# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year 2011 _journal_volume 47 _journal_page_first 5043 _publ_contact_author_name 'Lourdes Infantes San Mateo' _publ_contact_author_email xlourdes@ctq.csic.es loop_ _publ_author_name D.Sucunza A.Samadi M.Chioua D.B.Silva C.Yunta L.Infantes M.C.Carreiras E.Soriano J.Marco-Contelles data_dsb48 _database_code_depnum_ccdc_archive 'CCDC 785405' #TrackingRef 'ccdc_dsb48_deposit.cif' _audit_creation_date 2010-07-22T18:35:54-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H7 Cl1 N4 O1' _chemical_formula_sum 'C11 H7 Cl1 N4 O1' _chemical_compound_source 'synthesis as described' _chemical_formula_weight 246.66 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.9010(4) _cell_length_b 8.9910(7) _cell_length_c 10.1390(8) _cell_angle_alpha 82.408(2) _cell_angle_beta 81.742(2) _cell_angle_gamma 82.153(2) _cell_volume 523.89(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4784 _cell_measurement_theta_min 4.44 _cell_measurement_theta_max 64.89 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.04 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 252 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5440 _exptl_absorpt_correction_T_max 0.7527 _exptl_absorpt_process_details SADABS-2008 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator 'Mirrors, multilayer' _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_unetI/netI 0.0312 _diffrn_reflns_number 5676 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.44 _diffrn_reflns_theta_max 65.97 _diffrn_reflns_theta_full 65.97 _diffrn_measured_fraction_theta_full 0.927 _diffrn_measured_fraction_theta_max 0.927 _reflns_number_total 1683 _reflns_number_gt 1543 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap #----------------------------------------------------------------------------# # 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^)+(0.1281P)^2^+0.7995P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _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 0.020(3) _refine_ls_number_reflns 1683 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1308 _refine_ls_wR_factor_gt 0.1284 _refine_ls_goodness_of_fit_ref 0.734 _refine_ls_restrained_S_all 0.734 _refine_ls_shift/su_max 0.043 _refine_ls_shift/su_mean 0.008 _refine_diff_density_max 0.337 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.125 #----------------------------------------------------------------------------# # 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' N N 0.0311 0.018 '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' Cl Cl 0.3639 0.7018 '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 C2 C 0.0004(5) -0.1629(3) 0.3706(3) 0.0271(6) Uani 1 1 d . . . C3 C 0.1381(4) -0.1219(2) 0.2373(2) 0.0217(5) Uani 1 1 d . . . C5 C 0.1208(4) -0.1820(3) 0.0042(2) 0.0234(6) Uani 1 1 d . . . C6 C -0.0002(4) -0.2671(3) -0.0690(2) 0.0241(6) Uani 1 1 d . . . C7 C -0.1824(4) -0.3406(3) -0.0065(3) 0.0251(6) Uani 1 1 d . . . C8 C -0.2546(4) -0.3448(3) 0.1316(2) 0.0233(5) Uani 1 1 d . . . C9 C -0.1320(4) -0.2710(3) 0.2074(2) 0.0221(5) Uani 1 1 d . . . C11 C -0.2942(5) -0.3488(3) 0.4443(3) 0.0303(6) Uani 1 1 d . . . C31 C 0.3129(4) -0.0399(3) 0.2124(2) 0.0237(6) Uani 1 1 d . . . C61 C 0.0759(4) -0.2682(3) -0.2092(3) 0.0268(6) Uani 1 1 d . . . C81 C -0.4546(4) -0.4144(3) 0.1884(2) 0.0252(6) Uani 1 1 d . . . N1 N -0.1527(3) -0.2633(2) 0.3383(2) 0.0241(5) Uani 1 1 d . . . N4 N 0.0413(3) -0.1895(2) 0.14199(19) 0.0217(5) Uani 1 1 d . . . N61 N 0.1397(4) -0.2728(3) -0.3217(2) 0.0332(6) Uani 1 1 d . . . N81 N -0.6206(4) -0.4692(2) 0.2278(2) 0.0310(5) Uani 1 1 d . . . O51 O 0.2773(3) -0.1080(2) -0.04401(17) 0.0303(5) Uani 1 1 d . . . Cl31 Cl 0.40086(10) 0.02877(6) 0.34609(5) 0.0287(3) Uani 1 1 d . . . H11A H -0.294(5) -0.447(4) 0.420(3) 0.030(7) Uiso 1 1 d . . . H2A H 0.095(4) -0.213(3) 0.435(3) 0.018(6) Uiso 1 1 d . . . H11B H -0.224(5) -0.356(3) 0.525(3) 0.029(7) Uiso 1 1 d . . . H2B H -0.088(5) -0.074(3) 0.401(3) 0.023(6) Uiso 1 1 d . . . H7 H -0.263(4) -0.390(3) -0.057(3) 0.016(6) Uiso 1 1 d . . . H31 H 0.398(5) -0.015(3) 0.125(3) 0.038(8) Uiso 1 1 d . . . H11C H -0.452(7) -0.301(4) 0.458(3) 0.053(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0270(13) 0.0340(14) 0.0233(13) -0.0078(11) -0.0038(11) -0.0098(11) C3 0.0253(12) 0.0219(11) 0.0190(12) -0.0056(9) -0.0051(9) -0.0016(9) C5 0.0261(13) 0.0227(12) 0.0217(12) -0.0040(9) -0.0048(10) -0.0010(10) C6 0.0252(12) 0.0241(12) 0.0239(13) -0.0056(10) -0.0055(10) -0.0014(10) C7 0.0262(13) 0.0231(12) 0.0284(13) -0.0081(10) -0.0097(10) 0.0004(10) C8 0.0222(12) 0.0228(12) 0.0258(13) -0.0048(9) -0.0045(10) -0.0025(9) C9 0.0204(12) 0.0200(11) 0.0257(13) -0.0030(9) -0.0028(9) -0.0016(9) C11 0.0352(15) 0.0345(15) 0.0224(14) -0.0029(11) 0.0012(11) -0.0144(12) C31 0.0256(12) 0.0241(12) 0.0228(13) -0.0068(10) -0.0043(10) -0.0024(10) C61 0.0275(13) 0.0247(12) 0.0295(15) -0.0055(10) -0.0087(11) -0.0003(10) C81 0.0265(14) 0.0240(12) 0.0267(13) -0.0063(10) -0.0071(10) -0.0011(10) N1 0.0244(11) 0.0278(10) 0.0213(11) -0.0047(8) -0.0004(8) -0.0088(8) N4 0.0213(10) 0.0242(10) 0.0213(10) -0.0047(8) -0.0054(8) -0.0038(8) N61 0.0370(13) 0.0388(13) 0.0252(13) -0.0077(9) -0.0059(10) -0.0029(10) N81 0.0275(12) 0.0312(11) 0.0369(13) -0.0066(9) -0.0063(9) -0.0073(9) O51 0.0315(10) 0.0386(10) 0.0230(10) -0.0057(7) 0.0007(7) -0.0143(8) Cl31 0.0276(4) 0.0355(4) 0.0267(4) -0.0108(3) -0.0042(3) -0.0098(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 C2 N1 1.458(3) . ? C2 C3 1.503(3) . ? C2 H2A 0.95(3) . ? C2 H2B 0.96(3) . ? C3 C31 1.325(4) . ? C3 N4 1.427(3) . ? C5 O51 1.219(3) . ? C5 N4 1.404(3) . ? C5 C6 1.449(3) . ? C6 C7 1.372(4) . ? C6 C61 1.429(3) . ? C7 C8 1.402(4) . ? C7 H7 0.94(3) . ? C8 C9 1.406(3) . ? C8 C81 1.424(3) . ? C9 N1 1.325(3) . ? C9 N4 1.380(3) . ? C11 N1 1.464(3) . ? C11 H11A 0.95(3) . ? C11 H11B 0.96(3) . ? C11 H11C 0.97(4) . ? C31 Cl31 1.731(2) . ? C31 H31 0.97(3) . ? C61 N61 1.153(3) . ? C81 N81 1.153(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 102.81(19) . . ? N1 C2 H2A 110.7(15) . . ? C3 C2 H2A 112.2(15) . . ? N1 C2 H2B 110.1(16) . . ? C3 C2 H2B 109.3(16) . . ? H2A C2 H2B 111(2) . . ? C31 C3 N4 126.8(2) . . ? C31 C3 C2 127.4(2) . . ? N4 C3 C2 105.76(19) . . ? O51 C5 N4 120.4(2) . . ? O51 C5 C6 125.7(2) . . ? N4 C5 C6 113.9(2) . . ? C7 C6 C61 121.8(2) . . ? C7 C6 C5 121.2(2) . . ? C61 C6 C5 117.0(2) . . ? C6 C7 C8 122.5(2) . . ? C6 C7 H7 119.6(16) . . ? C8 C7 H7 117.9(16) . . ? C9 C8 C7 117.8(2) . . ? C9 C8 C81 122.6(2) . . ? C7 C8 C81 119.5(2) . . ? N1 C9 N4 110.1(2) . . ? N1 C9 C8 130.9(2) . . ? N4 C9 C8 119.0(2) . . ? N1 C11 H11A 108.4(17) . . ? N1 C11 H11B 107.4(17) . . ? H11A C11 H11B 110(2) . . ? N1 C11 H11C 112(2) . . ? H11A C11 H11C 109(3) . . ? H11B C11 H11C 110(3) . . ? C3 C31 Cl31 118.13(19) . . ? C3 C31 H31 125.3(19) . . ? Cl31 C31 H31 116.5(19) . . ? N61 C61 C6 178.3(3) . . ? N81 C81 C8 176.3(3) . . ? C9 N1 C11 127.3(2) . . ? C9 N1 C2 111.52(19) . . ? C11 N1 C2 121.0(2) . . ? C9 N4 C5 125.4(2) . . ? C9 N4 C3 109.52(19) . . ? C5 N4 C3 124.99(19) . . ? 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 N1 C2 C3 C31 -175.4(2) . . . . ? N1 C2 C3 N4 4.8(2) . . . . ? O51 C5 C6 C7 -176.6(2) . . . . ? N4 C5 C6 C7 3.0(3) . . . . ? O51 C5 C6 C61 2.2(4) . . . . ? N4 C5 C6 C61 -178.24(19) . . . . ? C61 C6 C7 C8 177.9(2) . . . . ? C5 C6 C7 C8 -3.4(4) . . . . ? C6 C7 C8 C9 -0.5(3) . . . . ? C6 C7 C8 C81 175.8(2) . . . . ? C7 C8 C9 N1 -175.9(2) . . . . ? C81 C8 C9 N1 8.0(4) . . . . ? C7 C8 C9 N4 4.5(3) . . . . ? C81 C8 C9 N4 -171.6(2) . . . . ? N4 C3 C31 Cl31 -179.44(17) . . . . ? C2 C3 C31 Cl31 0.8(3) . . . . ? C7 C6 C61 N61 -74(9) . . . . ? C5 C6 C61 N61 107(9) . . . . ? C9 C8 C81 N81 151(4) . . . . ? C7 C8 C81 N81 -25(4) . . . . ? N4 C9 N1 C11 -171.5(2) . . . . ? C8 C9 N1 C11 8.9(4) . . . . ? N4 C9 N1 C2 4.3(3) . . . . ? C8 C9 N1 C2 -175.3(2) . . . . ? C3 C2 N1 C9 -5.6(3) . . . . ? C3 C2 N1 C11 170.5(2) . . . . ? N1 C9 N4 C5 175.2(2) . . . . ? C8 C9 N4 C5 -5.1(3) . . . . ? N1 C9 N4 C3 -0.9(3) . . . . ? C8 C9 N4 C3 178.7(2) . . . . ? O51 C5 N4 C9 -179.1(2) . . . . ? C6 C5 N4 C9 1.3(3) . . . . ? O51 C5 N4 C3 -3.5(3) . . . . ? C6 C5 N4 C3 176.9(2) . . . . ? C31 C3 N4 C9 177.6(2) . . . . ? C2 C3 N4 C9 -2.6(2) . . . . ? C31 C3 N4 C5 1.4(4) . . . . ? C2 C3 N4 C5 -178.8(2) . . . . ? # 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