# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Sean Kerwin' 'Wendi M. David' 'Cristina Gonzales' 'Christophe Laroche' 'Jing Li.' _publ_contact_author_name 'Sean Kerwin' _publ_contact_author_email SKERWIN@MAIL.UTEXAS.EDU _publ_section_title ; DFT and Experimental Studies of Cyclization Kinetics and Biological Evaluation of an Anticancer 1,2-Dialkynylimidazole ; # Attachment 'LAR1-final1.cif' data_lar1 _database_code_depnum_ccdc_archive 'CCDC 756647' #TrackingRef 'LAR1-final1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 N2 O' _chemical_formula_weight 222.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n 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 3.9680(4) _cell_length_b 10.7628(10) _cell_length_c 27.402(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.138(2) _cell_angle_gamma 90.00 _cell_volume 1170.02(18) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1825 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _exptl_crystal_description laths _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3467 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0845 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 25.21 _reflns_number_total 2039 _reflns_number_gt 969 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0053P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0092(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2039 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1410 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0765 _refine_ls_goodness_of_fit_ref 1.197 _refine_ls_restrained_S_all 1.197 _refine_ls_shift/su_max 0.042 _refine_ls_shift/su_mean 0.003 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 O1 O 0.2512(4) 0.27857(12) 0.12815(6) 0.0651(5) Uani 1 1 d . . . N1 N 0.7911(5) 0.31651(15) 0.44476(7) 0.0590(6) Uani 1 1 d . . . N2 N 0.9260(5) 0.11677(16) 0.44140(8) 0.0719(7) Uani 1 1 d . . . C1 C 0.8067(6) 0.21117(19) 0.41621(8) 0.0571(7) Uani 1 1 d . . . C2 C 0.9128(7) 0.2841(3) 0.49042(10) 0.0700(8) Uani 1 1 d . . . C3 C 0.9935(7) 0.1631(2) 0.48720(11) 0.0763(8) Uani 1 1 d . . . C4 C 0.7068(6) 0.21452(19) 0.36627(10) 0.0609(7) Uani 1 1 d . . . C5 C 0.6260(6) 0.22464(18) 0.32415(9) 0.0585(7) Uani 1 1 d . . . C6 C 0.5286(5) 0.23905(18) 0.27414(8) 0.0514(6) Uani 1 1 d . . . C7 C 0.3659(6) 0.3469(2) 0.25839(9) 0.0569(7) Uani 1 1 d . . . C8 C 0.2740(6) 0.36430(19) 0.21001(9) 0.0540(7) Uani 1 1 d . . . C9 C 0.3384(5) 0.27211(18) 0.17652(8) 0.0497(6) Uani 1 1 d . . . C10 C 0.5018(6) 0.1639(2) 0.19149(9) 0.0549(7) Uani 1 1 d . . . C11 C 0.5969(6) 0.14863(19) 0.23949(9) 0.0545(6) Uani 1 1 d . . . C12 C 0.0790(9) 0.3895(3) 0.11116(13) 0.0738(9) Uani 1 1 d . . . C13 C 0.6673(6) 0.4297(2) 0.43030(9) 0.0655(7) Uani 1 1 d . . . C14 C 0.5634(7) 0.5256(2) 0.41698(10) 0.0840(9) Uani 1 1 d . . . H2 H 0.929(6) 0.3409(19) 0.5178(10) 0.097(9) Uiso 1 1 d . . . H3 H 1.076(5) 0.1082(18) 0.5132(9) 0.080(7) Uiso 1 1 d . . . H7 H 0.320(5) 0.4107(15) 0.2828(8) 0.062(6) Uiso 1 1 d . . . H8 H 0.161(4) 0.4433(15) 0.2002(7) 0.058(6) Uiso 1 1 d . . . H10 H 0.536(5) 0.1031(15) 0.1682(8) 0.056(6) Uiso 1 1 d . . . H11 H 0.719(4) 0.0695(15) 0.2499(7) 0.056(6) Uiso 1 1 d . . . H12A H 0.029(6) 0.3710(19) 0.0779(10) 0.086(9) Uiso 1 1 d . . . H12B H 0.236(6) 0.4687(19) 0.1166(9) 0.110(9) Uiso 1 1 d . . . H12C H -0.130(7) 0.402(2) 0.1287(11) 0.119(13) Uiso 1 1 d . . . H14 H 0.477(6) 0.608(2) 0.4064(10) 0.113(9) 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 O1 0.0840(13) 0.0607(9) 0.0503(12) 0.0013(8) -0.0080(9) -0.0073(9) N1 0.0739(15) 0.0519(11) 0.0510(14) 0.0025(10) -0.0071(10) 0.0059(10) N2 0.0920(17) 0.0602(12) 0.0627(17) 0.0002(11) -0.0151(12) 0.0145(11) C1 0.0647(18) 0.0560(14) 0.0504(17) 0.0012(13) -0.0056(13) 0.0030(12) C2 0.088(2) 0.0708(18) 0.0508(19) -0.0002(15) -0.0170(14) 0.0039(15) C3 0.096(2) 0.0685(18) 0.064(2) 0.0101(15) -0.0183(16) 0.0123(16) C4 0.0681(19) 0.0585(14) 0.0558(19) -0.0004(13) -0.0045(14) 0.0057(12) C5 0.0618(18) 0.0588(14) 0.0548(19) -0.0002(13) -0.0013(14) 0.0010(12) C6 0.0538(16) 0.0518(14) 0.0484(16) -0.0003(11) -0.0026(12) -0.0043(11) C7 0.0689(18) 0.0492(14) 0.0525(18) -0.0081(13) 0.0012(13) 0.0009(12) C8 0.0638(18) 0.0455(13) 0.0525(18) 0.0016(13) -0.0028(13) 0.0004(12) C9 0.0583(16) 0.0516(13) 0.0392(16) 0.0010(11) -0.0008(11) -0.0108(12) C10 0.0685(18) 0.0444(14) 0.0521(19) -0.0069(12) 0.0047(14) -0.0025(12) C11 0.0614(17) 0.0475(14) 0.0545(18) 0.0011(12) 0.0010(13) 0.0021(12) C12 0.080(3) 0.078(2) 0.063(2) 0.0177(16) -0.014(2) -0.0059(18) C13 0.078(2) 0.0585(15) 0.0595(18) 0.0016(13) 0.0008(13) 0.0051(14) C14 0.108(2) 0.0667(17) 0.078(2) 0.0070(15) -0.0001(17) 0.0160(17) _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 O1 C9 1.365(2) . ? O1 C12 1.448(3) . ? N1 C13 1.369(3) . ? N1 C2 1.377(3) . ? N1 C1 1.380(3) . ? N2 C1 1.311(2) . ? N2 C3 1.372(3) . ? C1 C4 1.418(3) . ? C2 C3 1.344(3) . ? C2 H2 0.97(2) . ? C3 H3 0.98(2) . ? C4 C5 1.197(3) . ? C5 C6 1.425(3) . ? C6 C11 1.390(3) . ? C6 C7 1.392(3) . ? C7 C8 1.381(3) . ? C7 H7 0.978(19) . ? C8 C9 1.379(3) . ? C8 H8 0.996(16) . ? C9 C10 1.390(3) . ? C10 C11 1.371(3) . ? C10 H10 0.926(18) . ? C11 H11 1.019(16) . ? C12 H12A 0.95(3) . ? C12 H12B 1.06(2) . ? C12 H12C 0.98(3) . ? C13 C14 1.167(3) . ? C14 H14 0.99(2) . ? 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 C9 O1 C12 117.6(2) . . ? C13 N1 C2 127.3(2) . . ? C13 N1 C1 125.9(2) . . ? C2 N1 C1 106.73(18) . . ? C1 N2 C3 105.15(18) . . ? N2 C1 N1 111.0(2) . . ? N2 C1 C4 128.2(2) . . ? N1 C1 C4 120.8(2) . . ? C3 C2 N1 105.4(2) . . ? C3 C2 H2 130.6(14) . . ? N1 C2 H2 124.0(14) . . ? C2 C3 N2 111.7(2) . . ? C2 C3 H3 127.9(13) . . ? N2 C3 H3 120.2(12) . . ? C5 C4 C1 176.2(2) . . ? C4 C5 C6 179.0(2) . . ? C11 C6 C7 117.9(2) . . ? C11 C6 C5 121.9(2) . . ? C7 C6 C5 120.3(2) . . ? C8 C7 C6 121.5(2) . . ? C8 C7 H7 120.9(11) . . ? C6 C7 H7 117.6(11) . . ? C7 C8 C9 119.5(2) . . ? C7 C8 H8 118.9(11) . . ? C9 C8 H8 121.6(11) . . ? O1 C9 C8 124.26(19) . . ? O1 C9 C10 115.9(2) . . ? C8 C9 C10 119.8(2) . . ? C11 C10 C9 120.1(2) . . ? C11 C10 H10 122.3(12) . . ? C9 C10 H10 117.5(12) . . ? C10 C11 C6 121.1(2) . . ? C10 C11 H11 119.3(10) . . ? C6 C11 H11 119.5(10) . . ? O1 C12 H12A 103.0(13) . . ? O1 C12 H12B 110.1(11) . . ? H12A C12 H12B 114(2) . . ? O1 C12 H12C 110.7(15) . . ? H12A C12 H12C 110(2) . . ? H12B C12 H12C 109(2) . . ? C14 C13 N1 178.6(3) . . ? C13 C14 H14 178.6(15) . . ? 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 C3 N2 C1 N1 -0.9(3) . . . . ? C3 N2 C1 C4 178.0(3) . . . . ? C13 N1 C1 N2 -177.4(2) . . . . ? C2 N1 C1 N2 0.7(3) . . . . ? C13 N1 C1 C4 3.6(4) . . . . ? C2 N1 C1 C4 -178.3(2) . . . . ? C13 N1 C2 C3 177.9(2) . . . . ? C1 N1 C2 C3 -0.1(3) . . . . ? N1 C2 C3 N2 -0.4(3) . . . . ? C1 N2 C3 C2 0.8(3) . . . . ? N2 C1 C4 C5 -156(4) . . . . ? N1 C1 C4 C5 23(4) . . . . ? C1 C4 C5 C6 -21(18) . . . . ? C4 C5 C6 C11 165(15) . . . . ? C4 C5 C6 C7 -14(15) . . . . ? C11 C6 C7 C8 0.1(3) . . . . ? C5 C6 C7 C8 178.9(2) . . . . ? C6 C7 C8 C9 1.3(3) . . . . ? C12 O1 C9 C8 -0.2(3) . . . . ? C12 O1 C9 C10 179.7(2) . . . . ? C7 C8 C9 O1 178.4(2) . . . . ? C7 C8 C9 C10 -1.5(3) . . . . ? O1 C9 C10 C11 -179.5(2) . . . . ? C8 C9 C10 C11 0.4(3) . . . . ? C9 C10 C11 C6 1.0(4) . . . . ? C7 C6 C11 C10 -1.2(3) . . . . ? C5 C6 C11 C10 -180.0(2) . . . . ? C2 N1 C13 C14 157(11) . . . . ? C1 N1 C13 C14 -26(11) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.21 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.162 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.036