# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef 'Compound7_VFFereira.cif' _publ_section_related_literature ? _publ_requested_category ? _publ_section_abstract ; (type here to add abstract) ; #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2010-06-26 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ; ? 2010-08-11 # Formatted by publCIF ; #============================================================================== # # SUBMISSION DETAILS _publ_contact_author_name 'Vitor F. Ferreira' # Name of author for correspondence _publ_contact_author_address ; Departamento de Qu\'imica Org\\^anica Instituto de Qu\'imica Universidade Federal Fluminense Niter\'oi, RJ Brasil ; # Address of author for correspondence _publ_contact_author_email cegvito@vm.uff.br _publ_contact_author_fax 00(000)0000000 _publ_contact_author_phone 55(21)26292345 _publ_contact_letter ; Submission dated :2010-12-14 Please consider this CIF for submission to the Cambridge Crystallographic Data Centre. I certify that all authors have seen and approved of this submission, that all have made significant scientific contributions to the work reported, and that all share responsibility and accountability for the results. This CIF is submitted as a personal communication This CIF is submitted as part of a journal submission Organic & Biomolecular Chemistry Ferreira, Vitor F. ; #============================================================================== # # TITLE AND AUTHOR LIST _publ_section_title ; Synthesis of new 9-hydroxy-\a and 7-hydroxy-\b-pyran naphthoquinones and cytotoxicity against cancer cell lines ; _publ_section_title_footnote . # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address _publ_author_footnote D.R.d.Rocha ; Departamento de Qu\'imica Org\\^anica Instituto de Qu\'imica Universidade Federal Fluminense Niter\'oi, RJ Brasil ; . A.C.G.d.Souza ; Departamento de Qu\'imica Org\\^anica Instituto de Qu\'imica Universidade Federal Fluminense Niter\'oi, RJ Brasil ; . J.A.L.C.Resende ; Departamento de Qu\'imica Inorg\\^anica Instituto de Qu\'imica Universidade Federal Fluminense Niter\'oi, RJ Brasil ; . W.C.Santos ; Faculdade de F\'armacia Universidade Federal Fluminense Niter\'oi, RJ Brasil ; . E.A.d.Santos ; Laborat\'orio de Oncologia Experimental, Departamento de Fisiologia e Farmacologia Universidade Federal do Cear\'a Fortaleza, CE ; . C.Pessoa ; Laborat\'orio de Oncologia Experimental, Departamento de Fisiologia e Farmacologia Universidade Federal do Cear\'a Fortaleza, CE ; . M.O.d.Moraes ; Laborat\'orio de Oncologia Experimental, Departamento de Fisiologia e Farmacologia Universidade Federal do Cear\'a Fortaleza, CE ; . L.V.Costa-Lotufo ; Laborat\'orio de Oncologia Experimental, Departamento de Fisiologia e Farmacologia Universidade Federal do Cear\'a Fortaleza, CE ; . R.C.Montenegro ; Laborat\'orio de Oncologia Experimental, Departamento de Fisiologia e Farmacologia Universidade Federal do Cear\'a Fortaleza, CE ; . V.F.Ferreira ; Departamento de Qu\'imica Org\\^anica Instituto de Qu\'imica Universidade Federal Fluminense Niter\'oi, RJ Brasil ; . #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_compound7 _database_code_depnum_ccdc_archive 'CCDC 811449' #TrackingRef 'Compound7_VFFereira.cif' _audit_creation_date 2010-06-26T15:54:25-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 5-hydroxy-2-(p-tolylthio)naphthalene-1,4-dione ; _chemical_name_common 'Compound 7' _chemical_formula_moiety 'C17 H12 O3 S1' _chemical_formula_sum 'C17 H12 O3 S1' _chemical_formula_weight 296.34 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.713(2) _cell_length_b 11.179(2) _cell_length_c 13.663(3) _cell_angle_alpha 90 _cell_angle_beta 109.59(3) _cell_angle_gamma 90 _cell_volume 1397.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8729 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 25.01 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 -2 0 0.068 -1 2 0 0.062 -1 -2 -1 0.088 -2 0 -1 0.072 2 0 1 0.052 1 2 1 0.043 1 0 -2 0.02 -1 0 2 0.03 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.238 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_T_max 0.991 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_number 8729 _diffrn_reflns_av_R_equivalents 0.0919 _diffrn_reflns_av_sigmaI/netI 0.0849 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_full 25.02 _reflns_number_total 2473 _reflns_number_gt 1267 _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0607P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.011(2) _refine_ls_number_reflns 2473 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1224 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1104 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.951 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.162 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.045 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 0.16898(12) 0.34914(9) 0.11173(6) 0.0810(4) Uani 1 1 d . . . O4 O 0.5140(3) 0.7014(2) 0.16246(16) 0.0707(7) Uani 1 1 d . . . C4A C 0.3936(3) 0.6447(3) -0.0124(2) 0.0474(8) Uani 1 1 d . . . O1 O 0.1475(3) 0.3950(2) -0.09592(16) 0.0784(8) Uani 1 1 d . . . O5 O 0.5459(3) 0.8172(2) 0.01005(19) 0.0879(9) Uani 1 1 d . . . H5 H 0.5534 0.8042 0.0707 0.132 Uiso 1 1 calc R . . C1 C 0.2299(4) 0.4683(3) -0.0398(2) 0.0538(8) Uani 1 1 d . . . C3 C 0.3563(3) 0.5391(3) 0.1379(2) 0.0505(8) Uani 1 1 d . . . H3 H 0.3769 0.5317 0.2092 0.061 Uiso 1 1 calc R . . C8A C 0.2989(3) 0.5639(3) -0.0808(2) 0.0495(8) Uani 1 1 d . . . C4 C 0.4268(3) 0.6329(3) 0.1002(2) 0.0521(8) Uani 1 1 d . . . C2 C 0.2628(3) 0.4624(3) 0.0750(2) 0.0511(8) Uani 1 1 d . . . C11 C 0.2237(4) 0.3708(3) 0.2473(2) 0.0528(8) Uani 1 1 d . . . C12 C 0.3281(4) 0.3000(3) 0.3124(3) 0.0652(9) Uani 1 1 d . . . H12 H 0.3712 0.2402 0.2852 0.078 Uiso 1 1 calc R . . C16 C 0.1601(4) 0.4565(3) 0.2886(3) 0.0668(10) Uani 1 1 d . . . H16 H 0.0873 0.5049 0.2451 0.080 Uiso 1 1 calc R . . C5 C 0.4553(4) 0.7367(3) -0.0516(3) 0.0598(9) Uani 1 1 d . . . C14 C 0.3104(4) 0.4014(3) 0.4606(2) 0.0611(9) Uani 1 1 d . . . C8 C 0.2696(4) 0.5740(3) -0.1859(2) 0.0661(10) Uani 1 1 d . . . H8 H 0.2085 0.5193 -0.2314 0.079 Uiso 1 1 calc R . . C6 C 0.4223(4) 0.7472(3) -0.1578(3) 0.0685(10) Uani 1 1 d . . . H6 H 0.4619 0.8098 -0.1846 0.082 Uiso 1 1 calc R . . C7 C 0.3324(4) 0.6670(4) -0.2235(3) 0.0713(11) Uani 1 1 d . . . H7 H 0.3128 0.6745 -0.2947 0.086 Uiso 1 1 calc R . . C15 C 0.2030(4) 0.4714(3) 0.3940(3) 0.0706(10) Uani 1 1 d . . . H15 H 0.1585 0.5303 0.4211 0.085 Uiso 1 1 calc R . . C13 C 0.3705(4) 0.3154(3) 0.4175(3) 0.0722(11) Uani 1 1 d . . . H13 H 0.4422 0.2658 0.4606 0.087 Uiso 1 1 calc R . . C17 C 0.3597(5) 0.4202(4) 0.5768(3) 0.1075(16) Uani 1 1 d . . . H17A H 0.2854 0.4628 0.5945 0.161 Uiso 1 1 calc R . . H17B H 0.4486 0.4658 0.5984 0.161 Uiso 1 1 calc R . . H17C H 0.3763 0.3441 0.6112 0.161 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 0.1133(8) 0.0842(7) 0.0440(5) -0.0087(5) 0.0244(5) -0.0495(6) O4 0.0770(16) 0.0754(16) 0.0556(14) -0.0102(12) 0.0167(13) -0.0282(14) C4A 0.0513(19) 0.0493(18) 0.0445(17) 0.0028(15) 0.0197(15) 0.0086(16) O1 0.1023(19) 0.0866(17) 0.0392(12) -0.0136(12) 0.0143(12) -0.0358(15) O5 0.111(2) 0.0799(19) 0.0846(18) -0.0066(15) 0.0477(18) -0.0373(17) C1 0.060(2) 0.061(2) 0.0358(17) -0.0051(16) 0.0105(16) -0.0047(18) C3 0.059(2) 0.0560(19) 0.0316(16) 0.0018(15) 0.0093(15) -0.0054(17) C8A 0.054(2) 0.057(2) 0.0392(17) 0.0059(16) 0.0178(15) 0.0047(17) C4 0.0538(19) 0.054(2) 0.0472(18) -0.0032(16) 0.0154(16) -0.0030(17) C2 0.061(2) 0.0552(19) 0.0358(17) 0.0021(15) 0.0139(16) -0.0052(17) C11 0.065(2) 0.052(2) 0.0421(17) 0.0031(16) 0.0185(17) -0.0120(18) C12 0.079(3) 0.060(2) 0.066(2) 0.0064(19) 0.036(2) 0.010(2) C16 0.073(2) 0.065(2) 0.058(2) 0.0133(18) 0.0168(19) 0.015(2) C5 0.065(2) 0.056(2) 0.063(2) 0.0073(18) 0.0291(19) 0.0003(19) C14 0.071(2) 0.073(2) 0.0418(18) 0.0050(18) 0.0215(18) -0.015(2) C8 0.072(2) 0.085(3) 0.0396(19) 0.0038(18) 0.0169(17) 0.000(2) C6 0.079(3) 0.067(2) 0.070(3) 0.017(2) 0.039(2) 0.010(2) C7 0.077(3) 0.096(3) 0.046(2) 0.025(2) 0.027(2) 0.021(2) C15 0.090(3) 0.065(2) 0.066(2) -0.004(2) 0.039(2) 0.009(2) C13 0.071(2) 0.087(3) 0.056(2) 0.023(2) 0.0167(19) 0.019(2) C17 0.135(4) 0.141(4) 0.046(2) -0.011(2) 0.029(2) -0.042(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 1.730(3) . ? S1 C11 1.764(3) . ? O4 C4 1.242(3) . ? C4A C5 1.386(4) . ? C4A C8A 1.400(4) . ? C4A C4 1.468(4) . ? O1 C1 1.220(3) . ? O5 C5 1.340(4) . ? O5 H5 0.8200 . ? C1 C8A 1.468(4) . ? C1 C2 1.494(4) . ? C3 C2 1.332(4) . ? C3 C4 1.439(4) . ? C3 H3 0.9300 . ? C8A C8 1.373(4) . ? C11 C12 1.357(4) . ? C11 C16 1.361(4) . ? C12 C13 1.366(4) . ? C12 H12 0.9300 . ? C16 C15 1.368(4) . ? C16 H16 0.9300 . ? C5 C6 1.383(4) . ? C14 C13 1.358(5) . ? C14 C15 1.376(5) . ? C14 C17 1.511(4) . ? C8 C7 1.388(5) . ? C8 H8 0.9300 . ? C6 C7 1.359(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C15 H15 0.9300 . ? C13 H13 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C11 101.62(14) . . ? C5 C4A C8A 119.6(3) . . ? C5 C4A C4 120.0(3) . . ? C8A C4A C4 120.4(3) . . ? C5 O5 H5 109.5 . . ? O1 C1 C8A 122.5(3) . . ? O1 C1 C2 119.6(3) . . ? C8A C1 C2 117.9(3) . . ? C2 C3 C4 122.8(3) . . ? C2 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? C8 C8A C4A 120.3(3) . . ? C8 C8A C1 119.9(3) . . ? C4A C8A C1 119.8(3) . . ? O4 C4 C3 120.1(3) . . ? O4 C4 C4A 121.5(3) . . ? C3 C4 C4A 118.5(3) . . ? C3 C2 C1 120.5(3) . . ? C3 C2 S1 126.6(2) . . ? C1 C2 S1 112.9(2) . . ? C12 C11 C16 118.8(3) . . ? C12 C11 S1 120.3(3) . . ? C16 C11 S1 120.8(3) . . ? C11 C12 C13 120.8(3) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C11 C16 C15 120.1(3) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? O5 C5 C6 118.4(3) . . ? O5 C5 C4A 122.2(3) . . ? C6 C5 C4A 119.4(3) . . ? C13 C14 C15 117.2(3) . . ? C13 C14 C17 121.5(4) . . ? C15 C14 C17 121.3(4) . . ? C8A C8 C7 119.1(3) . . ? C8A C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C7 C6 C5 120.6(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 121.0(3) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C16 C15 C14 121.6(3) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C14 C13 C12 121.6(3) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C4A C8A C8 1.4(4) . . . . ? C4 C4A C8A C8 -179.0(3) . . . . ? C5 C4A C8A C1 -178.3(3) . . . . ? C4 C4A C8A C1 1.3(4) . . . . ? O1 C1 C8A C8 0.9(5) . . . . ? C2 C1 C8A C8 -178.8(3) . . . . ? O1 C1 C8A C4A -179.4(3) . . . . ? C2 C1 C8A C4A 0.9(4) . . . . ? C2 C3 C4 O4 -179.5(3) . . . . ? C2 C3 C4 C4A 0.3(5) . . . . ? C5 C4A C4 O4 -2.6(5) . . . . ? C8A C4A C4 O4 177.8(3) . . . . ? C5 C4A C4 C3 177.6(3) . . . . ? C8A C4A C4 C3 -2.0(4) . . . . ? C4 C3 C2 C1 2.0(5) . . . . ? C4 C3 C2 S1 -178.3(2) . . . . ? O1 C1 C2 C3 177.7(3) . . . . ? C8A C1 C2 C3 -2.6(5) . . . . ? O1 C1 C2 S1 -2.0(4) . . . . ? C8A C1 C2 S1 177.7(2) . . . . ? C11 S1 C2 C3 3.0(3) . . . . ? C11 S1 C2 C1 -177.3(2) . . . . ? C2 S1 C11 C12 -101.3(3) . . . . ? C2 S1 C11 C16 80.3(3) . . . . ? C16 C11 C12 C13 -1.1(5) . . . . ? S1 C11 C12 C13 -179.5(3) . . . . ? C12 C11 C16 C15 1.0(5) . . . . ? S1 C11 C16 C15 179.5(3) . . . . ? C8A C4A C5 O5 179.5(3) . . . . ? C4 C4A C5 O5 -0.1(5) . . . . ? C8A C4A C5 C6 0.0(5) . . . . ? C4 C4A C5 C6 -179.6(3) . . . . ? C4A C8A C8 C7 -1.5(5) . . . . ? C1 C8A C8 C7 178.2(3) . . . . ? O5 C5 C6 C7 179.2(3) . . . . ? C4A C5 C6 C7 -1.3(5) . . . . ? C5 C6 C7 C8 1.2(5) . . . . ? C8A C8 C7 C6 0.2(5) . . . . ? C11 C16 C15 C14 0.0(5) . . . . ? C13 C14 C15 C16 -1.1(5) . . . . ? C17 C14 C15 C16 178.6(3) . . . . ? C15 C14 C13 C12 1.0(5) . . . . ? C17 C14 C13 C12 -178.6(3) . . . . ? C11 C12 C13 C14 0.0(5) . . . . ? 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 O5 H5 O4 0.82 1.83 2.557(3) 146.5 . # END of CIF # Attachment 'compound8_VFFereira.cif' data_compound8 _database_code_depnum_ccdc_archive 'CCDC 811450' #TrackingRef 'compound8_VFFereira.cif' _audit_creation_date 2010-12-14T15:55:47-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 8-hydroxy-2-(p-tolylthio)naphthalene-1,4-dione ; _chemical_formula_moiety 'C17 H12 O3 S1' _chemical_formula_sum 'C17 H12 O3 S1' _chemical_formula_weight 296.33 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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' _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _cell_length_a 8.9234(7) _cell_length_b 8.6499(7) _cell_length_c 17.8425(8) _cell_angle_alpha 90 _cell_angle_beta 103.821(7) _cell_angle_gamma 90 _cell_volume 1337.33(16) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 1797 _cell_measurement_theta_min 2.5469 _cell_measurement_theta_max 62.2802 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.207 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.90767 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 10.4186 _diffrn_orient_matrix_ub_11 -0.0836618 _diffrn_orient_matrix_ub_12 0.1023278 _diffrn_orient_matrix_ub_13 0.047513 _diffrn_orient_matrix_ub_21 -0.1567217 _diffrn_orient_matrix_ub_22 -0.0499378 _diffrn_orient_matrix_ub_23 -0.0515398 _diffrn_orient_matrix_ub_31 -0.0055426 _diffrn_orient_matrix_ub_32 -0.1361195 _diffrn_orient_matrix_ub_33 0.0545862 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_unetI/netI 0.0269 _diffrn_reflns_number 3625 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.11 _diffrn_reflns_theta_max 60.26 _diffrn_reflns_theta_full 60.26 _diffrn_measured_fraction_theta_full 0.94 _diffrn_measured_fraction_theta_max 0.94 _reflns_number_total 1872 _reflns_number_gt 1518 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0529P)^2^+0.4095P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1872 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.212 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.51154(6) 0.85539(7) 0.23171(3) 0.0277(2) Uani 1 1 d . . . C11 C 0.3354(3) 0.8812(2) 0.25993(12) 0.0230(5) Uani 1 1 d . . . O1 O 0.75213(17) 0.89691(17) 0.16032(9) 0.0301(4) Uani 1 1 d . . . O4 O 0.28125(18) 1.26513(19) 0.02934(9) 0.0357(4) Uani 1 1 d . . . C14 C 0.0753(3) 0.8973(3) 0.32087(13) 0.0259(5) Uani 1 1 d . . . C4 C 0.3924(3) 1.1862(2) 0.06091(13) 0.0251(5) Uani 1 1 d . . . C8A C 0.6651(2) 1.0991(2) 0.07187(12) 0.0223(5) Uani 1 1 d . . . O8 O 0.92842(17) 1.02219(19) 0.08022(9) 0.0335(4) Uani 1 1 d . . . H8 H 0.9057 0.9611 0.1124 0.050 Uiso 1 1 calc R . . C4A C 0.5422(3) 1.1977(2) 0.03801(12) 0.0230(5) Uani 1 1 d . . . C1 C 0.6486(2) 0.9888(2) 0.13046(12) 0.0234(5) Uani 1 1 d . . . C7 C 0.8209(3) 1.2203(3) -0.00579(13) 0.0299(6) Uani 1 1 d . . . H7 H 0.9150 1.2280 -0.0216 0.036 Uiso 1 1 calc R . . C8 C 0.8054(3) 1.1111(3) 0.04924(13) 0.0257(5) Uani 1 1 d . . . C5 C 0.5595(3) 1.3055(2) -0.01582(12) 0.0265(5) Uani 1 1 d . . . H5 H 0.4763 1.3720 -0.0385 0.032 Uiso 1 1 calc R . . C12 C 0.3262(3) 0.9920(3) 0.31484(13) 0.0269(5) Uani 1 1 d . . . H12 H 0.4086 1.0630 0.3319 0.032 Uiso 1 1 calc R . . C2 C 0.5011(2) 0.9877(2) 0.15627(12) 0.0225(5) Uani 1 1 d . . . C6 C 0.7004(3) 1.3167(3) -0.03707(13) 0.0291(6) Uani 1 1 d . . . H6 H 0.7125 1.3924 -0.0738 0.035 Uiso 1 1 calc R . . C16 C 0.2136(3) 0.7802(3) 0.23511(13) 0.0286(5) Uani 1 1 d . . . H16 H 0.2187 0.7047 0.1971 0.034 Uiso 1 1 calc R . . C13 C 0.1969(3) 0.9992(3) 0.34472(13) 0.0270(5) Uani 1 1 d . . . H13 H 0.1915 1.0754 0.3823 0.032 Uiso 1 1 calc R . . C3 C 0.3821(3) 1.0782(2) 0.12286(12) 0.0235(5) Uani 1 1 d . . . H3 H 0.2890 1.0723 0.1397 0.028 Uiso 1 1 calc R . . C15 C 0.0854(3) 0.7880(3) 0.26479(13) 0.0286(6) Uani 1 1 d . . . H15 H 0.0025 0.7180 0.2469 0.034 Uiso 1 1 calc R . . C17 C -0.0633(3) 0.9022(3) 0.35463(15) 0.0352(6) Uani 1 1 d . . . H17A H -0.1552 0.9271 0.3140 0.053 Uiso 1 1 calc R . . H17C H -0.0482 0.9815 0.3950 0.053 Uiso 1 1 calc R . . H17B H -0.0770 0.8013 0.3770 0.053 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 0.0276(3) 0.0316(3) 0.0267(3) 0.0081(2) 0.0120(2) 0.0047(3) C11 0.0255(13) 0.0231(12) 0.0209(11) 0.0054(9) 0.0062(9) 0.0015(9) O1 0.0272(9) 0.0331(9) 0.0319(9) 0.0071(7) 0.0107(7) 0.0072(7) O4 0.0353(10) 0.0382(10) 0.0370(10) 0.0115(8) 0.0153(8) 0.0133(8) C14 0.0240(13) 0.0290(13) 0.0241(12) 0.0102(10) 0.0046(10) 0.0040(10) C4 0.0300(13) 0.0227(12) 0.0243(12) -0.0019(9) 0.0095(10) 0.0038(10) C8A 0.0270(13) 0.0204(11) 0.0200(11) -0.0036(9) 0.0068(10) -0.0025(9) O8 0.0287(9) 0.0394(10) 0.0359(10) 0.0049(8) 0.0148(7) 0.0037(8) C4A 0.0288(12) 0.0203(12) 0.0209(11) -0.0056(9) 0.0081(10) -0.0033(9) C1 0.0248(13) 0.0243(12) 0.0215(12) -0.0049(9) 0.0065(10) -0.0015(10) C7 0.0339(14) 0.0334(13) 0.0263(13) -0.0043(10) 0.0148(11) -0.0069(11) C8 0.0269(13) 0.0270(13) 0.0238(12) -0.0052(9) 0.0075(10) -0.0025(10) C5 0.0370(14) 0.0234(12) 0.0204(12) -0.0007(9) 0.0092(10) 0.0007(10) C12 0.0283(13) 0.0258(13) 0.0271(13) 0.0007(10) 0.0077(10) -0.0043(10) C2 0.0255(12) 0.0218(12) 0.0211(12) -0.0034(9) 0.0075(10) -0.0037(10) C6 0.0427(15) 0.0256(13) 0.0220(12) 0.0005(9) 0.0135(11) -0.0069(11) C16 0.0332(14) 0.0273(13) 0.0254(12) -0.0017(10) 0.0071(10) -0.0031(11) C13 0.0317(14) 0.0232(12) 0.0270(12) -0.0007(9) 0.0090(10) 0.0025(10) C3 0.0243(12) 0.0256(12) 0.0228(12) -0.0012(9) 0.0101(10) 0.0006(10) C15 0.0245(13) 0.0297(13) 0.0305(14) -0.0001(10) 0.0040(10) -0.0069(10) C17 0.0270(14) 0.0421(15) 0.0382(14) 0.0082(12) 0.0114(11) 0.0059(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 1.752(2) . ? S1 C11 1.775(2) . ? C11 C16 1.382(3) . ? C11 C12 1.388(3) . ? O1 C1 1.238(2) . ? O4 C4 1.225(3) . ? C14 C13 1.384(3) . ? C14 C15 1.395(3) . ? C14 C17 1.500(3) . ? C4 C3 1.466(3) . ? C4 C4A 1.492(3) . ? C8A C4A 1.407(3) . ? C8A C8 1.408(3) . ? C8A C1 1.449(3) . ? O8 C8 1.346(3) . ? O8 H8 0.8400 . ? C4A C5 1.373(3) . ? C1 C2 1.495(3) . ? C7 C6 1.370(3) . ? C7 C8 1.393(3) . ? C7 H7 0.9500 . ? C5 C6 1.401(3) . ? C5 H5 0.9500 . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C2 C3 1.339(3) . ? C6 H6 0.9500 . ? C16 C15 1.372(3) . ? C16 H16 0.9500 . ? C13 H13 0.9500 . ? C3 H3 0.9500 . ? C15 H15 0.9500 . ? C17 H17A 0.9800 . ? C17 H17C 0.9800 . ? C17 H17B 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C11 104.33(10) . . ? C16 C11 C12 119.2(2) . . ? C16 C11 S1 120.77(17) . . ? C12 C11 S1 119.55(17) . . ? C13 C14 C15 118.1(2) . . ? C13 C14 C17 121.3(2) . . ? C15 C14 C17 120.5(2) . . ? O4 C4 C3 120.8(2) . . ? O4 C4 C4A 121.1(2) . . ? C3 C4 C4A 118.05(19) . . ? C4A C8A C8 119.2(2) . . ? C4A C8A C1 120.4(2) . . ? C8 C8A C1 120.4(2) . . ? C8 O8 H8 109.5 . . ? C5 C4A C8A 120.4(2) . . ? C5 C4A C4 119.6(2) . . ? C8A C4A C4 119.98(19) . . ? O1 C1 C8A 122.6(2) . . ? O1 C1 C2 119.00(19) . . ? C8A C1 C2 118.37(19) . . ? C6 C7 C8 120.0(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? O8 C8 C7 117.9(2) . . ? O8 C8 C8A 122.3(2) . . ? C7 C8 C8A 119.8(2) . . ? C4A C5 C6 119.6(2) . . ? C4A C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C13 C12 C11 119.9(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C3 C2 C1 121.47(19) . . ? C3 C2 S1 127.96(17) . . ? C1 C2 S1 110.57(15) . . ? C7 C6 C5 121.0(2) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C15 C16 C11 120.6(2) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C12 C13 C14 121.2(2) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C2 C3 C4 121.5(2) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C16 C15 C14 120.9(2) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? H17C C17 H17B 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 S1 C11 C16 100.13(19) . . . . ? C2 S1 C11 C12 -87.80(18) . . . . ? C8 C8A C4A C5 -0.7(3) . . . . ? C1 C8A C4A C5 178.02(19) . . . . ? C8 C8A C4A C4 179.66(18) . . . . ? C1 C8A C4A C4 -1.6(3) . . . . ? O4 C4 C4A C5 4.2(3) . . . . ? C3 C4 C4A C5 -175.32(19) . . . . ? O4 C4 C4A C8A -176.1(2) . . . . ? C3 C4 C4A C8A 4.3(3) . . . . ? C4A C8A C1 O1 178.00(19) . . . . ? C8 C8A C1 O1 -3.3(3) . . . . ? C4A C8A C1 C2 -2.7(3) . . . . ? C8 C8A C1 C2 175.98(19) . . . . ? C6 C7 C8 O8 -177.91(19) . . . . ? C6 C7 C8 C8A 0.7(3) . . . . ? C4A C8A C8 O8 178.85(18) . . . . ? C1 C8A C8 O8 0.1(3) . . . . ? C4A C8A C8 C7 0.3(3) . . . . ? C1 C8A C8 C7 -178.41(19) . . . . ? C8A C4A C5 C6 0.1(3) . . . . ? C4 C4A C5 C6 179.73(19) . . . . ? C16 C11 C12 C13 0.8(3) . . . . ? S1 C11 C12 C13 -171.38(16) . . . . ? O1 C1 C2 C3 -176.1(2) . . . . ? C8A C1 C2 C3 4.6(3) . . . . ? O1 C1 C2 S1 3.4(2) . . . . ? C8A C1 C2 S1 -175.87(15) . . . . ? C11 S1 C2 C3 -5.2(2) . . . . ? C11 S1 C2 C1 175.31(14) . . . . ? C8 C7 C6 C5 -1.3(3) . . . . ? C4A C5 C6 C7 0.9(3) . . . . ? C12 C11 C16 C15 -0.7(3) . . . . ? S1 C11 C16 C15 171.45(17) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C15 C14 C13 C12 -0.9(3) . . . . ? C17 C14 C13 C12 178.4(2) . . . . ? C1 C2 C3 C4 -1.9(3) . . . . ? S1 C2 C3 C4 178.68(16) . . . . ? O4 C4 C3 C2 177.9(2) . . . . ? C4A C4 C3 C2 -2.5(3) . . . . ? C11 C16 C15 C14 -0.3(3) . . . . ? C13 C14 C15 C16 1.1(3) . . . . ? C17 C14 C15 C16 -178.3(2) . . . . ? 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 O8 H8 O1 0.84 1.86 2.601(2) 145.6 . # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF