# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Michael Greaney' 'Andrew J. Culshaw' 'Patrizia Mamone' 'Stephan A. Ohnmacht' _publ_contact_author_name 'Michael Greaney' _publ_contact_author_address ; School of Chemistry Joseph Black Building West Mains Road Edinburgh EH9 3JJ UNITED KINGDOM ; _publ_contact_author_email MICHAEL.GREANEY@ED.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Direct Arylations On Water: Synthesis of 2,5-Disubstituted Oxazoles Balsoxin and Texaline ; data_mg6003 _database_code_depnum_ccdc_archive 'CCDC 671459' _audit_creation_method SHELXL-97 _audit_creation_date 07-07-05 _chemical_compound_source 'S. Ohnmacht PM-034 ' _exptl_crystal_recrystallization_method ; >From dichloromethane ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N2 O' _chemical_formula_sum 'C15 H12 N2 O' _chemical_formula_weight 236.27 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 'Triclinic, twinned via 2[100]' _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.5552(3) _cell_length_b 11.7636(5) _cell_length_c 15.7218(7) _cell_angle_alpha 85.054(3) _cell_angle_beta 80.312(3) _cell_angle_gamma 81.946(3) _cell_volume 1180.83(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4521 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 30 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.720 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'Twinabs scaled by 0.98' _exptl_special_details ; The diffraction pattern was indexed with CELL_NOW. Data collection strategy optimised with COSMO. Oxford Crysosystems LT device. ; _diffrn_ambient_temperature 150(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 'Bruker Smart Apex CCD' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32765 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4968 _reflns_number_gt 4407 _reflns_threshold_expression >2sigma(I) _computing_data_collection Smart _computing_cell_refinement Saint _computing_data_reduction Saint _computing_structure_solution PLATON-FLIPPER _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF/PLATON _refine_special_details ; The crystal was non-merohedrally twinned, and the diffraction pattern was indexed on the basis of two orientation matrices related by the twin law [ 1.00025 0.00305 -0.00251] [ 0.50774 -0.99969 0.00099] [ 0.79609 -0.00175 -1.00036] which can be interpreted as a two-fold rotation about [100]. The twin scale factor refined to 0.3385(17). Both domains were integrated simultaneously, though only data based on the principal domain were used for refinement. Checkcif output: 761_ALERT_1_A CIF Contains no X-H Bonds ...................... ? 762_ALERT_1_A CIF Contains no X-Y-H or H-Y-H Angles .......... ? The H-atom parameters are idealised. 021_ALERT_1_B Ratio Unique / Expected Reflections too High ... 1.20 930_ALERT_2_B Check Twin Law ( 8 2 3)[ 1 0 0] Estimated BASF 0.27 Twinning is described above. 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.76 Multisca methods correct for all systematic errors that lead to disparities in the intensities of symmetry-equivalent data. These may include absorption by the mount, crystal decay, changes in the volume of the crystal illuminated, etc. Here twinning is an obvious source of further systematic errors. 063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.67 mm The ends of the crystals tended to fray on cutting. Gorbitz has shown that use of a large crystal does not appear to matter. See C. H. Gorbitz Acta Cryst. (1999). B55, 1090-1098 154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. 795_ALERT_4_C C-Atom in CIF Coordinate List out of Sequence .. C22 797_ALERT_4_C N-Atom in CIF Coordinate List out of Sequence .. N12 No action. 910_ALERT_3_C # Missing FCF Reflections Below Th(Min) ........ 1 911_ALERT_3_C # Missing FCF Refl Between THmin & STh/L= 0.595 3 #============================================================================== Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged) #============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------ 20.82 0.500 1.000 2481 2480 1 23.01 0.550 1.000 3286 3285 1 25.00 0.595 0.999 4147 4143 4 #----------------------------------------------------------- ACTA Min. Res. --- ; _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^)+(0.0416P)^2^+0.3925P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'charge flipping' _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom/difmap(methyl) _refine_ls_hydrogen_treatment 'riding/rotating group (Me)' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0090(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4968 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_restrained_S_all 1.169 _refine_ls_shift/su_max 0.002 _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 N11 N -0.1247(3) 0.43170(15) 0.37085(11) 0.0389(4) Uani 1 1 d . . . C21 C 0.0543(3) 0.45207(17) 0.38582(12) 0.0319(5) Uani 1 1 d . . . O31 O 0.1423(2) 0.37072(11) 0.44051(8) 0.0322(3) Uani 1 1 d . . . C41 C 0.0012(3) 0.29227(17) 0.46064(12) 0.0323(5) Uani 1 1 d . . . C51 C -0.1591(3) 0.32938(18) 0.41831(13) 0.0378(5) Uani 1 1 d . . . H51 H -0.2786 0.2912 0.4205 0.045 Uiso 1 1 calc R . . C61 C 0.1693(3) 0.54755(16) 0.35088(12) 0.0326(5) Uani 1 1 d . . . C71 C 0.0893(4) 0.62786(17) 0.29051(13) 0.0370(5) Uani 1 1 d . . . H71 H -0.0407 0.6209 0.2736 0.044 Uiso 1 1 calc R . . C81 C 0.1981(4) 0.71733(18) 0.25530(13) 0.0411(5) Uani 1 1 d . . . H81 H 0.1414 0.7716 0.2144 0.049 Uiso 1 1 calc R . . C91 C 0.3888(4) 0.72997(17) 0.27826(13) 0.0413(5) Uani 1 1 d . . . C101 C 0.4672(4) 0.64965(17) 0.33829(14) 0.0410(5) Uani 1 1 d . . . H101 H 0.5973 0.6566 0.3550 0.049 Uiso 1 1 calc R . . C111 C 0.3595(3) 0.55940(17) 0.37437(13) 0.0358(5) Uani 1 1 d . . . H111 H 0.4163 0.5054 0.4154 0.043 Uiso 1 1 calc R . . C121 C 0.5069(4) 0.82761(19) 0.23844(16) 0.0553(7) Uani 1 1 d . . . H12A H 0.5408 0.8217 0.1757 0.083 Uiso 1 1 calc R . . H12B H 0.6361 0.8235 0.2628 0.083 Uiso 1 1 calc R . . H12C H 0.4206 0.9011 0.2509 0.083 Uiso 1 1 calc R . . C131 C 0.0549(3) 0.19185(17) 0.51754(12) 0.0326(5) Uani 1 1 d . . . C141 C -0.1006(4) 0.12790(17) 0.55934(13) 0.0378(5) Uani 1 1 d . . . H141 H -0.2401 0.1542 0.5510 0.045 Uiso 1 1 calc R . . N151 N -0.0685(3) 0.03318(15) 0.60975(11) 0.0443(5) Uani 1 1 d . . . C161 C 0.1297(4) -0.00141(19) 0.62087(13) 0.0464(6) Uani 1 1 d . . . H161 H 0.1577 -0.0693 0.6565 0.056 Uiso 1 1 calc R . . C171 C 0.2949(4) 0.05606(19) 0.58343(14) 0.0464(6) Uani 1 1 d . . . H171 H 0.4326 0.0284 0.5935 0.056 Uiso 1 1 calc R . . C181 C 0.2569(4) 0.15438(19) 0.53110(13) 0.0403(5) Uani 1 1 d . . . H181 H 0.3681 0.1958 0.5047 0.048 Uiso 1 1 calc R . . N12 N 0.6519(3) 0.63678(14) 0.07667(12) 0.0393(4) Uani 1 1 d . . . C22 C 0.4644(3) 0.64023(16) 0.06039(12) 0.0306(4) Uani 1 1 d . . . O32 O 0.3682(2) 0.54777(11) 0.09571(8) 0.0310(3) Uani 1 1 d . . . C42 C 0.5114(3) 0.48165(16) 0.14001(12) 0.0318(5) Uani 1 1 d . . . C52 C 0.6826(3) 0.53583(18) 0.12749(14) 0.0393(5) Uani 1 1 d . . . H52 H 0.8070 0.5086 0.1503 0.047 Uiso 1 1 calc R . . C62 C 0.3472(3) 0.73024(16) 0.01236(12) 0.0310(4) Uani 1 1 d . . . C72 C 0.4360(3) 0.83011(17) -0.01910(13) 0.0365(5) Uani 1 1 d . . . H72 H 0.5703 0.8391 -0.0076 0.044 Uiso 1 1 calc R . . C82 C 0.3305(4) 0.91535(17) -0.06660(13) 0.0406(5) Uani 1 1 d . . . H82 H 0.3935 0.9824 -0.0875 0.049 Uiso 1 1 calc R . . C92 C 0.1344(3) 0.90542(17) -0.08456(12) 0.0368(5) Uani 1 1 d . . . C102 C 0.0458(3) 0.80656(17) -0.05221(12) 0.0364(5) Uani 1 1 d . . . H102 H -0.0892 0.7983 -0.0633 0.044 Uiso 1 1 calc R . . C112 C 0.1495(3) 0.72000(17) -0.00427(12) 0.0338(5) Uani 1 1 d . . . H112 H 0.0853 0.6535 0.0173 0.041 Uiso 1 1 calc R . . C122 C 0.0192(4) 0.99920(19) -0.13596(14) 0.0482(6) Uani 1 1 d . . . H12D H 0.0006 1.0712 -0.1068 0.072 Uiso 1 1 calc R . . H12E H -0.1177 0.9780 -0.1406 0.072 Uiso 1 1 calc R . . H12F H 0.0995 1.0096 -0.1939 0.072 Uiso 1 1 calc R . . C132 C 0.4489(3) 0.37713(16) 0.18837(12) 0.0299(4) Uani 1 1 d . . . C142 C 0.5773(4) 0.31548(19) 0.24247(14) 0.0419(5) Uani 1 1 d . . . H142 H 0.7055 0.3427 0.2455 0.050 Uiso 1 1 calc R . . N152 N 0.5324(3) 0.22050(16) 0.29048(12) 0.0469(5) Uani 1 1 d . . . C162 C 0.3512(4) 0.18412(18) 0.28588(13) 0.0417(5) Uani 1 1 d . . . H162 H 0.3161 0.1166 0.3196 0.050 Uiso 1 1 calc R . . C172 C 0.2125(3) 0.23961(17) 0.23458(13) 0.0380(5) Uani 1 1 d . . . H172 H 0.0846 0.2110 0.2333 0.046 Uiso 1 1 calc R . . C182 C 0.2621(3) 0.33729(17) 0.18509(13) 0.0350(5) Uani 1 1 d . . . H182 H 0.1688 0.3769 0.1491 0.042 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 N11 0.0326(10) 0.0402(10) 0.0434(10) 0.0008(8) -0.0072(8) -0.0037(8) C21 0.0289(11) 0.0351(11) 0.0302(10) -0.0034(8) -0.0047(9) 0.0021(9) O31 0.0300(8) 0.0332(7) 0.0337(7) -0.0007(6) -0.0059(6) -0.0048(6) C41 0.0314(11) 0.0371(11) 0.0285(10) -0.0054(8) 0.0001(9) -0.0084(9) C51 0.0298(11) 0.0434(12) 0.0407(11) -0.0011(9) -0.0039(9) -0.0089(9) C61 0.0335(11) 0.0306(10) 0.0315(10) -0.0068(8) 0.0003(9) -0.0003(9) C71 0.0388(12) 0.0361(11) 0.0350(11) -0.0047(9) -0.0062(9) 0.0010(9) C81 0.0548(15) 0.0321(11) 0.0335(11) -0.0013(9) -0.0056(10) 0.0021(10) C91 0.0517(14) 0.0309(11) 0.0381(11) -0.0104(9) 0.0043(10) -0.0035(10) C101 0.0388(13) 0.0367(12) 0.0473(12) -0.0080(10) -0.0030(10) -0.0052(10) C111 0.0360(12) 0.0318(11) 0.0382(11) -0.0028(9) -0.0056(9) 0.0003(9) C121 0.0755(19) 0.0391(13) 0.0508(14) -0.0047(11) 0.0012(13) -0.0176(12) C131 0.0363(12) 0.0356(11) 0.0269(10) -0.0066(8) -0.0034(9) -0.0076(9) C141 0.0417(13) 0.0350(11) 0.0353(11) -0.0079(9) 0.0005(9) -0.0050(10) N151 0.0577(13) 0.0366(10) 0.0367(10) -0.0055(8) 0.0026(9) -0.0094(9) C161 0.0701(19) 0.0373(12) 0.0307(11) -0.0024(9) -0.0061(11) -0.0057(12) C171 0.0536(15) 0.0481(14) 0.0394(12) 0.0013(10) -0.0171(11) -0.0032(11) C181 0.0398(13) 0.0461(13) 0.0374(11) 0.0015(9) -0.0099(10) -0.0113(10) N12 0.0314(10) 0.0340(10) 0.0529(11) -0.0044(8) -0.0046(8) -0.0066(8) C22 0.0275(11) 0.0285(10) 0.0361(10) -0.0066(8) 0.0018(9) -0.0096(8) O32 0.0296(8) 0.0300(7) 0.0335(7) -0.0026(6) -0.0043(6) -0.0049(6) C42 0.0320(11) 0.0327(10) 0.0315(10) -0.0078(8) -0.0067(8) -0.0007(9) C52 0.0289(11) 0.0376(12) 0.0533(13) -0.0053(10) -0.0132(10) -0.0012(9) C62 0.0293(11) 0.0303(10) 0.0317(10) -0.0072(8) 0.0030(8) -0.0045(8) C72 0.0324(12) 0.0354(11) 0.0419(11) -0.0047(9) -0.0007(9) -0.0101(9) C82 0.0472(14) 0.0308(11) 0.0418(12) 0.0004(9) 0.0033(10) -0.0122(10) C92 0.0455(14) 0.0341(11) 0.0275(10) -0.0042(8) 0.0013(9) -0.0008(10) C102 0.0341(12) 0.0400(12) 0.0351(11) -0.0039(9) -0.0046(9) -0.0050(9) C112 0.0335(12) 0.0332(11) 0.0336(10) -0.0026(8) 0.0014(9) -0.0089(9) C122 0.0635(16) 0.0423(13) 0.0375(12) 0.0007(10) -0.0079(11) -0.0042(12) C132 0.0298(11) 0.0308(10) 0.0286(10) -0.0085(8) -0.0028(8) -0.0004(8) C142 0.0401(13) 0.0457(13) 0.0419(12) 0.0020(10) -0.0118(10) -0.0084(10) N152 0.0493(12) 0.0462(11) 0.0468(11) 0.0068(9) -0.0171(9) -0.0062(9) C162 0.0514(15) 0.0367(12) 0.0357(11) 0.0007(9) -0.0032(10) -0.0074(11) C172 0.0376(12) 0.0372(12) 0.0403(11) -0.0064(9) -0.0057(10) -0.0066(10) C182 0.0328(12) 0.0341(11) 0.0388(11) -0.0032(9) -0.0088(9) -0.0025(9) _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 N11 C21 1.293(3) . ? N11 C51 1.386(3) . ? C21 O31 1.363(2) . ? C21 C61 1.457(3) . ? O31 C41 1.377(2) . ? C41 C51 1.340(3) . ? C41 C131 1.458(3) . ? C61 C111 1.387(3) . ? C61 C71 1.394(3) . ? C71 C81 1.379(3) . ? C81 C91 1.389(3) . ? C91 C101 1.386(3) . ? C91 C121 1.507(3) . ? C101 C111 1.385(3) . ? C131 C181 1.381(3) . ? C131 C141 1.393(3) . ? C141 N151 1.324(3) . ? N151 C161 1.342(3) . ? C161 C171 1.378(3) . ? C171 C181 1.379(3) . ? N12 C22 1.291(3) . ? N12 C52 1.383(3) . ? C22 O32 1.363(2) . ? C22 C62 1.453(3) . ? O32 C42 1.376(2) . ? C42 C52 1.345(3) . ? C42 C132 1.460(3) . ? C62 C112 1.388(3) . ? C62 C72 1.399(3) . ? C72 C82 1.375(3) . ? C82 C92 1.384(3) . ? C92 C102 1.392(3) . ? C92 C122 1.503(3) . ? C102 C112 1.383(3) . ? C132 C182 1.381(3) . ? C132 C142 1.386(3) . ? C142 N152 1.333(3) . ? N152 C162 1.333(3) . ? C162 C172 1.376(3) . ? C172 C182 1.377(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 C21 N11 C51 104.65(17) . . ? N11 C21 O31 113.53(17) . . ? N11 C21 C61 128.31(18) . . ? O31 C21 C61 118.15(17) . . ? C21 O31 C41 104.59(15) . . ? C51 C41 O31 107.35(17) . . ? C51 C41 C131 135.0(2) . . ? O31 C41 C131 117.62(18) . . ? C41 C51 N11 109.88(19) . . ? C111 C61 C71 118.81(19) . . ? C111 C61 C21 121.83(18) . . ? C71 C61 C21 119.34(19) . . ? C81 C71 C61 120.2(2) . . ? C71 C81 C91 121.5(2) . . ? C101 C91 C81 117.9(2) . . ? C101 C91 C121 121.3(2) . . ? C81 C91 C121 120.8(2) . . ? C111 C101 C91 121.3(2) . . ? C101 C111 C61 120.30(19) . . ? C181 C131 C141 117.34(19) . . ? C181 C131 C41 122.85(19) . . ? C141 C131 C41 119.79(19) . . ? N151 C141 C131 124.9(2) . . ? C141 N151 C161 116.2(2) . . ? N151 C161 C171 123.6(2) . . ? C161 C171 C181 118.9(2) . . ? C171 C181 C131 119.0(2) . . ? C22 N12 C52 104.23(17) . . ? N12 C22 O32 113.80(17) . . ? N12 C22 C62 128.07(18) . . ? O32 C22 C62 118.11(17) . . ? C22 O32 C42 104.77(15) . . ? C52 C42 O32 106.76(17) . . ? C52 C42 C132 135.59(19) . . ? O32 C42 C132 117.63(17) . . ? C42 C52 N12 110.42(19) . . ? C112 C62 C72 118.57(18) . . ? C112 C62 C22 122.00(17) . . ? C72 C62 C22 119.42(18) . . ? C82 C72 C62 120.6(2) . . ? C72 C82 C92 121.37(19) . . ? C82 C92 C102 117.82(19) . . ? C82 C92 C122 121.15(19) . . ? C102 C92 C122 121.0(2) . . ? C112 C102 C92 121.6(2) . . ? C102 C112 C62 120.05(18) . . ? C182 C132 C142 117.34(18) . . ? C182 C132 C42 122.99(18) . . ? C142 C132 C42 119.64(18) . . ? N152 C142 C132 124.2(2) . . ? C162 N152 C142 117.08(19) . . ? N152 C162 C172 123.2(2) . . ? C162 C172 C182 118.9(2) . . ? C172 C182 C132 119.31(19) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.204 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.051