# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal ChemComm _publ_section_title ; Room Temperature Palladium Catalysed Coupling of Acyl Chlorides with Terminal Alkynes ; _publ_contact_author_name 'Dr Russell J Cox' _publ_contact_author_address ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; _publ_contact_author_email r.j.cox@bristol.ac.uk loop_ _publ_author_name _publ_author_address 'Dr Russell J Cox' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'Dougal J Ritson' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'Thomas A Dane' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'John Berge' ; GlaxoSmithKline New Frontiers Science Park (North) 3rd Avenue Harlow Essex CM19 5AW UK ; 'Jonathan P. H. Charmant' ; Structural Chemistry Laboratory School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'Anob Kantacha' ; Structural Chemistry Laboratory School of Chemistry University of Bristol Bristol BS8 1TS UK ; data_14 _database_code_depnum_ccdc_archive 'CCDC 252032' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C15 H9 N O3' _chemical_formula_sum 'C15 H9 N O3' _chemical_formula_weight 251.23 _chemical_absolute_configuration unk 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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.6488(6) _cell_length_b 7.1371(6) _cell_length_c 10.9816(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.617(2) _cell_angle_gamma 90.00 _cell_volume 594.20(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2936 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 27.5 _exptl_crystal_description Monoclinic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method none _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3914 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0273 _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 -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2516 _reflns_number_gt 2386 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0520P)^2^+0.0396P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 2516 _refine_ls_number_parameters 172 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0811 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 C1 C 0.20093(16) 1.4311(2) 1.20358(12) 0.0289(3) Uani 1 1 d . . . H1A H 0.2366 1.5274 1.1525 0.035 Uiso 1 1 calc R . . C2 C 0.20007(19) 1.4631(2) 1.32837(13) 0.0373(3) Uani 1 1 d . . . H2A H 0.2361 1.5813 1.3627 0.045 Uiso 1 1 calc R . . C3 C 0.14681(19) 1.3229(3) 1.40280(13) 0.0400(4) Uani 1 1 d . . . H3A H 0.1474 1.3449 1.4882 0.048 Uiso 1 1 calc R . . C4 C 0.09276(18) 1.1511(2) 1.35298(13) 0.0389(4) Uani 1 1 d . . . H4A H 0.0550 1.0562 1.4043 0.047 Uiso 1 1 calc R . . C5 C 0.09325(17) 1.1163(2) 1.22892(13) 0.0322(3) Uani 1 1 d . . . H5A H 0.0560 0.9981 1.1951 0.039 Uiso 1 1 calc R . . C6 C 0.14903(15) 1.25654(19) 1.15368(11) 0.0263(3) Uani 1 1 d . . . C7 C 0.15838(16) 1.21887(18) 1.02639(12) 0.0285(3) Uani 1 1 d . . . C8 C 0.17158(17) 1.18300(18) 0.92134(12) 0.0294(3) Uani 1 1 d . . . C9 C 0.20059(16) 1.13376(19) 0.79678(11) 0.0268(3) Uani 1 1 d . . . C10 C 0.28066(16) 0.94587(18) 0.78006(11) 0.0243(3) Uani 1 1 d . . . C11 C 0.31446(17) 0.82039(19) 0.87778(11) 0.0265(3) Uani 1 1 d . . . H11A H 0.2852 0.8535 0.9564 0.032 Uiso 1 1 calc R . . C12 C 0.39057(16) 0.64759(18) 0.86078(11) 0.0269(3) Uani 1 1 d . . . H12A H 0.4147 0.5614 0.9268 0.032 Uiso 1 1 calc R . . C13 C 0.43026(16) 0.60475(18) 0.74453(11) 0.0251(3) Uani 1 1 d . . . C14 C 0.39779(16) 0.7259(2) 0.64510(12) 0.0279(3) Uani 1 1 d . . . H14A H 0.4263 0.6914 0.5665 0.033 Uiso 1 1 calc R . . C15 C 0.32279(17) 0.89800(19) 0.66364(11) 0.0277(3) Uani 1 1 d . . . H15A H 0.2998 0.9839 0.5974 0.033 Uiso 1 1 calc R . . N1 N 0.51392(14) 0.42297(17) 0.72589(10) 0.0298(3) Uani 1 1 d . . . O1 O 0.16344(13) 1.24304(15) 0.71154(9) 0.0346(2) Uani 1 1 d . . . O2 O 0.56315(14) 0.32713(14) 0.81696(9) 0.0376(3) Uani 1 1 d . . . O3 O 0.53135(15) 0.37730(16) 0.62038(9) 0.0418(3) Uani 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 C1 0.0272(6) 0.0281(7) 0.0309(7) -0.0006(5) 0.0022(5) 0.0000(5) C2 0.0328(7) 0.0412(9) 0.0365(8) -0.0113(6) -0.0011(5) 0.0036(6) C3 0.0342(7) 0.0595(10) 0.0264(7) -0.0010(6) 0.0042(5) 0.0107(7) C4 0.0317(7) 0.0495(9) 0.0368(7) 0.0150(7) 0.0094(6) 0.0040(6) C5 0.0279(6) 0.0274(7) 0.0412(8) 0.0038(6) 0.0046(5) -0.0003(5) C6 0.0221(6) 0.0288(7) 0.0278(6) 0.0003(5) 0.0029(5) 0.0027(5) C7 0.0271(6) 0.0239(6) 0.0343(7) -0.0015(5) 0.0026(5) 0.0009(5) C8 0.0319(6) 0.0242(6) 0.0318(7) -0.0023(5) 0.0035(5) 0.0026(5) C9 0.0264(6) 0.0262(6) 0.0275(6) -0.0006(5) 0.0022(4) -0.0038(5) C10 0.0237(5) 0.0245(6) 0.0245(6) -0.0015(5) 0.0021(4) -0.0034(5) C11 0.0294(6) 0.0287(7) 0.0217(6) -0.0025(5) 0.0037(4) -0.0007(5) C12 0.0294(6) 0.0261(7) 0.0246(6) 0.0020(5) 0.0022(5) -0.0005(5) C13 0.0223(5) 0.0244(6) 0.0282(6) -0.0029(5) 0.0021(4) -0.0022(5) C14 0.0304(6) 0.0309(7) 0.0226(6) -0.0026(5) 0.0047(5) -0.0017(5) C15 0.0310(6) 0.0291(7) 0.0229(6) 0.0026(5) 0.0028(4) -0.0004(5) N1 0.0283(5) 0.0278(6) 0.0331(6) -0.0045(5) 0.0041(4) -0.0005(5) O1 0.0418(5) 0.0290(5) 0.0328(5) 0.0039(4) 0.0041(4) 0.0039(4) O2 0.0435(5) 0.0306(6) 0.0372(5) 0.0023(4) -0.0004(4) 0.0084(5) O3 0.0542(6) 0.0384(6) 0.0343(5) -0.0108(4) 0.0109(4) 0.0053(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 C1 C2 1.3902(19) . ? C1 C6 1.3971(18) . ? C1 H1A 0.9500 . ? C2 C3 1.387(2) . ? C2 H2A 0.9500 . ? C3 C4 1.384(2) . ? C3 H3A 0.9500 . ? C4 C5 1.385(2) . ? C4 H4A 0.9500 . ? C5 C6 1.4001(18) . ? C5 H5A 0.9500 . ? C6 C7 1.4346(17) . ? C7 C8 1.1989(18) . ? C8 C9 1.4575(18) . ? C9 O1 1.2226(16) . ? C9 C10 1.4957(19) . ? C10 C11 1.3954(18) . ? C10 C15 1.4014(17) . ? C11 C12 1.3869(18) . ? C11 H11A 0.9500 . ? C12 C13 1.3850(17) . ? C12 H12A 0.9500 . ? C13 C14 1.3892(18) . ? C13 N1 1.4728(17) . ? C14 C15 1.382(2) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? N1 O3 1.2278(15) . ? N1 O2 1.2288(15) . ? 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 C1 C6 119.66(13) . . ? C2 C1 H1A 120.2 . . ? C6 C1 H1A 120.2 . . ? C3 C2 C1 120.18(14) . . ? C3 C2 H2A 119.9 . . ? C1 C2 H2A 119.9 . . ? C4 C3 C2 120.13(13) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C5 120.56(14) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C4 C5 C6 119.52(14) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C1 C6 C5 119.94(12) . . ? C1 C6 C7 120.06(12) . . ? C5 C6 C7 119.97(12) . . ? C8 C7 C6 177.50(13) . . ? C7 C8 C9 175.74(14) . . ? O1 C9 C8 121.06(13) . . ? O1 C9 C10 122.37(12) . . ? C8 C9 C10 116.57(11) . . ? C11 C10 C15 120.24(12) . . ? C11 C10 C9 121.20(11) . . ? C15 C10 C9 118.56(11) . . ? C12 C11 C10 120.36(11) . . ? C12 C11 H11A 119.8 . . ? C10 C11 H11A 119.8 . . ? C13 C12 C11 117.88(11) . . ? C13 C12 H12A 121.1 . . ? C11 C12 H12A 121.1 . . ? C12 C13 C14 123.29(12) . . ? C12 C13 N1 118.36(11) . . ? C14 C13 N1 118.35(11) . . ? C15 C14 C13 118.16(12) . . ? C15 C14 H14A 120.9 . . ? C13 C14 H14A 120.9 . . ? C14 C15 C10 120.08(12) . . ? C14 C15 H15A 120.0 . . ? C10 C15 H15A 120.0 . . ? O3 N1 O2 124.08(13) . . ? O3 N1 C13 117.94(11) . . ? O2 N1 C13 117.98(10) . . ? 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 C6 C1 C2 C3 -0.45(19) . . . . ? C1 C2 C3 C4 -0.6(2) . . . . ? C2 C3 C4 C5 0.8(2) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C2 C1 C6 C5 1.25(17) . . . . ? C2 C1 C6 C7 -176.69(12) . . . . ? C4 C5 C6 C1 -1.03(18) . . . . ? C4 C5 C6 C7 176.91(12) . . . . ? O1 C9 C10 C11 -177.08(12) . . . . ? C8 C9 C10 C11 4.10(16) . . . . ? O1 C9 C10 C15 3.39(17) . . . . ? C8 C9 C10 C15 -175.43(11) . . . . ? C15 C10 C11 C12 0.24(18) . . . . ? C9 C10 C11 C12 -179.29(11) . . . . ? C10 C11 C12 C13 -0.33(18) . . . . ? C11 C12 C13 C14 0.07(18) . . . . ? C11 C12 C13 N1 178.97(11) . . . . ? C12 C13 C14 C15 0.29(18) . . . . ? N1 C13 C14 C15 -178.61(10) . . . . ? C13 C14 C15 C10 -0.38(18) . . . . ? C11 C10 C15 C14 0.13(18) . . . . ? C9 C10 C15 C14 179.66(11) . . . . ? C12 C13 N1 O3 172.30(12) . . . . ? C14 C13 N1 O3 -8.75(17) . . . . ? C12 C13 N1 O2 -8.25(16) . . . . ? C14 C13 N1 O2 170.71(12) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.144 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.051