C9 C8 -0.8(3) . . . . no C4 C5 C6 C7 -0.6(3) . . . . no C5 C6 C7 C8 -0.6(3) . . . . no C6 C7 C8 C9 1.2(3) . . . . no C7 C8 C9 C4 -0.4(3) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl O 3.4605(15) . 5_566 no Cl C7 3.639(2) . 8_555 no Cl H6 2.99(2) . 8_565 no Cl H7 2.991(19) . 8_555 no S S 3.7370(10) . 7_555 no S C2 3.6826(19) . 5_566 no S S 3.7370(10) . 7_545 no S C1 3.626(2) . 7_545 no S C2 3.6589(19) . 7_545 no S H9 3.033(19) . . no O C5 3.070(2) . . no O C9 3.393(2) . 1_565 no O Cl 3.4605(15) . 5_566 no O C2 3.223(2) . 5_576 no O H7 2.74(2) . 4_555 no O H5 2.785(18) . . no O H9 2.414(18) . 1_565 no O H1 2.32(2) . 5_576 no C1 C2 3.572(3) . 5_566 no C1 C3 3.463(3) . 5_566 no C1 S 3.626(2) . 7_555 no C2 S 3.6826(19) . 5_566 no C2 O 3.223(2) . 5_576 no C2 C1 3.572(3) . 5_566 no C2 S 3.6589(19) . 7_555 no C3 C1 3.463(3) . 5_566 no C5 O 3.070(2) . . no C6 C8 3.463(2) . 4_555 no C7 Cl 3.639(2) . 8_554 no C7 C9 3.592(3) . 4_555 no C7 C8 3.556(3) . 4_555 no C8 C6 3.463(2) . 4_545 no C8 C7 3.556(3) . 4_545 no C9 C7 3.592(3) . 4_545 no C9 O 3.393(2) . 1_545 no C3 H5 2.903(19) . . no C4 H8 3.07(2) . 4_555 no C6 H8 3.07(2) . 4_555 no C7 H6 2.94(2) . 7_545 no C7 H8 3.01(2) . 4_555 no C7 H9 3.097(18) . 4_555 no C8 H8 3.01(2) . 4_555 no C9 H8 3.04(2) . 4_555 no H1 O 2.32(2) . 5_576 no H5 O 2.785(18) . . no H5 C3 2.903(19) . . no H6 C7 2.94(2) . 7_555 no H6 Cl 2.99(2) . 8_564 no H7 O 2.74(2) . 4_545 no H7 Cl 2.991(19) . 8_554 no H8 C4 3.07(2) . 4_545 no H8 C6 3.07(2) . 4_545 no H8 C7 3.01(2) . 4_545 no H8 C8 3.01(2) . 4_545 no H8 C9 3.04(2) . 4_545 no H9 S 3.033(19) . . no H9 O 2.414(18) . 1_545 no H9 C7 3.097(18) . 4_545 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C2 H1 O 0.93(2) 2.32(2) 3.223(2) 163.3(19) 5_576 yes C9 H9 O 0.995(18) 2.414(18) 3.393(2) 167.8(15) 1_545 yes data_q1570 _database_code_depnum_ccdc_archive 'CCDC 763229' #TrackingRef 'q1570.cif' #============================================================================== # 0. AUDIT DETAILS _audit_creation_date '2009-10-27 16:16:27' _audit_creation_method ; PLATON
option (version :: 300909) SHELXL97-2 & Manual Editing ; _audit_update_record ; ? 2010-01-25 # Formatted by publCIF ; #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H7 N O S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C9 H7 N O S' _chemical_formula_iupac ? _chemical_formula_weight 177.23 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 17.363(19) _cell_length_b 6.389(7) _cell_length_c 7.471(8) _cell_angle_alpha 90 _cell_angle_beta 95.868(18) _cell_angle_gamma 90 _cell_volume 824.4(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 1437 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 25.08 _cell_special_details ; The final unit cell was obtained from the xyz centroids of 1437 reflections after integration using the SAINTPLUS software package (Bruker, 2007). Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the final atomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988) ; _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.02 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS, (Bruker, 2007))' _exptl_absorpt_correction_T_min 0.8791 _exptl_absorpt_correction_T_max 0.9900 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed Siemens Mo tube ' _diffrn_radiation_monochromator 'parallel mounted graphite' _diffrn_radiation_detector ; CCD area-detector ; _diffrn_measurement_device_type ; Bruker Smart Apex; CCD area detector ; _diffrn_measurement_method '\f and \w scans' _diffrn_special_details ; Crystal into the cold nitrogen stream of the low-temparature unit (KRYOFLEX, (Bruker, 2007)). ; _diffrn_detector_area_resol_mean 66.06 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 4894 _diffrn_reflns_av_R_equivalents 0.0957 _diffrn_reflns_av_sigmaI/netI 0.0943 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 23.82 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.82 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; Intensity data were corrected for Lorentz and polarization effects, decay and absorption and reduced to F~o~^2^ using SAINT-Plus & SADABS (Bruker, 2007). ; # number of unique reflections _reflns_number_total 1270 _reflns_number_gt 920 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2007)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2007)' _computing_data_reduction SAINT-Plus _computing_structure_solution ; DIRDIF-08 (Beurskens et al., 2008) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; PLATON (Spek, 2003) PLUTO (Meetsma, 2009) ; _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.1140P)^2^+0.7626P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1270 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.1081 _refine_ls_R_factor_gt 0.0767 _refine_ls_wR_factor_ref 0.2014 _refine_ls_wR_factor_gt 0.1824 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.312 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.133 _vrn_publ_code_number_frames 1800 _vrn_publ_code_frame_time_sec 10.0 _vrn_publ_code_meas_time_hour 7.8 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags S S Uani 0.17419(8) 0.07046(18) 0.33877(15) 1.0 0.0253(5) . . O O Uani 0.1166(2) 0.6419(5) 0.3879(4) 1.0 0.0287(13) . . N N Uani 0.1856(3) 0.3371(6) 0.3433(5) 1.0 0.0228(14) . . C1 C Uani 0.0803(3) 0.0975(7) 0.3815(6) 1.0 0.0257(18) . . C2 C Uani 0.0579(3) 0.2974(7) 0.3985(6) 1.0 0.0226(18) . . C3 C Uani 0.1190(3) 0.4479(7) 0.3774(6) 1.0 0.0212(18) . . C4 C Uani 0.2608(3) 0.4235(7) 0.3276(6) 1.0 0.0240(18) . . C5 C Uani 0.2681(3) 0.6121(7) 0.2358(6) 1.0 0.0268(18) . . C6 C Uani 0.3414(3) 0.6890(8) 0.2184(7) 1.0 0.0323(19) . . C7 C Uani 0.4076(4) 0.5819(9) 0.2876(7) 1.0 0.043(2) . . C8 C Uani 0.3990(4) 0.3925(9) 0.3781(7) 1.0 0.041(2) . . C9 C Uani 0.3270(3) 0.3139(9) 0.4009(6) 1.0 0.0313(19) . . H1 H Uiso 0.04675 -0.01825 0.39228 1.0 0.0307 . . H2 H Uiso 0.00712 0.33628 0.42202 1.0 0.0272 . . H5 H Uiso 0.22347 0.68613 0.18633 1.0 0.0322 . . H6 H Uiso 0.34662 0.81811 0.15772 1.0 0.0386 . . H7 H Uiso 0.45764 0.63598 0.27372 1.0 0.0512 . . H8 H Uiso 0.44378 0.31704 0.42456 1.0 0.0493 . . H9 H Uiso 0.32196 0.18726 0.46533 1.0 0.0377 . . 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 S 0.0439(11) 0.0162(8) 0.0159(7) -0.0020(4) 0.0037(6) 0.0035(6) O 0.045(3) 0.0153(19) 0.0267(19) -0.0006(14) 0.0084(18) 0.0018(16) N 0.038(3) 0.016(2) 0.015(2) -0.0010(16) 0.005(2) 0.002(2) C1 0.044(4) 0.023(3) 0.009(2) 0.0019(19) -0.002(2) -0.008(2) C2 0.035(4) 0.017(3) 0.017(2) -0.0001(19) 0.008(2) 0.001(2) C3 0.037(4) 0.018(3) 0.008(2) 0.0014(18) -0.001(2) 0.004(2) C4 0.042(4) 0.023(3) 0.008(2) -0.0065(19) 0.007(2) -0.001(3) C5 0.049(4) 0.023(3) 0.009(2) -0.0060(19) 0.006(2) 0.000(3) C6 0.045(4) 0.037(3) 0.016(3) -0.001(2) 0.008(3) -0.008(3) C7 0.048(4) 0.056(4) 0.025(3) 0.003(3) 0.008(3) -0.011(3) C8 0.046(4) 0.053(4) 0.025(3) 0.003(3) 0.006(3) 0.006(3) C9 0.044(4) 0.037(3) 0.013(3) 0.003(2) 0.004(3) 0.004(3) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S N 1.715(4) . . yes S C1 1.702(6) . . yes O C3 1.243(6) . . yes N C3 1.401(7) . . yes N C4 1.433(7) . . yes C1 C2 1.345(7) . . no C2 C3 1.452(7) . . no C4 C5 1.399(7) . . no C4 C9 1.408(7) . . no C5 C6 1.383(7) . . no C6 C7 1.391(8) . . no C7 C8 1.402(8) . . no C8 C9 1.374(9) . . no C1 H1 0.95 . . no C2 H2 0.95 . . no C5 H5 0.95 . . no C6 H6 0.95 . . no C7 H7 0.95 . . no C8 H8 0.95 . . no C9 H9 0.95 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N S C1 90.4(2) . . . yes S N C3 114.2(4) . . . yes S N C4 119.0(4) . . . yes C3 N C4 126.6(4) . . . yes S C1 C2 114.0(4) . . . yes C1 C2 C3 113.4(5) . . . no O C3 N 123.3(5) . . . yes O C3 C2 128.6(5) . . . yes N C3 C2 108.1(4) . . . yes N C4 C5 120.1(4) . . . yes N C4 C9 119.4(4) . . . yes C5 C4 C9 120.5(5) . . . no C4 C5 C6 118.9(5) . . . no C5 C6 C7 121.6(5) . . . no C6 C7 C8 118.6(6) . . . no C7 C8 C9 121.2(6) . . . no C4 C9 C8 119.1(5) . . . no S C1 H1 123 . . . no C2 C1 H1 123 . . . no C1 C2 H2 123 . . . no C3 C2 H2 123 . . . no C4 C5 H5 121 . . . no C6 C5 H5 121 . . . no C5 C6 H6 119 . . . no C7 C6 H6 119 . . . no C6 C7 H7 121 . . . no C8 C7 H7 121 . . . no C7 C8 H8 119 . . . no C9 C8 H8 119 . . . no C4 C9 H9 120 . . . no C8 C9 H9 120 . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 S N C3 0.2(3) . . . . no C1 S N C4 175.2(3) . . . . no N S C1 C2 0.1(4) . . . . no S N C3 O 179.1(3) . . . . no S N C3 C2 -0.3(5) . . . . no C4 N C3 O 4.5(7) . . . . no C4 N C3 C2 -174.9(4) . . . . no S N C4 C5 144.9(4) . . . . no S N C4 C9 -33.3(5) . . . . no C3 N C4 C5 -40.7(6) . . . . no C3 N C4 C9 141.0(5) . . . . no S C1 C2 C3 -0.2(5) . . . . no C1 C2 C3 O -179.0(5) . . . . no C1 C2 C3 N 0.4(5) . . . . no N C4 C5 C6 -178.2(4) . . . . no C9 C4 C5 C6 0.0(7) . . . . no N C4 C9 C8 177.0(4) . . . . no C5 C4 C9 C8 -1.3(7) . . . . no C4 C5 C6 C7 0.9(7) . . . . no C5 C6 C7 C8 -0.5(8) . . . . no C6 C7 C8 C9 -0.8(8) . . . . no C7 C8 C9 C4 1.7(8) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S O 2.951(5) . 1_545 no S C5 3.476(6) . 1_545 no S C5 3.439(6) . 4_555 no S C3 3.484(6) . 4_554 no S H9 2.75 . . no S H5 2.87 . 1_545 no S H5 3.12 . 4_555 no O S 2.951(5) . 1_565 no O C1 2.978(6) . 1_565 no O C5 2.976(7) . . no O H1 2.49 . 1_565 no O H5 2.52 . . no O H2 2.70 . 3_566 no C1 O 2.978(6) . 1_545 no C1 C2 3.575(8) . 2_545 no C2 C1 3.575(8) . 2_555 no C3 S 3.484(6) . 4_555 no C5 S 3.439(6) . 4_554 no C5 O 2.976(7) . . no C5 S 3.476(6) . 1_565 no C1 H1 2.96 . 3_556 no C1 H2 3.09 . 2_545 no C2 H2 2.98 . 3_566 no C2 H1 3.08 . 3_556 no C2 H1 2.93 . 2_555 no C3 H5 2.86 . . no C4 H9 3.09 . 4_554 no C5 H9 3.00 . 4_554 no C6 H9 3.06 . 4_554 no C8 H6 3.00 . 4_565 no C9 H6 3.03 . 4_565 no H1 O 2.49 . 1_545 no H1 C2 2.93 . 2_545 no H1 C1 2.96 . 3_556 no H1 C2 3.08 . 3_556 no H1 H1 2.41 . 3_556 no H2 C1 3.09 . 2_555 no H2 O 2.70 . 3_566 no H2 C2 2.98 . 3_566 no H2 H2 2.42 . 3_566 no H5 S 2.87 . 1_565 no H5 O 2.52 . . no H5 C3 2.86 . . no H5 S 3.12 . 4_554 no H6 C8 3.00 . 4_564 no H6 C9 3.03 . 4_564 no H9 S 2.75 . . no H9 C4 3.09 . 4_555 no H9 C5 3.00 . 4_555 no H9 C6 3.06 . 4_555 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C1 H1 O 0.9500 2.4900 2.978(6) 112 1_545 yes C5 H5 S 0.9500 2.8700 3.476(6) 122 1_565 yes C5 H5 O 0.9500 2.5200 2.976(7) 109 . yes C9 H9 S 0.9500 2.7500 3.070(6) 101 . yes #===END of Crystallographic Information File