# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Collings, Jonathan C.' 'Parsons, Alexander C.' 'Porres, Laurent' 'Beeby, Andrew' 'Batsanov, Andrei S.' 'Howard, Judith A. K.' 'Lydon, Donocadh P.' 'Low, Paul J.' 'Fairlamb, Ian J. S.' 'Marder, Todd B.' _publ_contact_author_name 'Prof Todd Marder' _publ_contact_author_address ; Department of Chemistry University of Durham South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email TODD.MARDER@DURHAM.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Optical Propeties of Donor-Acceptor Phenylene-Ethynylene Systems Containing the 6-Methylpyran-2-one Group as an Acceptor ; #====================================================================== data_(2) _database_code_depnum_ccdc_archive 'CCDC 264993' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-phenylethynyl-6-methylpyran-2-one ; _chemical_name_common 4-phenylethynyl-6-methyl-\a-pyrone _chemical_melting_point 426-428 _chemical_formula_moiety 'C16 H15 N O2' _chemical_formula_sum 'C16 H15 N O2' _chemical_formula_weight 253.29 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.307(1) _cell_length_b 8.038(1) _cell_length_c 12.305(1) _cell_angle_alpha 96.35(1) _cell_angle_beta 101.85(1) _cell_angle_gamma 112.68(1) _cell_volume 638.04(13) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 909 _cell_measurement_theta_min 12.0 _cell_measurement_theta_max 30.5 _exptl_crystal_description block _exptl_crystal_colour 'light brown' _exptl_crystal_size_min 0.16 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.58 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (5 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.85 cm. ; _diffrn_ambient_temperature 120(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 'SMART 6K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 9055 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3708 _reflns_number_gt 2953 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SMART version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXTL version 6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL version 6.12 (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)' _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. ; _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^)+(0.0998P)^2^+0.0058P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3708 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1490 _refine_ls_wR_factor_gt 0.1383 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.006 _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 O1 O 0.22505(10) 1.01154(9) 0.25667(5) 0.02183(18) Uani 1 1 d . . . O2 O 0.27530(12) 0.81250(10) 0.13977(6) 0.0305(2) Uani 1 1 d . . . N N 0.26172(13) 0.27942(11) 0.96113(7) 0.0234(2) Uani 1 1 d . . . C1 C 0.25844(15) 0.85283(13) 0.23377(8) 0.0224(2) Uani 1 1 d . . . C2 C 0.27127(15) 0.75766(13) 0.32544(8) 0.0220(2) Uani 1 1 d . . . H2 H 0.2941(19) 0.6498(18) 0.3089(11) 0.030(3) Uiso 1 1 d . . . C3 C 0.25024(13) 0.81869(12) 0.42818(7) 0.0200(2) Uani 1 1 d . . . C4 C 0.21298(14) 0.98195(12) 0.44435(8) 0.0200(2) Uani 1 1 d . . . H4 H 0.199(2) 1.0240(18) 0.5196(11) 0.034(3) Uiso 1 1 d . . . C5 C 0.20260(14) 1.07192(13) 0.35909(7) 0.0202(2) Uani 1 1 d . . . C6 C 0.17210(17) 1.24449(14) 0.36156(9) 0.0266(2) Uani 1 1 d . . . H61 H 0.129(2) 1.2740(19) 0.4267(12) 0.038(3) Uiso 1 1 d . . . H62 H 0.073(2) 1.233(2) 0.2966(13) 0.051(4) Uiso 1 1 d . . . H63 H 0.304(3) 1.349(2) 0.3657(14) 0.055(4) Uiso 1 1 d . . . C7 C 0.26471(14) 0.72702(12) 0.51986(8) 0.0223(2) Uani 1 1 d . . . C8 C 0.27404(14) 0.65436(12) 0.60032(8) 0.0217(2) Uani 1 1 d . . . C9 C 0.27892(14) 0.56352(13) 0.69327(8) 0.0208(2) Uani 1 1 d . . . C10 C 0.30099(14) 0.39720(13) 0.68339(7) 0.0209(2) Uani 1 1 d . . . H10 H 0.327(2) 0.3456(18) 0.6133(12) 0.035(3) Uiso 1 1 d . . . C11 C 0.29473(15) 0.30233(12) 0.77096(8) 0.0210(2) Uani 1 1 d . . . H11 H 0.313(2) 0.1847(18) 0.7583(11) 0.036(3) Uiso 1 1 d . . . C12 C 0.26585(13) 0.37119(12) 0.87406(7) 0.0188(2) Uani 1 1 d . . . C13 C 0.24690(15) 0.54053(13) 0.88425(8) 0.0217(2) Uani 1 1 d . . . H13 H 0.235(2) 0.5928(18) 0.9578(11) 0.032(3) Uiso 1 1 d . . . C14 C 0.25453(15) 0.63345(13) 0.79639(8) 0.0222(2) Uani 1 1 d . . . H14 H 0.249(2) 0.753(2) 0.8088(12) 0.042(4) Uiso 1 1 d . . . C15 C 0.27212(17) 0.10198(14) 0.94673(9) 0.0267(2) Uani 1 1 d . . . H151 H 0.396(2) 0.1098(17) 0.9251(11) 0.033(3) Uiso 1 1 d . . . H152 H 0.155(2) 0.0132(19) 0.8900(12) 0.040(4) Uiso 1 1 d . . . H153 H 0.280(2) 0.067(2) 1.0212(14) 0.048(4) Uiso 1 1 d . . . C16 C 0.20937(16) 0.33955(15) 1.06150(8) 0.0264(2) Uani 1 1 d . . . H161 H 0.072(2) 0.3198(19) 1.0442(12) 0.039(3) Uiso 1 1 d . . . H162 H 0.296(2) 0.470(2) 1.0983(12) 0.040(4) Uiso 1 1 d . . . H163 H 0.240(2) 0.273(2) 1.1205(14) 0.052(4) 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 0.0293(4) 0.0244(3) 0.0174(3) 0.0080(3) 0.0081(3) 0.0152(3) O2 0.0453(5) 0.0364(4) 0.0216(4) 0.0105(3) 0.0157(3) 0.0249(4) N 0.0302(4) 0.0268(4) 0.0179(4) 0.0099(3) 0.0085(3) 0.0145(3) C1 0.0252(4) 0.0258(5) 0.0212(4) 0.0069(3) 0.0086(3) 0.0140(4) C2 0.0274(5) 0.0236(4) 0.0216(4) 0.0090(3) 0.0091(3) 0.0152(4) C3 0.0201(4) 0.0218(4) 0.0188(4) 0.0076(3) 0.0052(3) 0.0088(3) C4 0.0227(4) 0.0212(4) 0.0174(4) 0.0054(3) 0.0056(3) 0.0100(3) C5 0.0211(4) 0.0225(4) 0.0179(4) 0.0051(3) 0.0048(3) 0.0103(3) C6 0.0358(5) 0.0269(5) 0.0235(5) 0.0077(4) 0.0074(4) 0.0193(4) C7 0.0256(5) 0.0231(4) 0.0211(4) 0.0079(3) 0.0075(3) 0.0118(4) C8 0.0228(4) 0.0229(4) 0.0204(4) 0.0065(3) 0.0062(3) 0.0099(4) C9 0.0226(4) 0.0212(4) 0.0192(4) 0.0069(3) 0.0050(3) 0.0095(3) C10 0.0258(4) 0.0227(4) 0.0160(4) 0.0051(3) 0.0063(3) 0.0113(4) C11 0.0266(4) 0.0207(4) 0.0174(4) 0.0049(3) 0.0054(3) 0.0118(4) C12 0.0205(4) 0.0207(4) 0.0157(4) 0.0061(3) 0.0043(3) 0.0089(3) C13 0.0263(4) 0.0248(5) 0.0175(4) 0.0052(3) 0.0068(3) 0.0138(4) C14 0.0268(5) 0.0220(4) 0.0213(4) 0.0066(3) 0.0060(3) 0.0134(4) C15 0.0347(5) 0.0237(5) 0.0248(5) 0.0108(4) 0.0083(4) 0.0137(4) C16 0.0308(5) 0.0333(5) 0.0189(4) 0.0095(4) 0.0104(4) 0.0144(4) _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 C5 1.3644(11) . ? O1 C1 1.3983(11) . ? O2 C1 1.2101(12) . ? N C12 1.3652(11) . ? N C15 1.4508(13) . ? N C16 1.4525(13) . ? C1 C2 1.4384(13) . ? C2 C3 1.3651(13) . ? C2 H2 0.952(13) . ? C3 C7 1.4219(12) . ? C3 C4 1.4407(12) . ? C4 C5 1.3442(12) . ? C4 H4 0.989(13) . ? C5 C6 1.4855(13) . ? C6 H61 0.956(14) . ? C6 H62 0.934(17) . ? C6 H63 0.992(16) . ? C7 C8 1.2070(13) . ? C8 C9 1.4250(12) . ? C9 C10 1.4023(13) . ? C9 C14 1.4036(13) . ? C10 C11 1.3857(12) . ? C10 H10 1.002(14) . ? C11 C12 1.4160(13) . ? C11 H11 1.005(14) . ? C12 C13 1.4150(13) . ? C13 C14 1.3789(12) . ? C13 H13 0.991(13) . ? C14 H14 0.975(15) . ? C15 H151 0.975(14) . ? C15 H152 0.950(15) . ? C15 H153 0.986(16) . ? C16 H161 0.925(15) . ? C16 H162 0.983(15) . ? C16 H163 0.990(17) . ? 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 C5 O1 C1 122.33(7) . . ? C12 N C15 120.38(8) . . ? C12 N C16 120.63(8) . . ? C15 N C16 118.04(8) . . ? O2 C1 O1 116.41(8) . . ? O2 C1 C2 127.54(9) . . ? O1 C1 C2 116.04(8) . . ? C3 C2 C1 121.65(8) . . ? C3 C2 H2 123.0(8) . . ? C1 C2 H2 115.3(8) . . ? C2 C3 C7 122.22(8) . . ? C2 C3 C4 118.86(8) . . ? C7 C3 C4 118.93(8) . . ? C5 C4 C3 119.58(8) . . ? C5 C4 H4 123.0(8) . . ? C3 C4 H4 117.4(8) . . ? C4 C5 O1 121.53(8) . . ? C4 C5 C6 127.01(8) . . ? O1 C5 C6 111.45(8) . . ? C5 C6 H61 111.7(8) . . ? C5 C6 H62 110.5(9) . . ? H61 C6 H62 108.5(13) . . ? C5 C6 H63 109.4(10) . . ? H61 C6 H63 107.2(13) . . ? H62 C6 H63 109.5(13) . . ? C8 C7 C3 177.03(10) . . ? C7 C8 C9 178.11(10) . . ? C10 C9 C14 117.62(8) . . ? C10 C9 C8 120.99(8) . . ? C14 C9 C8 121.35(8) . . ? C11 C10 C9 121.57(8) . . ? C11 C10 H10 117.8(8) . . ? C9 C10 H10 120.6(8) . . ? C10 C11 C12 120.71(8) . . ? C10 C11 H11 117.3(7) . . ? C12 C11 H11 122.0(7) . . ? N C12 C13 121.48(8) . . ? N C12 C11 121.01(8) . . ? C13 C12 C11 117.49(8) . . ? C14 C13 C12 120.97(8) . . ? C14 C13 H13 121.2(8) . . ? C12 C13 H13 117.8(8) . . ? C13 C14 C9 121.61(9) . . ? C13 C14 H14 118.1(9) . . ? C9 C14 H14 120.2(9) . . ? N C15 H151 111.5(8) . . ? N C15 H152 110.4(9) . . ? H151 C15 H152 108.8(11) . . ? N C15 H153 106.9(9) . . ? H151 C15 H153 107.6(12) . . ? H152 C15 H153 111.7(12) . . ? N C16 H161 110.8(9) . . ? N C16 H162 113.5(8) . . ? H161 C16 H162 109.1(12) . . ? N C16 H163 108.7(9) . . ? H161 C16 H163 111.2(13) . . ? H162 C16 H163 103.3(12) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.344 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.068 #===========================================END