Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'M. Bryce' _publ_contact_author_address ; Department of Chemistry University of Durham Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email M.R.BRYCE@DURHAM.AC.UK _publ_section_title ; Carbon-rich molecules: synthesis and isolation of aryl/heteroaryl terminal bis(butadiynes) (HC?C-C?C-Ar-C?C-C?CH) and their applications in the synthesis of oligo(arylenebutadiynylene) molecular wires ; loop_ _publ_author_name 'M. Bryce' 'A. Batsanov' 'Changsheng Wang' 'Kara West' data_4d _database_code_depnum_ccdc_archive 'CCDC 675274' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5-bis(buta-1,3-diynyl)-pyridine ; _chemical_name_common 2,5-bis(buta-1,3-diynyl)-pyridine _chemical_melting_point ? _chemical_formula_moiety 'C13 H5 N' _chemical_formula_sum 'C13 H5 N' _chemical_formula_weight 175.18 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.7926(8) _cell_length_b 20.217(4) _cell_length_c 12.385(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.91(1) _cell_angle_gamma 90.00 _cell_volume 946.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 408 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 22.7 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_twin_twinlaw_details '1 0 0 0 -1 0 -0.5 0 -1' _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 3 runs of narrow-frame \w-scans (scan width 0.3\% \w, 30s exposure), every run at a different \f angle. Crystal to detector distance 4.83 cm. Non-merohedral twin by twofold rotation around the [4 0 -1] axis, component contributions 0.650(4) and 0.350(4). ; _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 'Bruker SMART 6K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 5.6 _diffrn_standards_number 0 _diffrn_reflns_number 8467 _diffrn_reflns_av_R_equivalents 0.1512 _diffrn_reflns_av_sigmaI/netI 0.1255 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.14 _reflns_number_total 1685 _reflns_number_gt 683 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT version 6.02A (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. Without twinning correction: R1(gt)=0.172. ; _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^)+(0.1072P)^2^] 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_extinction_coef ? _refine_ls_number_reflns 1685 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1796 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.2080 _refine_ls_wR_factor_gt 0.1609 _refine_ls_goodness_of_fit_ref 0.865 _refine_ls_restrained_S_all 0.865 _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 N1 N 0.1952(12) 0.28856(19) 0.3529(3) 0.0416(11) Uani 1 1 d . . . C2 C 0.0662(13) 0.2846(2) 0.4520(4) 0.0382(13) Uani 1 1 d . . . C3 C 0.0128(14) 0.3396(2) 0.5141(4) 0.0424(14) Uani 1 1 d . . . H3 H -0.0734 0.3349 0.5835 0.051 Uiso 1 1 d R . . C4 C 0.0882(13) 0.4006(2) 0.4759(4) 0.0408(14) Uani 1 1 d . . . H4 H 0.0472 0.4388 0.5177 0.049 Uiso 1 1 d R . . C5 C 0.2179(14) 0.4069(2) 0.3765(4) 0.0363(13) Uani 1 1 d . . . C6 C 0.2618(14) 0.3491(3) 0.3167(4) 0.0431(14) Uani 1 1 d . . . H6 H 0.3426 0.3533 0.2465 0.052 Uiso 1 1 d R . . C7 C -0.0108(14) 0.2187(3) 0.4889(4) 0.0386(13) Uani 1 1 d . . . C8 C -0.0807(14) 0.1649(3) 0.5209(4) 0.0438(14) Uani 1 1 d . . . C9 C -0.1581(14) 0.1021(3) 0.5552(4) 0.0441(14) Uani 1 1 d . . . C10 C -0.2205(15) 0.0482(3) 0.5844(4) 0.0527(17) Uani 1 1 d . . . H10 H -0.2682 0.0048 0.6088 0.063 Uiso 1 1 d R . . C11 C 0.3037(14) 0.4702(3) 0.3345(4) 0.0395(13) Uani 1 1 d . . . C12 C 0.3785(15) 0.5237(3) 0.2995(4) 0.0368(13) Uani 1 1 d . . . C13 C 0.4683(14) 0.5844(3) 0.2597(4) 0.0417(14) Uani 1 1 d . . . C14 C 0.5503(16) 0.6373(3) 0.2263(4) 0.0551(17) Uani 1 1 d . . . H14 H 0.6140 0.6793 0.1997 0.066 Uiso 1 1 d 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 N1 0.049(3) 0.042(3) 0.034(2) -0.002(2) 0.004(2) -0.001(3) C2 0.037(3) 0.046(3) 0.031(3) -0.001(2) 0.000(3) -0.003(3) C3 0.043(3) 0.054(3) 0.030(3) -0.007(3) 0.000(3) 0.003(3) C4 0.047(4) 0.041(3) 0.035(3) -0.004(3) 0.006(3) 0.003(3) C5 0.041(4) 0.037(3) 0.031(3) -0.005(2) 0.003(2) 0.000(3) C6 0.045(4) 0.051(3) 0.034(3) -0.006(3) 0.003(3) -0.003(3) C7 0.037(3) 0.051(3) 0.027(3) -0.004(2) -0.002(2) -0.002(3) C8 0.041(3) 0.058(4) 0.033(3) 0.001(3) 0.003(3) -0.003(3) C9 0.043(3) 0.056(4) 0.033(3) 0.007(3) -0.001(3) -0.007(3) C10 0.061(4) 0.056(4) 0.042(3) 0.005(3) 0.009(3) -0.008(3) C11 0.035(3) 0.050(3) 0.032(3) -0.013(3) 0.000(3) 0.002(3) C12 0.043(3) 0.043(3) 0.024(2) -0.003(2) 0.004(2) 0.000(3) C13 0.039(3) 0.056(4) 0.031(3) -0.002(3) 0.004(3) 0.011(3) C14 0.056(4) 0.061(4) 0.048(3) 0.016(3) -0.001(3) -0.001(3) _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 N1 C6 1.335(6) . ? N1 C2 1.363(6) . ? C2 C3 1.377(6) . ? C2 C7 1.446(7) . ? C3 C4 1.359(6) . ? C3 H3 0.9502 . ? C4 C5 1.370(6) . ? C4 H4 0.9501 . ? C5 C6 1.401(6) . ? C5 C11 1.429(7) . ? C6 H6 0.9502 . ? C7 C8 1.196(7) . ? C8 C9 1.377(7) . ? C9 C10 1.179(7) . ? C10 H10 0.9500 . ? C11 C12 1.209(7) . ? C12 C13 1.376(8) . ? C13 C14 1.197(7) . ? C14 H14 0.9501 . ? 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 C6 N1 C2 116.7(4) . . ? N1 C2 C3 122.5(5) . . ? N1 C2 C7 115.9(4) . . ? C3 C2 C7 121.6(5) . . ? C4 C3 C2 119.6(5) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 119.9(5) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 117.8(5) . . ? C4 C5 C11 121.4(4) . . ? C6 C5 C11 120.8(5) . . ? N1 C6 C5 123.5(5) . . ? N1 C6 H6 118.3 . . ? C5 C6 H6 118.1 . . ? C8 C7 C2 178.4(6) . . ? C7 C8 C9 178.4(6) . . ? C10 C9 C8 179.3(7) . . ? C9 C10 H10 179.2 . . ? C12 C11 C5 179.5(6) . . ? C11 C12 C13 179.2(7) . . ? C14 C13 C12 179.0(7) . . ? C13 C14 H14 179.7 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C10 H10 C12 0.95 2.87 3.495(7) 124.1 4_466 C10 H10 C13 0.95 2.84 3.705(8) 151.9 4_466 C14 H14 N1 0.95 2.43 3.378(7) 175.0 2_655 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.320 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.068 #======================================END data_5a _database_code_depnum_ccdc_archive 'CCDC 675275' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-(4-buta-1,3-diynyl-2,5-dimethoxyphenyl)-2-methylhexa- 3,5-diyn-2-ol ; _chemical_name_common ;6-(4-buta-1,3-diynyl-2,5-dimethoxyphenyl)-2-methylhexa-3,5- diyn-2-ol ; _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 O3' _chemical_formula_sum 'C19 H16 O3' _chemical_formula_weight 292.32 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.555(2) _cell_length_b 9.126(1) _cell_length_c 19.831(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.46(1) _cell_angle_gamma 90.00 _cell_volume 3113.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2093 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 29.97 _exptl_crystal_description needle _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.084 _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 over a hemisphere of reciprocal space, by a combination of 2 runs of narrow-frame \w-scans (scan width 0.3\% \w, 60s exposure), every run at a different \f angle. Crystal to detector distance 4.84 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 'Bruker SMART 6K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 5.6 _diffrn_standards_number 0 _diffrn_reflns_number 11371 _diffrn_reflns_av_R_equivalents 0.0676 _diffrn_reflns_av_sigmaI/netI 0.0800 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3571 _reflns_number_gt 1987 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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^)+(0.0406P)^2^] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3571 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1036 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.0945 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 0.903 _refine_ls_restrained_S_all 0.903 _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 O1 O 0.54645(7) 0.12119(13) 0.66339(6) 0.0286(3) Uani 1 1 d . . . O2 O 0.56449(7) 0.72214(12) 0.69650(6) 0.0289(3) Uani 1 1 d . . . O3 O 0.29417(8) 0.96900(15) 0.35288(6) 0.0370(4) Uani 1 1 d . . . H0 H 0.3426(14) 0.960(3) 0.3433(13) 0.082(9) Uiso 1 1 d . . . C1 C 0.54961(10) 0.27113(18) 0.66831(9) 0.0231(4) Uani 1 1 d . . . C2 C 0.60210(10) 0.32724(19) 0.72527(8) 0.0229(4) Uani 1 1 d . . . C3 C 0.60872(10) 0.47853(19) 0.73555(9) 0.0233(4) Uani 1 1 d . . . H3 H 0.6435(9) 0.5166(19) 0.7734(8) 0.024(5) Uiso 1 1 d . . . C4 C 0.56421(10) 0.57336(18) 0.69006(9) 0.0235(4) Uani 1 1 d . . . C5 C 0.51356(9) 0.51782(19) 0.63158(8) 0.0218(4) Uani 1 1 d . . . C6 C 0.50663(10) 0.36596(19) 0.62143(9) 0.0233(4) Uani 1 1 d . . . H6 H 0.4719(9) 0.3333(17) 0.5810(8) 0.014(4) Uiso 1 1 d . . . C7 C 0.64883(10) 0.22746(19) 0.77142(8) 0.0245(4) Uani 1 1 d . . . C8 C 0.68722(10) 0.13751(19) 0.80756(9) 0.0251(4) Uani 1 1 d . . . C9 C 0.72902(10) 0.0301(2) 0.84769(9) 0.0278(4) Uani 1 1 d . . . C10 C 0.76438(13) -0.0650(2) 0.88060(10) 0.0385(5) Uani 1 1 d . . . H10 H 0.7914(13) -0.140(2) 0.9060(11) 0.065(7) Uiso 1 1 d . . . C11 C 0.46935(10) 0.61755(19) 0.58347(9) 0.0239(4) Uani 1 1 d . . . C12 C 0.43212(10) 0.70450(19) 0.54496(9) 0.0240(4) Uani 1 1 d . . . C13 C 0.38798(10) 0.80742(19) 0.50276(9) 0.0245(4) Uani 1 1 d . . . C14 C 0.35040(10) 0.8979(2) 0.46763(9) 0.0247(4) Uani 1 1 d . . . C15 C 0.30573(10) 1.0128(2) 0.42369(9) 0.0265(4) Uani 1 1 d . . . C16 C 0.22474(12) 1.0270(3) 0.43865(12) 0.0397(5) Uani 1 1 d . . . H161 H 0.1978(11) 0.930(2) 0.4277(9) 0.038(6) Uiso 1 1 d . . . H162 H 0.2288(11) 1.061(2) 0.4869(10) 0.043(6) Uiso 1 1 d . . . H163 H 0.1966(12) 1.103(2) 0.4076(11) 0.052(6) Uiso 1 1 d . . . C17 C 0.34988(13) 1.1577(2) 0.43529(12) 0.0361(5) Uani 1 1 d . . . H171 H 0.4001(12) 1.148(2) 0.4217(10) 0.046(6) Uiso 1 1 d . . . H172 H 0.3544(11) 1.189(2) 0.4852(11) 0.045(6) Uiso 1 1 d . . . H173 H 0.3228(11) 1.232(2) 0.4056(10) 0.045(6) Uiso 1 1 d . . . C18 C 0.48364(12) 0.0582(2) 0.61467(11) 0.0295(4) Uani 1 1 d . . . H181 H 0.4868(9) -0.053(2) 0.6243(8) 0.024(5) Uiso 1 1 d . . . H182 H 0.4325(11) 0.099(2) 0.6222(9) 0.035(5) Uiso 1 1 d . . . H183 H 0.4923(11) 0.077(2) 0.5659(10) 0.045(6) Uiso 1 1 d . . . C19 C 0.61525(13) 0.7831(2) 0.75556(10) 0.0327(5) Uani 1 1 d . . . H191 H 0.6707(11) 0.761(2) 0.7549(9) 0.032(5) Uiso 1 1 d . . . H192 H 0.6009(11) 0.743(2) 0.7996(10) 0.047(6) Uiso 1 1 d . . . H193 H 0.6048(10) 0.886(2) 0.7531(9) 0.036(5) 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 0.0340(7) 0.0172(6) 0.0299(7) -0.0012(5) -0.0052(6) -0.0008(5) O2 0.0385(7) 0.0168(6) 0.0279(7) -0.0015(5) -0.0022(6) -0.0025(6) O3 0.0384(8) 0.0451(9) 0.0248(7) 0.0006(6) -0.0005(6) 0.0083(7) C1 0.0264(9) 0.0168(8) 0.0252(9) -0.0010(8) 0.0032(8) 0.0008(8) C2 0.0253(9) 0.0225(9) 0.0207(9) 0.0020(7) 0.0039(8) 0.0017(7) C3 0.0270(9) 0.0229(10) 0.0180(9) -0.0007(8) -0.0005(8) -0.0023(8) C4 0.0268(9) 0.0189(9) 0.0249(9) -0.0007(7) 0.0055(8) -0.0019(8) C5 0.0227(9) 0.0210(9) 0.0213(9) 0.0019(7) 0.0031(7) 0.0006(7) C6 0.0239(9) 0.0233(10) 0.0205(9) -0.0017(8) -0.0008(8) -0.0009(8) C7 0.0297(10) 0.0203(9) 0.0223(9) -0.0039(8) 0.0019(8) -0.0042(8) C8 0.0281(9) 0.0212(10) 0.0240(9) -0.0030(8) 0.0008(8) -0.0024(8) C9 0.0304(10) 0.0275(10) 0.0233(9) -0.0014(8) -0.0004(8) 0.0007(8) C10 0.0476(13) 0.0316(12) 0.0320(11) 0.0036(10) -0.0025(10) 0.0078(10) C11 0.0260(9) 0.0203(9) 0.0239(9) -0.0014(8) 0.0015(8) -0.0031(8) C12 0.0258(9) 0.0206(9) 0.0238(9) -0.0017(8) 0.0005(8) -0.0048(8) C13 0.0267(9) 0.0205(9) 0.0245(9) -0.0025(8) 0.0011(8) -0.0044(8) C14 0.0252(9) 0.0232(10) 0.0238(9) -0.0002(8) 0.0005(8) -0.0042(8) C15 0.0275(9) 0.0268(10) 0.0231(9) 0.0048(8) 0.0000(8) 0.0028(8) C16 0.0316(11) 0.0506(15) 0.0361(12) 0.0140(11) 0.0050(10) 0.0081(11) C17 0.0369(12) 0.0238(11) 0.0440(13) 0.0063(10) -0.0010(11) 0.0026(9) C18 0.0293(10) 0.0216(10) 0.0348(11) -0.0052(9) -0.0008(9) -0.0047(8) C19 0.0400(12) 0.0210(10) 0.0326(11) -0.0051(9) -0.0033(10) -0.0061(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 O1 C1 1.372(2) . ? O1 C18 1.434(2) . ? O2 C4 1.364(2) . ? O2 C19 1.435(2) . ? O3 C15 1.435(2) . ? O3 H0 0.91(2) . ? C1 C6 1.380(2) . ? C1 C2 1.405(2) . ? C2 C3 1.397(2) . ? C2 C7 1.429(2) . ? C3 C4 1.376(2) . ? C3 H3 0.935(16) . ? C4 C5 1.408(2) . ? C5 C6 1.402(2) . ? C5 C11 1.431(2) . ? C6 H6 0.954(16) . ? C7 C8 1.204(2) . ? C8 C9 1.378(3) . ? C9 C10 1.185(3) . ? C10 H10 0.92(2) . ? C11 C12 1.201(2) . ? C12 C13 1.387(3) . ? C13 C14 1.191(2) . ? C14 C15 1.484(2) . ? C15 C16 1.515(3) . ? C15 C17 1.527(3) . ? C16 H161 1.003(19) . ? C16 H162 0.994(19) . ? C16 H163 0.99(2) . ? C17 H171 0.98(2) . ? C17 H172 1.02(2) . ? C17 H173 0.96(2) . ? C18 H181 1.031(18) . ? C18 H182 1.011(19) . ? C18 H183 1.02(2) . ? C19 H191 0.997(18) . ? C19 H192 1.02(2) . ? C19 H193 0.96(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 C1 O1 C18 117.54(14) . . ? C4 O2 C19 116.90(14) . . ? C15 O3 H0 105.9(16) . . ? O1 C1 C6 124.65(16) . . ? O1 C1 C2 115.56(14) . . ? C6 C1 C2 119.78(16) . . ? C3 C2 C1 119.98(15) . . ? C3 C2 C7 121.06(16) . . ? C1 C2 C7 118.95(16) . . ? C4 C3 C2 120.40(16) . . ? C4 C3 H3 119.2(11) . . ? C2 C3 H3 120.4(11) . . ? O2 C4 C3 125.02(16) . . ? O2 C4 C5 115.18(14) . . ? C3 C4 C5 119.80(16) . . ? C6 C5 C4 119.77(15) . . ? C6 C5 C11 120.87(16) . . ? C4 C5 C11 119.36(15) . . ? C1 C6 C5 120.20(16) . . ? C1 C6 H6 122.9(9) . . ? C5 C6 H6 116.9(9) . . ? C8 C7 C2 176.39(18) . . ? C7 C8 C9 177.62(19) . . ? C10 C9 C8 178.1(2) . . ? C9 C10 H10 179.2(15) . . ? C12 C11 C5 177.73(19) . . ? C11 C12 C13 177.6(2) . . ? C14 C13 C12 178.62(19) . . ? C13 C14 C15 178.30(19) . . ? O3 C15 C14 109.44(14) . . ? O3 C15 C16 105.05(15) . . ? C14 C15 C16 110.62(16) . . ? O3 C15 C17 110.95(16) . . ? C14 C15 C17 109.31(15) . . ? C16 C15 C17 111.40(18) . . ? C15 C16 H161 107.6(11) . . ? C15 C16 H162 108.9(11) . . ? H161 C16 H162 114.8(16) . . ? C15 C16 H163 108.0(12) . . ? H161 C16 H163 108.9(15) . . ? H162 C16 H163 108.4(16) . . ? C15 C17 H171 109.7(12) . . ? C15 C17 H172 109.2(11) . . ? H171 C17 H172 113.2(16) . . ? C15 C17 H173 110.0(12) . . ? H171 C17 H173 105.2(16) . . ? H172 C17 H173 109.5(16) . . ? O1 C18 H181 105.3(9) . . ? O1 C18 H182 109.8(10) . . ? H181 C18 H182 110.6(14) . . ? O1 C18 H183 109.2(11) . . ? H181 C18 H183 109.4(14) . . ? H182 C18 H183 112.4(15) . . ? O2 C19 H191 111.1(10) . . ? O2 C19 H192 109.8(11) . . ? H191 C19 H192 110.2(15) . . ? O2 C19 H193 105.0(11) . . ? H191 C19 H193 112.0(15) . . ? H192 C19 H193 108.6(16) . . ? 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 O1 C18 -13.3(3) . . . . ? C3 C4 O2 C19 -0.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H0 O1 0.91(2) 2.11(3) 2.9946(19) 163(2) 5_666 C10 H10 C13 0.92(2) 2.76(2) 3.658(3) 165.6(19) 8_556 C10 H10 C14 0.92(2) 2.76(2) 3.668(3) 169.1(19) 8_556 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.207 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.041 #===================================END data_5d _database_code_depnum_ccdc_archive 'CCDC 675276' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-(6-buta-1,3-diynyl-pyridin-3-yl)-2-methyl-hexa-3,5-diyn-2-ol ; _chemical_name_common 6-(6-buta-1,3-diynyl-pyridin-3-yl)-2-methyl-hexa-3,5-diyn-2-ol _chemical_melting_point ? _chemical_formula_moiety 'C16 H11 N O' _chemical_formula_sum 'C16 H11 N O' _chemical_formula_weight 233.26 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 _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7609(7) _cell_length_b 9.0756(10) _cell_length_c 12.6163(14) _cell_angle_alpha 87.79(1) _cell_angle_beta 77.87(1) _cell_angle_gamma 77.99(1) _cell_volume 630.77(12) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3932 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 29.95 _exptl_crystal_description blade _exptl_crystal_colour off-white _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7891 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker, 2003)' _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of narrow-frame \w-scans (scan width 0.3\% \w, 20s exposure), every run at a different \f angle. Crystal to detector distance 4.41 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 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 7737 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 29.97 _reflns_number_total 3464 _reflns_number_gt 2626 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.049 (Bruker, 1998)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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^)+(0.0554P)^2^+0.1233P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3464 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _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 O O 0.40890(16) 0.33716(9) 0.25495(7) 0.0258(2) Uani 1 1 d . . . H0 H 0.542(3) 0.271(2) 0.2769(14) 0.054(5) Uiso 1 1 d . . . N1 N 1.18119(18) 0.84130(11) 0.67156(8) 0.0250(2) Uani 1 1 d . . . C2 C 1.0411(2) 0.96719(13) 0.72327(9) 0.0227(2) Uani 1 1 d . . . C3 C 0.8176(2) 1.03413(13) 0.69904(10) 0.0261(3) Uani 1 1 d . . . H3 H 0.719(3) 1.1287(17) 0.7379(12) 0.035(4) Uiso 1 1 d . . . C4 C 0.7332(2) 0.96912(13) 0.62171(10) 0.0249(2) Uani 1 1 d . . . H4 H 0.581(3) 1.0131(17) 0.6040(12) 0.034(4) Uiso 1 1 d . . . C5 C 0.8736(2) 0.83775(12) 0.56937(9) 0.0210(2) Uani 1 1 d . . . C6 C 1.0976(2) 0.77951(13) 0.59696(9) 0.0239(2) Uani 1 1 d . . . H6 H 1.199(3) 0.6867(16) 0.5615(11) 0.030(4) Uiso 1 1 d . . . C7 C 1.1290(2) 1.02854(13) 0.80664(10) 0.0255(3) Uani 1 1 d . . . C8 C 1.1874(2) 1.08108(13) 0.88073(10) 0.0254(2) Uani 1 1 d . . . C9 C 1.2497(2) 1.13794(13) 0.96813(10) 0.0256(3) Uani 1 1 d . . . C10 C 1.3011(2) 1.18397(14) 1.04575(11) 0.0282(3) Uani 1 1 d . . . H10 H 1.338(3) 1.2192(18) 1.1076(13) 0.045(4) Uiso 1 1 d . . . C11 C 0.7895(2) 0.76129(13) 0.49287(9) 0.0229(2) Uani 1 1 d . . . C12 C 0.7139(2) 0.69436(13) 0.43106(9) 0.0232(2) Uani 1 1 d . . . C13 C 0.6278(2) 0.61860(13) 0.36029(9) 0.0231(2) Uani 1 1 d . . . C14 C 0.5565(2) 0.55154(13) 0.29743(9) 0.0225(2) Uani 1 1 d . . . C15 C 0.4828(2) 0.47274(13) 0.21312(9) 0.0217(2) Uani 1 1 d . . . C16 C 0.6975(2) 0.43614(15) 0.11757(10) 0.0283(3) Uani 1 1 d . . . H161 H 0.750(3) 0.5292(17) 0.0862(12) 0.032(4) Uiso 1 1 d . . . H162 H 0.649(3) 0.3812(18) 0.0612(13) 0.040(4) Uiso 1 1 d . . . H163 H 0.832(3) 0.3711(18) 0.1413(12) 0.038(4) Uiso 1 1 d . . . C17 C 0.2622(2) 0.57140(15) 0.17963(11) 0.0281(3) Uani 1 1 d . . . H171 H 0.206(3) 0.5153(17) 0.1250(12) 0.034(4) Uiso 1 1 d . . . H172 H 0.301(3) 0.6641(17) 0.1455(12) 0.032(4) Uiso 1 1 d . . . H173 H 0.128(3) 0.5960(17) 0.2430(13) 0.040(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 O 0.0304(5) 0.0266(4) 0.0252(4) 0.0019(3) -0.0107(3) -0.0122(4) N1 0.0269(5) 0.0254(5) 0.0253(5) -0.0030(4) -0.0104(4) -0.0055(4) C2 0.0272(6) 0.0226(5) 0.0216(5) -0.0012(4) -0.0086(4) -0.0090(4) C3 0.0289(6) 0.0216(5) 0.0294(6) -0.0051(5) -0.0096(5) -0.0038(5) C4 0.0250(6) 0.0235(6) 0.0287(6) -0.0013(5) -0.0111(5) -0.0049(5) C5 0.0264(6) 0.0217(5) 0.0183(5) -0.0001(4) -0.0077(4) -0.0093(4) C6 0.0262(6) 0.0230(5) 0.0239(5) -0.0037(4) -0.0083(4) -0.0047(4) C7 0.0268(6) 0.0235(6) 0.0284(6) -0.0027(5) -0.0086(5) -0.0066(5) C8 0.0262(6) 0.0231(5) 0.0289(6) -0.0031(5) -0.0094(5) -0.0055(4) C9 0.0263(6) 0.0221(5) 0.0300(6) -0.0037(5) -0.0092(5) -0.0044(4) C10 0.0325(7) 0.0253(6) 0.0303(6) -0.0048(5) -0.0129(5) -0.0063(5) C11 0.0244(6) 0.0240(5) 0.0220(5) 0.0000(4) -0.0078(4) -0.0058(4) C12 0.0235(6) 0.0237(6) 0.0230(5) -0.0017(4) -0.0070(4) -0.0039(4) C13 0.0241(6) 0.0236(5) 0.0225(5) -0.0022(4) -0.0068(4) -0.0043(4) C14 0.0228(5) 0.0240(5) 0.0215(5) -0.0025(4) -0.0061(4) -0.0048(4) C15 0.0244(6) 0.0234(5) 0.0201(5) -0.0025(4) -0.0075(4) -0.0076(4) C16 0.0301(6) 0.0309(6) 0.0241(6) -0.0048(5) -0.0025(5) -0.0088(5) C17 0.0295(6) 0.0302(6) 0.0273(6) -0.0038(5) -0.0129(5) -0.0046(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 O C15 1.4308(14) . ? O H0 0.952(19) . ? N1 C6 1.3325(14) . ? N1 C2 1.3546(15) . ? C2 C3 1.3947(17) . ? C2 C7 1.4349(15) . ? C3 C4 1.3783(16) . ? C3 H3 1.007(15) . ? C4 C5 1.3953(16) . ? C4 H4 0.954(15) . ? C5 C6 1.3987(16) . ? C5 C11 1.4268(15) . ? C6 H6 0.983(14) . ? C7 C8 1.2033(16) . ? C8 C9 1.3777(16) . ? C9 C10 1.1941(16) . ? C10 H10 0.934(17) . ? C11 C12 1.2069(15) . ? C12 C13 1.3753(15) . ? C13 C14 1.2026(15) . ? C14 C15 1.4825(15) . ? C15 C17 1.5225(17) . ? C15 C16 1.5254(17) . ? C16 H161 0.995(15) . ? C16 H162 1.000(16) . ? C16 H163 0.964(16) . ? C17 H171 1.015(15) . ? C17 H172 0.977(15) . ? C17 H173 0.985(16) . ? 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 C15 O H0 109.2(11) . . ? C6 N1 C2 118.03(10) . . ? N1 C2 C3 122.05(10) . . ? N1 C2 C7 117.32(10) . . ? C3 C2 C7 120.62(10) . . ? C4 C3 C2 119.34(11) . . ? C4 C3 H3 120.4(8) . . ? C2 C3 H3 120.3(8) . . ? C3 C4 C5 119.16(11) . . ? C3 C4 H4 120.6(9) . . ? C5 C4 H4 120.2(9) . . ? C4 C5 C6 117.88(10) . . ? C4 C5 C11 121.54(10) . . ? C6 C5 C11 120.54(10) . . ? N1 C6 C5 123.51(11) . . ? N1 C6 H6 117.2(8) . . ? C5 C6 H6 119.3(8) . . ? C8 C7 C2 175.65(13) . . ? C7 C8 C9 177.90(13) . . ? C10 C9 C8 178.07(13) . . ? C9 C10 H10 178.5(10) . . ? C12 C11 C5 177.78(12) . . ? C11 C12 C13 179.74(13) . . ? C14 C13 C12 178.89(13) . . ? C13 C14 C15 175.53(12) . . ? O C15 C14 110.86(9) . . ? O C15 C17 106.06(9) . . ? C14 C15 C17 109.54(9) . . ? O C15 C16 109.99(9) . . ? C14 C15 C16 108.51(9) . . ? C17 C15 C16 111.88(10) . . ? C15 C16 H161 111.4(8) . . ? C15 C16 H162 108.6(9) . . ? H161 C16 H162 110.1(12) . . ? C15 C16 H163 109.5(9) . . ? H161 C16 H163 109.0(12) . . ? H162 C16 H163 108.3(12) . . ? C15 C17 H171 109.6(8) . . ? C15 C17 H172 111.1(9) . . ? H171 C17 H172 107.7(11) . . ? C15 C17 H173 110.4(9) . . ? H171 C17 H173 108.1(12) . . ? H172 C17 H173 109.8(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O H0 N1 0.952(19) 1.929(19) 2.8761(14) 173.2(16) 2_766 C10 H10 O 0.934(17) 2.330(17) 3.2583(15) 172.8(14) 1_666 _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.303 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.041 #===================================END