# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full MedChemComm _journal_coden_cambridge 1476 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_footnote _publ_author_address A.Gelain ; ? ; ;Department of Pharmaceutical Chemistry "P.Pratesi" University of Milano via L. Mangiagalli, 25 20133-Milano, Italy ; L.Legnani '' '' S.Villa '' '' D.Masciocchi '' '' F.Meneghetti '' '' A.Pedretti '' '' D.Barlocco '' '' L.Toma '' '' B.-M.Kwon '' '' A.Asai '' '' S.Nakano '' '' _publ_contact_author_address ; Department of Pharmaceutical and Chemistry "P.Pratesi" University of Milano via L. Mangiagalli, 25 20133-Milano, Italy ; _publ_contact_author_email fiorella.meneghetti@unimi.it _publ_contact_author_fax '+39 2 50319359' _publ_contact_author_phone '+39 2 50319306' #============================================================================== # # SUBMISSION DETAILS _publ_contact_author_name 'Meneghetti, Fiorella' _publ_contact_letter ; Submission dated :2011-12-06 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 Meneghetti, Fiorella. ; #============================================================================== # # TITLE AND AUTHOR LIST _publ_section_title ; ? ; data_1 _database_code_depnum_ccdc_archive 'CCDC 853297' #TrackingRef '- CCDC_MD77.cif' #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2011-12-06 _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 ? _publ_section_title_footnote ; ? ; #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_sum 'C16 H9 Cl F3 N3 O2' _chemical_formula_weight 367.71 _exptl_crystal_description platelet _exptl_crystal_colour white #============================================================================== # CRYSTAL DATA loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 11.115(3) _cell_length_b 5.008(3) _cell_length_c 14.112(5) _cell_angle_alpha 90 _cell_angle_beta 92.280(10) _cell_angle_gamma 90 _cell_volume 784.9(6) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.292 _exptl_absorpt_correction_type none _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 10 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1 _diffrn_reflns_number 1925 _diffrn_reflns_av_R_equivalents 0.0937 _diffrn_reflns_av_unetI/netI 0.2392 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 16 #============================================================================== # STRUCTURE SOLUTION loop_ _computing_data_collection 'CAD-4 Software (Enraf Nonius, 1989)' _computing_cell_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # 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. ; _reflns_number_total 1549 _reflns_number_gt 532 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.2155 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.0571 _refine_ls_goodness_of_fit_ref 0.846 _refine_ls_restrained_S_all 0.845 _refine_ls_number_reflns 1549 _refine_ls_number_parameters 190 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_mean 0.007 _refine_diff_density_max 0.273 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.079 _refine_ls_extinction_method none 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' Cl Cl 0.1484 0.1585 '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 Cl1 Cl -0.5741(2) 0.6886(5) 0.3981(2) 0.0962(13) Uani 1 1 d . . . O2 O -0.0431(5) 0.2693(10) 0.5217(5) 0.0436(9) Uani 1 1 d . . . F3 F 0.2162(6) 0.0851(14) 0.0948(4) 0.094(2) Uani 1 1 d . . . N2 N -0.1047(7) -0.2826(14) 0.6852(6) 0.049(2) Uani 1 1 d . . . N3 N -0.0768(6) -0.1700(13) 0.5296(5) 0.0436(9) Uani 1 1 d . . . H3 H -0.0690 -0.3210 0.5015 0.052 Uiso 1 1 calc R . . O1 O -0.1862(7) -0.2256(13) 0.7569(5) 0.061(2) Uani 1 1 d . . . F2 F 0.3685(5) -0.0234(13) 0.1814(4) 0.091(2) Uani 1 1 d . . . C8 C 0.1822(8) -0.053(2) 0.2519(6) 0.039(3) Uani 1 1 d . . . C5 C 0.0437(9) 0.0056(19) 0.4059(7) 0.0436(9) Uani 1 1 d . . . C7 C 0.2074(8) 0.1498(19) 0.3146(7) 0.0436(9) Uani 1 1 d . . . H7 H 0.2703 0.2677 0.3047 0.052 Uiso 1 1 calc R . . F1 F 0.2518(6) -0.3174(13) 0.1249(5) 0.108(3) Uani 1 1 d . . . N1 N -0.2706(7) -0.0451(18) 0.7192(7) 0.059(3) Uani 1 1 d . . . C11 C -0.0277(9) 0.0515(17) 0.4921(7) 0.0436(9) Uani 1 1 d . . . C2 C -0.1409(8) -0.1580(19) 0.6144(7) 0.0436(9) Uani 1 1 d . . . C6 C 0.1361(7) 0.1763(19) 0.3940(7) 0.050(3) Uani 1 1 d . . . H6 H 0.1524 0.3106 0.4382 0.060 Uiso 1 1 calc R . . C1 C -0.2410(8) 0.010(2) 0.6335(8) 0.047(3) Uani 1 1 d . . . C3 C -0.3156(8) 0.187(2) 0.5728(8) 0.044(3) Uani 1 1 d . . . C18 C 0.2540(11) -0.071(2) 0.1641(8) 0.058(4) Uani 1 1 d . . . C13 C -0.3261(9) 0.153(2) 0.4745(7) 0.053(3) Uani 1 1 d . . . H13 H -0.2795 0.0265 0.4447 0.063 Uiso 1 1 calc R . . C16 C -0.4653(8) 0.5269(19) 0.5608(8) 0.047(3) Uani 1 1 d . . . H16 H -0.5149 0.6509 0.5890 0.057 Uiso 1 1 calc R . . C17 C -0.3879(9) 0.377(2) 0.6186(8) 0.054(3) Uani 1 1 d . . . H17 H -0.3834 0.3999 0.6840 0.064 Uiso 1 1 calc R . . C14 C -0.4050(9) 0.308(2) 0.4224(7) 0.065(3) Uani 1 1 d . . . H14 H -0.4136 0.2823 0.3572 0.078 Uiso 1 1 calc R . . C9 C 0.0868(9) -0.2215(17) 0.2626(8) 0.0436(9) Uani 1 1 d . . . H9 H 0.0691 -0.3542 0.2181 0.052 Uiso 1 1 calc R . . C15 C -0.4723(8) 0.502(2) 0.4651(8) 0.050(3) Uani 1 1 d . . . C10 C 0.0180(8) -0.1905(19) 0.3405(8) 0.057(3) Uani 1 1 d . . . H10 H -0.0469 -0.3040 0.3490 0.068 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 Cl1 0.082(2) 0.0600(17) 0.143(3) 0.009(3) -0.041(2) 0.011(2) O2 0.054(2) 0.0156(13) 0.062(2) 0.002(2) 0.0093(18) 0.0018(19) F3 0.120(6) 0.105(6) 0.058(5) 0.026(5) 0.005(4) 0.018(5) N2 0.082(6) 0.021(4) 0.046(5) 0.013(5) 0.010(5) 0.000(5) N3 0.054(2) 0.0156(13) 0.062(2) 0.002(2) 0.0093(18) 0.0018(19) O1 0.087(5) 0.056(6) 0.040(5) 0.022(5) 0.006(4) -0.013(5) F2 0.059(4) 0.150(6) 0.067(4) 0.004(5) 0.029(4) -0.010(5) C8 0.047(7) 0.036(7) 0.033(6) 0.000(6) 0.012(5) 0.004(6) C5 0.054(2) 0.0156(13) 0.062(2) 0.002(2) 0.0093(18) 0.0018(19) C7 0.054(2) 0.0156(13) 0.062(2) 0.002(2) 0.0093(18) 0.0018(19) F1 0.172(7) 0.057(5) 0.102(6) -0.039(5) 0.079(5) -0.019(5) N1 0.056(6) 0.064(7) 0.057(7) 0.019(7) 0.004(6) -0.001(6) C11 0.054(2) 0.0156(13) 0.062(2) 0.002(2) 0.0093(18) 0.0018(19) C2 0.054(2) 0.0156(13) 0.062(2) 0.002(2) 0.0093(18) 0.0018(19) C6 0.060(6) 0.034(6) 0.059(8) 0.013(7) 0.019(6) -0.003(6) C1 0.072(9) 0.037(7) 0.032(6) 0.004(7) -0.007(7) 0.004(7) C3 0.053(7) 0.022(6) 0.058(8) 0.012(7) 0.008(7) -0.022(6) C18 0.061(8) 0.043(9) 0.068(10) -0.019(8) -0.015(8) 0.007(8) C13 0.068(8) 0.038(8) 0.053(9) 0.002(8) 0.009(6) 0.022(7) C16 0.034(6) 0.032(7) 0.076(9) -0.024(8) 0.006(6) 0.008(6) C17 0.046(7) 0.043(7) 0.072(9) 0.005(7) 0.001(7) 0.003(6) C14 0.083(9) 0.066(9) 0.047(8) -0.002(9) 0.002(7) 0.002(8) C9 0.054(2) 0.0156(13) 0.062(2) 0.002(2) 0.0093(18) 0.0018(19) C15 0.044(7) 0.039(8) 0.065(9) 0.016(7) -0.017(6) 0.022(6) C10 0.044(7) 0.026(6) 0.100(9) 0.023(8) 0.002(7) -0.006(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 Cl1 C15 1.721(9) . ? O2 C11 1.183(10) . ? F3 C18 1.308(11) . ? N2 C2 1.231(10) . ? N2 O1 1.415(10) . ? N3 C11 1.354(10) . ? N3 C2 1.419(10) . ? O1 N1 1.393(9) . ? F2 C18 1.307(12) . ? C8 C7 1.368(11) . ? C8 C9 1.368(12) . ? C8 C18 1.503(12) . ? C5 C6 1.352(11) . ? C5 C10 1.370(11) . ? C5 C11 1.496(12) . ? C7 C6 1.405(12) . ? F1 C18 1.353(11) . ? N1 C1 1.296(12) . ? C2 C1 1.429(11) . ? C1 C3 1.465(12) . ? C3 C13 1.397(11) . ? C3 C17 1.420(11) . ? C13 C14 1.363(12) . ? C16 C15 1.357(12) . ? C16 C17 1.382(10) . ? C14 C15 1.378(11) . ? C9 C10 1.373(13) . ? 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 N2 O1 106.3(7) . . ? C11 N3 C2 121.3(8) . . ? N1 O1 N2 107.3(7) . . ? C7 C8 C9 121.8(9) . . ? C7 C8 C18 118.4(11) . . ? C9 C8 C18 119.5(11) . . ? C6 C5 C10 120.6(10) . . ? C6 C5 C11 115.7(10) . . ? C10 C5 C11 123.7(10) . . ? C8 C7 C6 118.6(9) . . ? C1 N1 O1 107.6(9) . . ? O2 C11 N3 123.4(10) . . ? O2 C11 C5 121.2(10) . . ? N3 C11 C5 115.3(8) . . ? N2 C2 N3 120.2(9) . . ? N2 C2 C1 112.2(9) . . ? N3 C2 C1 127.2(10) . . ? C5 C6 C7 119.7(10) . . ? N1 C1 C2 106.2(10) . . ? N1 C1 C3 121.1(10) . . ? C2 C1 C3 132.2(11) . . ? C13 C3 C17 120.4(11) . . ? C13 C3 C1 122.2(11) . . ? C17 C3 C1 117.1(10) . . ? F2 C18 F3 108.2(11) . . ? F2 C18 F1 104.1(10) . . ? F3 C18 F1 103.9(10) . . ? F2 C18 C8 112.3(10) . . ? F3 C18 C8 114.6(9) . . ? F1 C18 C8 113.0(11) . . ? C14 C13 C3 119.6(10) . . ? C15 C16 C17 123.2(10) . . ? C16 C17 C3 116.5(11) . . ? C13 C14 C15 120.9(11) . . ? C8 C9 C10 118.5(10) . . ? C16 C15 C14 119.3(10) . . ? C16 C15 Cl1 120.4(10) . . ? C14 C15 Cl1 120.0(10) . . ? C5 C10 C9 120.8(10) . . ? # 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