# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2011 data_block_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 #TrackingRef '- cif1-5.cif' _publ_contact_author_name 'Dr. Chmielewski, Marcin K.' _publ_contact_author_address ; Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12-14, 61-704 Pozna\'n, Poland ; _publ_contact_author_phone '+48 61 8528503 ext. 187' _publ_contact_author_fax '+48 61 8520532' _publ_contact_author_email maro@ibch.poznan.pl _publ_section_title ; Engineering N-(2-pyridyl)aminoethyl alkohols as potential precursors of thermolabile protection groups ; loop_ _publ_author_name _publ_author_footnote _publ_author_address M.K.Chmielewski . ; Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12-14, 61-704 Pozna\'n, Poland ; E.Tykarska . ; Department of Chemical Technology of Drugs, Poznan University of Medical Sciences Grunwaldzka 6 60-780 Pozna\'n Poland ; W.T.Markiewicz . ; Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12-14, 61-704 Pozna\'n, Poland ; W.Rypniewski . ; Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12-14, 61-704 Pozna\'n, Poland ; data_1 _database_code_depnum_ccdc_archive 'CCDC 827067' #TrackingRef 'cif1-5.cif' _audit_update_record ; 2011-02-07 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(2-pyridyl)N-benzylaminoethanol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H16 N2 O' _chemical_formula_sum 'C14 H16 N2 O' _chemical_formula_weight 228.29 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' 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 P2(1)/n _symmetry_space_group_name_HALL '-P 2yn' 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 10.756(2) _cell_length_b 5.9260(12) _cell_length_c 18.840(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.58(3) _cell_angle_gamma 90.00 _cell_volume 1184.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.81620 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2806 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 32.47 _reflns_number_total 2806 _reflns_number_gt 2732 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 for Windows - Version 2.00, Univ. of Glasgow 2008. Mercury CSD 2.3 - new features for the visualization and investigation of crystal structures, C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek and P. A. Wood, J. Appl. Cryst., 41, 466-470, 2008. ; _computing_publication_material 'Shelxl-97 (Sheldrick, 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. 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^)+(0.0698P)^2^+0.3233P] 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 2806 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 C2 C -0.02069(8) 0.42827(15) 0.22393(5) 0.0194(2) Uani 1 1 d . . . C3 C -0.09844(9) 0.24248(17) 0.23385(5) 0.0234(2) Uani 1 1 d . . . H3 H -0.1110 0.1265 0.2002 0.028 Uiso 1 1 calc R . . C4 C -0.15535(9) 0.23567(18) 0.29425(5) 0.0261(2) Uani 1 1 d . . . H4 H -0.2064 0.1142 0.3017 0.031 Uiso 1 1 calc R . . C5 C -0.13611(9) 0.41117(19) 0.34399(5) 0.0267(2) Uani 1 1 d . . . H5 H -0.1747 0.4113 0.3847 0.032 Uiso 1 1 calc R . . C6 C -0.05792(9) 0.58442(18) 0.33071(5) 0.0243(2) Uani 1 1 d . . . H6 H -0.0445 0.7017 0.3639 0.029 Uiso 1 1 calc R . . C7 C 0.12651(9) 0.62269(16) 0.15696(5) 0.0207(2) Uani 1 1 d . . . H7A H 0.1011 0.7600 0.1787 0.025 Uiso 1 1 calc R . . H7B H 0.1258 0.6527 0.1063 0.025 Uiso 1 1 calc R . . C8 C 0.25980(9) 0.56315(16) 0.19201(5) 0.0224(2) Uani 1 1 d . . . H8A H 0.3166 0.6859 0.1857 0.027 Uiso 1 1 calc R . . H8B H 0.2629 0.5387 0.2432 0.027 Uiso 1 1 calc R . . C9 C 0.01776(9) 0.26943(17) 0.10951(5) 0.0233(2) Uani 1 1 d . . . H9A H 0.0343 0.1248 0.1333 0.028 Uiso 1 1 calc R . . H9B H 0.0798 0.2901 0.0781 0.028 Uiso 1 1 calc R . . C10 C -0.11247(9) 0.26231(16) 0.06364(5) 0.0206(2) Uani 1 1 d . . . C11 C -0.15017(9) 0.06876(16) 0.02350(5) 0.0226(2) Uani 1 1 d . . . H11 H -0.0971 -0.0560 0.0272 0.027 Uiso 1 1 calc R . . C12 C -0.26621(10) 0.06010(18) -0.02196(5) 0.0261(2) Uani 1 1 d . . . H12 H -0.2895 -0.0686 -0.0492 0.031 Uiso 1 1 calc R . . C13 C -0.34695(10) 0.24404(19) -0.02656(6) 0.0279(2) Uani 1 1 d . . . H13 H -0.4248 0.2387 -0.0566 0.033 Uiso 1 1 calc R . . C14 C -0.31117(10) 0.43636(18) 0.01395(6) 0.0274(2) Uani 1 1 d . . . H14 H -0.3656 0.5592 0.0113 0.033 Uiso 1 1 calc R . . C15 C -0.19440(10) 0.44592(17) 0.05847(5) 0.0237(2) Uani 1 1 d . . . H15 H -0.1708 0.5759 0.0850 0.028 Uiso 1 1 calc R . . N1 N 0.00049(8) 0.59571(14) 0.27288(4) 0.02077(19) Uani 1 1 d . . . N2 N 0.03485(7) 0.44598(14) 0.16379(4) 0.0213(2) Uani 1 1 d . . . O1 O 0.29708(7) 0.36394(13) 0.15934(4) 0.02587(19) Uani 1 1 d . . . H1 H 0.3596 0.2988 0.1892 0.031 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 C2 0.0170(4) 0.0201(4) 0.0200(4) 0.0005(3) 0.0003(3) 0.0022(3) C3 0.0211(4) 0.0234(5) 0.0245(5) 0.0001(4) 0.0002(4) -0.0015(3) C4 0.0202(4) 0.0307(5) 0.0264(5) 0.0060(4) 0.0005(4) -0.0041(4) C5 0.0207(4) 0.0385(6) 0.0208(5) 0.0037(4) 0.0033(3) 0.0013(4) C6 0.0225(5) 0.0297(5) 0.0204(4) -0.0023(4) 0.0022(3) 0.0022(4) C7 0.0218(4) 0.0201(4) 0.0200(4) 0.0019(3) 0.0033(3) 0.0005(3) C8 0.0215(4) 0.0235(5) 0.0217(4) -0.0017(3) 0.0021(3) 0.0002(3) C9 0.0219(4) 0.0238(5) 0.0239(5) -0.0065(4) 0.0028(3) 0.0017(3) C10 0.0218(4) 0.0222(5) 0.0181(4) -0.0011(3) 0.0045(3) -0.0013(3) C11 0.0255(5) 0.0219(5) 0.0212(4) -0.0019(3) 0.0062(4) -0.0016(3) C12 0.0293(5) 0.0285(5) 0.0207(5) -0.0043(4) 0.0049(4) -0.0076(4) C13 0.0241(5) 0.0364(6) 0.0220(5) 0.0001(4) 0.0005(4) -0.0037(4) C14 0.0254(5) 0.0295(5) 0.0264(5) 0.0011(4) 0.0019(4) 0.0035(4) C15 0.0251(5) 0.0221(5) 0.0235(5) -0.0030(3) 0.0029(4) 0.0000(4) N1 0.0195(4) 0.0226(4) 0.0197(4) -0.0016(3) 0.0019(3) 0.0004(3) N2 0.0205(4) 0.0226(4) 0.0208(4) -0.0046(3) 0.0034(3) -0.0023(3) O1 0.0251(4) 0.0277(4) 0.0234(4) -0.0021(3) -0.0001(3) 0.0078(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 C2 N1 1.3479(12) . ? C2 N2 1.3701(13) . ? C2 C3 1.4137(13) . ? C3 C4 1.3795(14) . ? C3 H3 0.9300 . ? C4 C5 1.3921(15) . ? C4 H4 0.9300 . ? C5 C6 1.3763(15) . ? C5 H5 0.9300 . ? C6 N1 1.3469(13) . ? C6 H6 0.9300 . ? C7 N2 1.4586(12) . ? C7 C8 1.5168(13) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O1 1.4198(12) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.4531(12) . ? C9 C10 1.5191(14) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.3933(14) . ? C10 C11 1.3963(13) . ? C11 C12 1.3921(14) . ? C11 H11 0.9300 . ? C12 C13 1.3874(16) . ? C12 H12 0.9300 . ? C13 C14 1.3898(15) . ? C13 H13 0.9300 . ? C14 C15 1.3906(15) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O1 H1 0.8900 . ? 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 N1 C2 N2 117.52(8) . . ? N1 C2 C3 121.28(9) . . ? N2 C2 C3 121.19(9) . . ? C4 C3 C2 119.03(9) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 119.78(9) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 117.51(9) . . ? C6 C5 H5 121.2 . . ? C4 C5 H5 121.2 . . ? N1 C6 C5 124.44(10) . . ? N1 C6 H6 117.8 . . ? C5 C6 H6 117.8 . . ? N2 C7 C8 113.48(8) . . ? N2 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N2 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? O1 C8 C7 108.62(8) . . ? O1 C8 H8A 110.0 . . ? C7 C8 H8A 110.0 . . ? O1 C8 H8B 110.0 . . ? C7 C8 H8B 110.0 . . ? H8A C8 H8B 108.3 . . ? N2 C9 C10 114.64(8) . . ? N2 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? N2 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C15 C10 C11 118.71(9) . . ? C15 C10 C9 122.05(9) . . ? C11 C10 C9 119.21(9) . . ? C12 C11 C10 120.88(9) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C13 C12 C11 119.81(9) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 119.79(10) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C15 120.29(10) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C10 120.51(9) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? C6 N1 C2 117.93(9) . . ? C2 N2 C9 120.36(8) . . ? C2 N2 C7 121.47(8) . . ? C9 N2 C7 117.59(8) . . ? C8 O1 H1 108.9 . . ? 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 N1 C2 C3 C4 1.25(14) . . . . ? N2 C2 C3 C4 -178.04(8) . . . . ? C2 C3 C4 C5 0.36(15) . . . . ? C3 C4 C5 C6 -1.10(15) . . . . ? C4 C5 C6 N1 0.30(16) . . . . ? N2 C7 C8 O1 59.43(10) . . . . ? N2 C9 C10 C15 18.67(13) . . . . ? N2 C9 C10 C11 -163.42(8) . . . . ? C15 C10 C11 C12 1.25(14) . . . . ? C9 C10 C11 C12 -176.73(9) . . . . ? C10 C11 C12 C13 -1.32(15) . . . . ? C11 C12 C13 C14 0.37(15) . . . . ? C12 C13 C14 C15 0.63(16) . . . . ? C13 C14 C15 C10 -0.70(16) . . . . ? C11 C10 C15 C14 -0.24(15) . . . . ? C9 C10 C15 C14 177.68(9) . . . . ? C5 C6 N1 C2 1.26(15) . . . . ? N2 C2 N1 C6 177.30(8) . . . . ? C3 C2 N1 C6 -2.01(13) . . . . ? N1 C2 N2 C9 178.89(8) . . . . ? C3 C2 N2 C9 -1.79(13) . . . . ? N1 C2 N2 C7 7.89(13) . . . . ? C3 C2 N2 C7 -172.80(8) . . . . ? C10 C9 N2 C2 72.94(11) . . . . ? C10 C9 N2 C7 -115.71(9) . . . . ? C8 C7 N2 C2 84.48(11) . . . . ? C8 C7 N2 C9 -86.77(10) . . . . ? 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 O1 H1 N1 0.89 1.97 2.8236(12) 161.3 2_545 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 32.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.171 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.056 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 827068' #TrackingRef 'cif1-5.cif' _audit_update_record ; 2011-02-07 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(2-pyridyl)amino-1-ethanol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 N2 O' _chemical_formula_sum 'C7 H10 N2 O' _chemical_formula_weight 138.17 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 Orthorhombic _symmetry_space_group_name_H-M Pca2(1) _symmetry_space_group_name_HALL 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 8.8410(18) _cell_length_b 9.0530(18) _cell_length_c 8.6300(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 690.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 906 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 28.37 _reflns_number_total 906 _reflns_number_gt 885 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 for Windows - Version 2.00, Univ. of Glasgow 2008. Mercury CSD 2.3 - new features for the visualization and investigation of crystal structures, C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek and P. A. Wood, J. Appl. Cryst., 41, 466-470, 2008. ; _computing_publication_material 'Shelxl-97 (Sheldrick, 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. 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^)+(0.0915P)^2^+0.0752P] 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 SHELXL _refine_ls_extinction_coef 0.83(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.3(19) _refine_ls_number_reflns 906 _refine_ls_number_parameters 92 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1213 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.077 _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 C2 C 0.37179(19) -0.1637(2) 0.6782(2) 0.0304(4) Uani 1 1 d . . . C3 C 0.27769(19) -0.2336(2) 0.5684(2) 0.0342(5) Uani 1 1 d . . . H3 H 0.2032 -0.1804 0.5166 0.041 Uiso 1 1 calc R . . C4 C 0.2979(2) -0.3820(2) 0.5393(3) 0.0351(5) Uani 1 1 d . . . H4 H 0.2366 -0.4304 0.4680 0.042 Uiso 1 1 calc R . . C5 C 0.4114(2) -0.4590(2) 0.6179(2) 0.0359(5) Uani 1 1 d . . . H5 H 0.4281 -0.5589 0.5996 0.043 Uiso 1 1 calc R . . C6 C 0.4970(2) -0.3821(2) 0.7228(2) 0.0347(5) Uani 1 1 d . . . H6 H 0.5720 -0.4336 0.7758 0.042 Uiso 1 1 calc R . . C7 C 0.4383(2) 0.0671(2) 0.8189(2) 0.0319(4) Uani 1 1 d . . . H7A H 0.5350 0.0920 0.7728 0.038 Uiso 1 1 calc R . . H7B H 0.4570 0.0087 0.9112 0.038 Uiso 1 1 calc R . . C8 C 0.3546(2) 0.2072(2) 0.8622(2) 0.0322(5) Uani 1 1 d . . . H8A H 0.4220 0.2715 0.9197 0.039 Uiso 1 1 calc R . . H8B H 0.3248 0.2586 0.7683 0.039 Uiso 1 1 calc R . . N1 N 0.48038(17) -0.23668(18) 0.7549(2) 0.0319(4) Uani 1 1 d . . . H2 H 0.2986 0.0430 0.6271 0.038 Uiso 1 1 d R . . N2 N 0.34846(19) -0.01758(18) 0.70961(19) 0.0336(4) Uani 1 1 d . . . O1 O 0.22341(15) 0.17843(14) 0.95330(17) 0.0331(4) Uani 1 1 d . . . H1 H 0.1355 0.1832 0.8812 0.040 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 C2 0.0286(8) 0.0343(8) 0.0283(9) 0.0002(7) 0.0027(7) 0.0007(6) C3 0.0308(10) 0.0414(9) 0.0303(9) -0.0025(8) -0.0017(8) 0.0018(6) C4 0.0338(9) 0.0396(9) 0.0318(10) -0.0052(8) 0.0012(7) -0.0049(7) C5 0.0386(10) 0.0338(8) 0.0354(11) 0.0005(7) 0.0045(8) -0.0026(7) C6 0.0374(9) 0.0342(8) 0.0324(11) 0.0026(7) 0.0012(7) 0.0017(7) C7 0.0276(8) 0.0353(8) 0.0328(9) -0.0007(7) -0.0021(7) -0.0001(6) C8 0.0307(9) 0.0322(8) 0.0337(9) 0.0007(7) 0.0001(7) -0.0033(6) N1 0.0313(7) 0.0351(8) 0.0294(8) 0.0009(6) 0.0006(7) 0.0011(6) N2 0.0369(8) 0.0343(8) 0.0296(8) -0.0025(7) -0.0036(6) 0.0030(6) O1 0.0311(8) 0.0394(7) 0.0288(7) 0.0022(6) 0.0010(5) 0.0011(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 C2 N1 1.340(2) . ? C2 N2 1.366(2) . ? C2 C3 1.411(3) . ? C3 C4 1.378(3) . ? C3 H3 0.9300 . ? C4 C5 1.397(3) . ? C4 H4 0.9300 . ? C5 C6 1.371(3) . ? C5 H5 0.9300 . ? C6 N1 1.353(3) . ? C6 H6 0.9300 . ? C7 N2 1.452(2) . ? C7 C8 1.515(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O1 1.425(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? N2 H2 1.0015 . ? O1 H1 0.9967 . ? 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 N1 C2 N2 119.19(17) . . ? N1 C2 C3 122.18(16) . . ? N2 C2 C3 118.61(17) . . ? C4 C3 C2 118.91(17) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 119.40(19) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 117.65(18) . . ? C6 C5 H5 121.2 . . ? C4 C5 H5 121.2 . . ? N1 C6 C5 124.69(19) . . ? N1 C6 H6 117.7 . . ? C5 C6 H6 117.7 . . ? N2 C7 C8 109.57(15) . . ? N2 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N2 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? O1 C8 C7 112.34(15) . . ? O1 C8 H8A 109.1 . . ? C7 C8 H8A 109.1 . . ? O1 C8 H8B 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? C2 N1 C6 117.17(17) . . ? C2 N2 C7 123.91(16) . . ? C2 N2 H2 117.1 . . ? C7 N2 H2 114.4 . . ? C8 O1 H1 106.4 . . ? 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 N1 C2 C3 C4 0.1(3) . . . . ? N2 C2 C3 C4 -178.24(18) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C4 C5 C6 N1 -0.5(3) . . . . ? N2 C7 C8 O1 69.1(2) . . . . ? N2 C2 N1 C6 178.41(18) . . . . ? C3 C2 N1 C6 0.1(3) . . . . ? C5 C6 N1 C2 0.2(3) . . . . ? N1 C2 N2 C7 2.1(3) . . . . ? C3 C2 N2 C7 -179.44(18) . . . . ? C8 C7 N2 C2 -162.65(18) . . . . ? 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 N2 H2 O1 1.00 1.95 2.906(2) 159.6 4_554 O1 H1 N1 1.00 1.82 2.798(2) 167.0 3_455 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.230 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.043 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 827069' #TrackingRef 'cif1-5.cif' _audit_update_record ; 2011-02-07 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _publ_section_exptl_refinement ; in the absence of significant anomalus scattering effects Friedel pairs have been merged ; _chemical_name_systematic ; N-(2-pyridyl)amino-1-phenyloethanol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N2 O' _chemical_formula_sum 'C13 H14 N2 O' _chemical_formula_weight 214.26 _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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_HALL 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.0480(12) _cell_length_b 7.3150(15) _cell_length_c 24.334(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1076.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.81620 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1572 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 32.99 _reflns_number_total 1572 _reflns_number_gt 1527 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 for Windows - Version 2.00, Univ. of Glasgow 2008. Mercury CSD 2.3 - new features for the visualization and investigation of crystal structures, C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek and P. A. Wood, J. Appl. Cryst., 41, 466-470, 2008. ; _computing_publication_material 'Shelxl-97 (Sheldrick, 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. 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^)+(0.0837P)^2^+0.2059P] 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 SHELXL _refine_ls_extinction_coef 0.136(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(2) _refine_ls_number_reflns 1572 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1238 _refine_ls_wR_factor_gt 0.1229 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 C2 C -0.2796(3) -0.1304(3) -0.28045(7) 0.0284(4) Uani 1 1 d . . . C3 C -0.4383(3) -0.1914(3) -0.24214(8) 0.0311(4) Uani 1 1 d . . . H3 H -0.5736 -0.2379 -0.2537 0.037 Uiso 1 1 calc R . . C4 C -0.3873(3) -0.1802(3) -0.18700(8) 0.0332(4) Uani 1 1 d . . . H4 H -0.4880 -0.2206 -0.1608 0.040 Uiso 1 1 calc R . . C5 C -0.1844(3) -0.1082(3) -0.17071(7) 0.0338(4) Uani 1 1 d . . . H5 H -0.1489 -0.0969 -0.1337 0.041 Uiso 1 1 calc R . . C6 C -0.0382(3) -0.0542(3) -0.21074(7) 0.0322(4) Uani 1 1 d . . . H6 H 0.0980 -0.0075 -0.1999 0.039 Uiso 1 1 calc R . . C7 C -0.1970(3) -0.0412(3) -0.37645(7) 0.0299(4) Uani 1 1 d . . . H7A H -0.1639 0.0792 -0.3619 0.036 Uiso 1 1 calc R . . H7B H -0.2882 -0.0245 -0.4089 0.036 Uiso 1 1 calc R . . C8 C 0.0213(3) -0.1321(3) -0.39397(7) 0.0272(4) Uani 1 1 d . . . H8 H -0.0044 -0.2640 -0.3971 0.033 Uiso 1 1 calc R . . C9 C 0.0920(3) -0.0612(2) -0.44986(7) 0.0266(4) Uani 1 1 d . . . C10 C -0.0315(3) -0.1114(2) -0.49584(7) 0.0279(4) Uani 1 1 d . . . H10 H -0.1560 -0.1846 -0.4915 0.034 Uiso 1 1 calc R . . C11 C 0.0291(3) -0.0535(3) -0.54804(7) 0.0300(4) Uani 1 1 d . . . H11 H -0.0547 -0.0874 -0.5784 0.036 Uiso 1 1 calc R . . C12 C 0.2159(3) 0.0558(3) -0.55473(7) 0.0315(4) Uani 1 1 d . . . H12 H 0.2584 0.0937 -0.5896 0.038 Uiso 1 1 calc R . . C13 C 0.3385(3) 0.1078(2) -0.50903(7) 0.0302(4) Uani 1 1 d . . . H13 H 0.4626 0.1814 -0.5134 0.036 Uiso 1 1 calc R . . C14 C 0.2766(3) 0.0502(2) -0.45669(7) 0.0281(4) Uani 1 1 d . . . H14 H 0.3587 0.0863 -0.4262 0.034 Uiso 1 1 calc R . . N1 N -0.0820(3) -0.0655(2) -0.26512(6) 0.0302(4) Uani 1 1 d . . . N2 N -0.3242(3) -0.1412(2) -0.33569(6) 0.0319(4) Uani 1 1 d . . . H2 H -0.4874 -0.1585 -0.3437 0.038 Uiso 1 1 d R . . O1 O 0.1922(2) -0.1038(2) -0.35471(5) 0.0317(3) Uani 1 1 d . . . H1 H 0.1100 -0.0815 -0.3181 0.038 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 C2 0.0245(8) 0.0328(8) 0.0280(8) 0.0000(7) -0.0001(7) 0.0024(8) C3 0.0259(9) 0.0365(9) 0.0309(8) 0.0009(7) 0.0006(7) -0.0011(7) C4 0.0309(9) 0.0391(9) 0.0297(8) 0.0033(8) 0.0047(7) 0.0012(8) C5 0.0331(10) 0.0409(9) 0.0275(8) -0.0008(7) 0.0010(7) 0.0006(9) C6 0.0286(9) 0.0385(9) 0.0294(8) -0.0017(7) -0.0020(7) -0.0015(8) C7 0.0229(8) 0.0394(9) 0.0274(7) 0.0026(7) 0.0004(6) 0.0024(8) C8 0.0219(8) 0.0335(8) 0.0261(7) 0.0004(7) -0.0015(6) 0.0008(7) C9 0.0234(8) 0.0288(8) 0.0277(7) -0.0006(7) 0.0009(6) 0.0030(7) C10 0.0232(8) 0.0299(8) 0.0308(8) -0.0005(7) 0.0003(7) -0.0005(7) C11 0.0286(9) 0.0334(8) 0.0280(8) -0.0007(7) -0.0018(7) 0.0024(8) C12 0.0320(9) 0.0335(8) 0.0292(7) 0.0045(7) 0.0052(7) 0.0025(8) C13 0.0243(9) 0.0294(8) 0.0368(9) 0.0015(7) 0.0031(7) -0.0009(7) C14 0.0234(8) 0.0298(7) 0.0312(8) -0.0017(7) -0.0013(7) 0.0017(8) N1 0.0262(8) 0.0369(8) 0.0275(7) -0.0004(6) 0.0006(6) -0.0013(7) N2 0.0237(8) 0.0458(9) 0.0262(7) 0.0005(6) -0.0003(5) -0.0026(7) O1 0.0234(6) 0.0451(7) 0.0265(6) 0.0010(5) -0.0021(5) 0.0019(6) _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 C2 N1 1.339(2) . ? C2 N2 1.373(2) . ? C2 C3 1.410(3) . ? C3 C4 1.379(2) . ? C3 H3 0.9300 . ? C4 C5 1.393(3) . ? C4 H4 0.9300 . ? C5 C6 1.374(3) . ? C5 H5 0.9300 . ? C6 N1 1.352(2) . ? C6 H6 0.9300 . ? C7 N2 1.453(2) . ? C7 C8 1.539(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O1 1.423(2) . ? C8 C9 1.517(2) . ? C8 H8 0.9800 . ? C9 C14 1.392(3) . ? C9 C10 1.394(2) . ? C10 C11 1.388(2) . ? C10 H10 0.9300 . ? C11 C12 1.393(3) . ? C11 H11 0.9300 . ? C12 C13 1.390(3) . ? C12 H12 0.9300 . ? C13 C14 1.393(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? N2 H2 1.0137 . ? O1 H1 1.0332 . ? 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 N1 C2 N2 117.93(16) . . ? N1 C2 C3 122.37(16) . . ? N2 C2 C3 119.68(17) . . ? C4 C3 C2 118.16(18) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C3 C4 C5 119.76(17) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 118.30(17) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? N1 C6 C5 123.38(19) . . ? N1 C6 H6 118.3 . . ? C5 C6 H6 118.3 . . ? N2 C7 C8 115.19(16) . . ? N2 C7 H7A 108.5 . . ? C8 C7 H7A 108.5 . . ? N2 C7 H7B 108.5 . . ? C8 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? O1 C8 C9 110.34(14) . . ? O1 C8 C7 111.99(14) . . ? C9 C8 C7 110.01(14) . . ? O1 C8 H8 108.1 . . ? C9 C8 H8 108.1 . . ? C7 C8 H8 108.1 . . ? C14 C9 C10 119.20(15) . . ? C14 C9 C8 122.22(15) . . ? C10 C9 C8 118.58(15) . . ? C11 C10 C9 120.82(17) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 119.73(16) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C13 C12 C11 119.75(16) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.37(17) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C9 C14 C13 120.12(16) . . ? C9 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C2 N1 C6 117.99(16) . . ? C2 N2 C7 122.35(16) . . ? C2 N2 H2 112.7 . . ? C7 N2 H2 116.6 . . ? C8 O1 H1 104.6 . . ? 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 N1 C2 C3 C4 1.1(3) . . . . ? N2 C2 C3 C4 179.37(18) . . . . ? C2 C3 C4 C5 0.7(3) . . . . ? C3 C4 C5 C6 -1.6(3) . . . . ? C4 C5 C6 N1 0.8(3) . . . . ? N2 C7 C8 O1 -79.0(2) . . . . ? N2 C7 C8 C9 157.88(15) . . . . ? O1 C8 C9 C14 -13.0(2) . . . . ? C7 C8 C9 C14 111.06(18) . . . . ? O1 C8 C9 C10 166.30(15) . . . . ? C7 C8 C9 C10 -69.6(2) . . . . ? C14 C9 C10 C11 0.8(3) . . . . ? C8 C9 C10 C11 -178.56(16) . . . . ? C9 C10 C11 C12 0.2(3) . . . . ? C10 C11 C12 C13 -0.8(3) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C10 C9 C14 C13 -1.1(3) . . . . ? C8 C9 C14 C13 178.20(17) . . . . ? C12 C13 C14 C9 0.5(3) . . . . ? N2 C2 N1 C6 179.79(18) . . . . ? C3 C2 N1 C6 -1.9(3) . . . . ? C5 C6 N1 C2 1.0(3) . . . . ? N1 C2 N2 C7 -17.6(3) . . . . ? C3 C2 N2 C7 164.11(18) . . . . ? C8 C7 N2 C2 82.5(2) . . . . ? 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 N2 H2 O1 1.01 2.00 2.974(2) 161.0 1_455 O1 H1 N1 1.03 1.74 2.754(2) 166.2 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 32.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.223 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.046 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 827070' #TrackingRef '- cif1-5.cif' _audit_update_record ; 2011-11-03 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(2-pyrimidyl)amino-1-phenyloethanol ; _chemical_name_common N-(2-pyrimidyl)amino-1-phenyloethanol _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 N3 O' _chemical_formula_sum 'C12 H13 N3 O' _chemical_formula_weight 215.25 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/c' _symmetry_space_group_name_HALL '-P 2ybc' 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 5.6050(11) _cell_length_b 20.972(4) _cell_length_c 9.5000(19) _cell_angle_alpha 90.00 _cell_angle_beta 108.11(3) _cell_angle_gamma 90.00 _cell_volume 1061.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 41067 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 32.98 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The crystal was mounted with silicon grease on the tip of a nylon cryo-loop. Upon mounting, the crystal was quenched to 100 K in a nitrogen-gas stream supplied by an Oxford Cryo-Jet. Diffraction data were measured at the EMBL station X13 at the HASYLAB synchrotron, Hamburg, by rotation method. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.81620 _diffrn_radiation_type synchrotron _diffrn_radiation_source ; EMBL beamline X13, HASYLAB, Hamburg, Germany. ; _diffrn_radiation_monochromator 'Si111 single crystal' _diffrn_measurement_device_type 'MARCCD 165mm' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41074 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 32.98 _reflns_number_total 2574 _reflns_number_gt 2522 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MARCCD software' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _computing_molecular_graphics ; ORTEP-3 for Windows - Version 2.00, Univ. of Glasgow 2008. Mercury CSD 2.3 - new features for the visualization and investigation of crystal structures, C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek and P. A. Wood, J. Appl. Cryst., 41, 466-470, 2008. ; _computing_publication_material 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0834P)^2^+0.2472P] 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 SHELXL _refine_ls_extinction_coef 0.060(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2574 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1357 _refine_ls_wR_factor_gt 0.1321 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 C2 C -0.11941(18) 0.48265(5) 0.65496(10) 0.0208(2) Uani 1 1 d . A . C4 C -0.1028(2) 0.39265(5) 0.52229(11) 0.0252(2) Uani 1 1 d . . . H4 H -0.1799 0.3631 0.4492 0.030 Uiso 1 1 calc R . . C5 C 0.1495(2) 0.38455(5) 0.60055(12) 0.0274(3) Uani 1 1 d . . . H5 H 0.2417 0.3501 0.5839 0.033 Uiso 1 1 calc R . . C6 C 0.25489(19) 0.43071(5) 0.70440(12) 0.0267(3) Uani 1 1 d . . . H6 H 0.4246 0.4273 0.7572 0.032 Uiso 1 1 calc R . . C9 C -0.18601(18) 0.64220(5) 1.00456(11) 0.0223(2) Uani 1 1 d . A . C7 C -0.17755(19) 0.58350(5) 0.77781(11) 0.0248(2) Uani 1 1 d . A . H7A H -0.2245 0.6224 0.7207 0.030 Uiso 1 1 calc R . . H7B H 0.0042 0.5820 0.8161 0.030 Uiso 1 1 calc R . . C8 C -0.28431(19) 0.58489(5) 0.90682(11) 0.0239(2) Uani 1 1 d . . . H8 H -0.2422 0.5455 0.9646 0.029 Uiso 0.55(5) 1 calc PR A 1 H8' H -0.2202 0.5470 0.9670 0.029 Uiso 0.45(5) 1 d PR A 2 C10 C -0.34441(19) 0.69129(5) 1.01866(12) 0.0253(2) Uani 1 1 d . . . H10 H -0.5140 0.6898 0.9645 0.030 Uiso 1 1 calc R A . C11 C -0.2515(2) 0.74244(5) 1.11284(13) 0.0287(3) Uani 1 1 d . A . H11 H -0.3595 0.7748 1.1216 0.034 Uiso 1 1 calc R . . C12 C 0.0014(2) 0.74555(5) 1.19385(12) 0.0285(3) Uani 1 1 d . . . H12 H 0.0630 0.7796 1.2576 0.034 Uiso 1 1 calc R A . C13 C 0.16174(19) 0.69731(5) 1.17864(12) 0.0271(3) Uani 1 1 d . A . H13 H 0.3318 0.6993 1.2315 0.033 Uiso 1 1 calc R . . C14 C 0.06887(19) 0.64609(5) 1.08486(11) 0.0251(2) Uani 1 1 d . . . H14 H 0.1776 0.6140 1.0754 0.030 Uiso 1 1 calc R A . N1 N 0.12674(16) 0.48028(4) 0.73367(9) 0.0241(2) Uani 1 1 d . . . N3 N -0.23939(15) 0.44081(4) 0.54723(9) 0.0226(2) Uani 1 1 d . . . N2 N -0.26693(16) 0.52914(4) 0.68169(9) 0.0235(2) Uani 1 1 d . . . H2 H -0.4300 0.5335 0.6069 0.028 Uiso 1 1 d R A . O1 O -0.5543(14) 0.5907(3) 0.8417(9) 0.0315(12) Uani 0.55(5) 1 d P A 1 H1 H -0.6360 0.5524 0.8075 0.038 Uiso 0.55(5) 1 d PR A 1 O1' O -0.540(2) 0.5841(9) 0.875(3) 0.055(3) Uani 0.45(5) 1 d P A 2 H1' H -0.5940 0.5460 0.8405 0.067 Uiso 0.45(5) 1 d PR A 2 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 C2 0.0215(5) 0.0221(5) 0.0183(4) 0.0026(3) 0.0053(4) -0.0026(3) C4 0.0277(5) 0.0245(5) 0.0237(5) 0.0000(4) 0.0081(4) 0.0004(4) C5 0.0274(5) 0.0282(5) 0.0276(5) 0.0046(4) 0.0099(4) 0.0054(4) C6 0.0214(5) 0.0301(5) 0.0272(5) 0.0071(4) 0.0055(4) 0.0011(4) C9 0.0228(5) 0.0227(5) 0.0224(5) -0.0008(3) 0.0085(4) -0.0029(3) C7 0.0270(5) 0.0235(5) 0.0239(5) -0.0037(3) 0.0081(4) -0.0057(3) C8 0.0219(5) 0.0246(5) 0.0261(5) -0.0042(3) 0.0088(4) -0.0039(3) C10 0.0215(4) 0.0244(5) 0.0287(5) -0.0003(4) 0.0059(4) -0.0009(3) C11 0.0278(5) 0.0217(5) 0.0354(6) -0.0030(4) 0.0080(4) 0.0012(4) C12 0.0298(5) 0.0236(5) 0.0301(5) -0.0051(4) 0.0065(4) -0.0048(4) C13 0.0222(5) 0.0311(5) 0.0256(5) -0.0032(4) 0.0039(4) -0.0029(4) C14 0.0221(5) 0.0268(5) 0.0258(5) -0.0024(4) 0.0067(4) 0.0004(3) N1 0.0213(4) 0.0256(4) 0.0225(4) 0.0041(3) 0.0025(3) -0.0023(3) N3 0.0220(4) 0.0241(4) 0.0203(4) -0.0013(3) 0.0045(3) -0.0006(3) N2 0.0222(4) 0.0244(4) 0.0222(4) -0.0039(3) 0.0045(3) -0.0017(3) O1 0.0160(12) 0.0327(19) 0.043(2) -0.0165(18) 0.0054(15) -0.0011(14) O1' 0.029(3) 0.067(4) 0.079(7) -0.054(4) 0.030(3) -0.027(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 C2 N1 1.3504(14) . ? C2 N2 1.3526(13) . ? C2 N3 1.3570(13) . ? C4 N3 1.3324(13) . ? C4 C5 1.3886(15) . ? C4 H4 0.9300 . ? C5 C6 1.3772(16) . ? C5 H5 0.9300 . ? C6 N1 1.3410(14) . ? C6 H6 0.9300 . ? C9 C10 1.3929(14) . ? C9 C14 1.3971(15) . ? C9 C8 1.5141(13) . ? C7 N2 1.4492(12) . ? C7 C8 1.5221(14) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O1' 1.369(11) . ? C8 O1 1.451(7) . ? C8 H8 0.9800 . ? C8 H8' 0.9800 . ? C10 C11 1.3901(14) . ? C10 H10 0.9300 . ? C11 C12 1.3887(16) . ? C11 H11 0.9300 . ? C12 C13 1.3901(15) . ? C12 H12 0.9300 . ? C13 C14 1.3894(14) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? N2 H2 0.9721 . ? O1 H1 0.9321 . ? O1 H1' 0.9638 . ? O1' H1 0.9630 . ? O1' H1' 0.8814 . ? 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 N1 C2 N2 120.10(9) . . ? N1 C2 N3 125.12(9) . . ? N2 C2 N3 114.78(9) . . ? N3 C4 C5 122.92(10) . . ? N3 C4 H4 118.5 . . ? C5 C4 H4 118.5 . . ? C6 C5 C4 115.85(10) . . ? C6 C5 H5 122.1 . . ? C4 C5 H5 122.1 . . ? N1 C6 C5 123.74(10) . . ? N1 C6 H6 118.1 . . ? C5 C6 H6 118.1 . . ? C10 C9 C14 118.59(9) . . ? C10 C9 C8 121.63(9) . . ? C14 C9 C8 119.77(9) . . ? N2 C7 C8 112.14(8) . . ? N2 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? N2 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? O1' C8 O1 13.0(13) . . ? O1' C8 C9 107.5(5) . . ? O1 C8 C9 109.1(3) . . ? O1' C8 C7 117.9(12) . . ? O1 C8 C7 106.1(3) . . ? C9 C8 C7 110.47(8) . . ? O1' C8 H8 99.7 . . ? O1 C8 H8 110.4 . . ? C9 C8 H8 110.4 . . ? C7 C8 H8 110.4 . . ? O1' C8 H8' 106.8 . . ? O1 C8 H8' 117.5 . . ? C9 C8 H8' 106.8 . . ? C7 C8 H8' 106.8 . . ? H8 C8 H8' 7.2 . . ? C11 C10 C9 120.65(10) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 120.43(10) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.32(9) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 120.26(10) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C9 120.72(9) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? C6 N1 C2 115.76(9) . . ? C4 N3 C2 116.54(9) . . ? C2 N2 C7 125.01(9) . . ? C2 N2 H2 114.9 . . ? C7 N2 H2 116.7 . . ? C8 O1 H1 114.2 . . ? C8 O1 H1' 97.4 . . ? H1 O1 H1' 21.5 . . ? C8 O1' H1 119.0 . . ? C8 O1' H1' 107.9 . . ? H1 O1' H1' 21.6 . . ? 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 N3 C4 C5 C6 -1.73(15) . . . . ? C4 C5 C6 N1 1.46(15) . . . . ? C10 C9 C8 O1' -15.4(14) . . . . ? C14 C9 C8 O1' 163.6(14) . . . . ? C10 C9 C8 O1 -1.8(4) . . . . ? C14 C9 C8 O1 177.3(3) . . . . ? C10 C9 C8 C7 114.44(11) . . . . ? C14 C9 C8 C7 -66.51(12) . . . . ? N2 C7 C8 O1' -56.0(9) . . . . ? N2 C7 C8 O1 -62.1(3) . . . . ? N2 C7 C8 C9 179.86(8) . . . . ? C14 C9 C10 C11 -1.22(15) . . . . ? C8 C9 C10 C11 177.85(9) . . . . ? C9 C10 C11 C12 0.36(16) . . . . ? C10 C11 C12 C13 0.70(17) . . . . ? C11 C12 C13 C14 -0.89(16) . . . . ? C12 C13 C14 C9 0.02(16) . . . . ? C10 C9 C14 C13 1.03(15) . . . . ? C8 C9 C14 C13 -178.05(9) . . . . ? C5 C6 N1 C2 0.62(15) . . . . ? N2 C2 N1 C6 176.81(8) . . . . ? N3 C2 N1 C6 -2.75(14) . . . . ? C5 C4 N3 C2 -0.11(15) . . . . ? N1 C2 N3 C4 2.51(14) . . . . ? N2 C2 N3 C4 -177.07(8) . . . . ? N1 C2 N2 C7 8.31(14) . . . . ? N3 C2 N2 C7 -172.09(8) . . . . ? C8 C7 N2 C2 -118.76(10) . . . . ? 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 O1 H1 N1 0.93 1.99 2.911(9) 168.3 1_455 O1' H1' N1 0.88 2.10 2.911(10) 153.5 1_455 N2 H2 N3 0.97 2.04 3.0069(16) 170.1 3_466 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 32.98 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.245 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.048 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 827071' #TrackingRef 'cif1-5.cif' _audit_update_record ; 2011-02-07 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis{N-(2-pyridyl)aminoethyl}carbonate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H18 N4 O3' _chemical_formula_sum 'C15 H18 N4 O3' _chemical_formula_weight 302.33 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 C2/c _symmetry_space_group_name_HALL '-C 2yc' 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 32.334(7) _cell_length_b 5.7910(12) _cell_length_c 16.392(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.42(3) _cell_angle_gamma 90.00 _cell_volume 2972.7(10) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.80800 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3622 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 32.59 _reflns_number_total 3622 _reflns_number_gt 3471 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 for Windows - Version 2.00, Univ. of Glasgow 2008. Mercury CSD 2.3 - new features for the visualization and investigation of crystal structures, C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek and P. A. Wood, J. Appl. Cryst., 41, 466-470, 2008. ; _computing_publication_material 'Shelxl-97 (Sheldrick, 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. 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^)+(0.0701P)^2^+0.6528P] 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 SHELXL _refine_ls_extinction_coef 0.030(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3622 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1283 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 C2 C 0.43953(3) -0.41682(16) 0.41349(6) 0.0440(2) Uani 1 1 d . . . C2' C 0.24150(3) 0.56992(16) 0.61738(6) 0.0421(2) Uani 1 1 d . . . C3 C 0.41696(4) -0.58945(19) 0.36035(7) 0.0542(3) Uani 1 1 d . . . H3 H 0.4037 -0.7088 0.3821 0.065 Uiso 1 1 calc R . . C3' C 0.23162(4) 0.42462(18) 0.67801(7) 0.0505(3) Uani 1 1 d . . . H3' H 0.2510 0.3137 0.7051 0.061 Uiso 1 1 calc R . . C4 C 0.41486(5) -0.5789(2) 0.27629(8) 0.0670(4) Uani 1 1 d . . . H4 H 0.4007 -0.6931 0.2400 0.080 Uiso 1 1 calc R . . C4' C 0.19282(4) 0.4485(2) 0.69687(8) 0.0578(3) Uani 1 1 d . . . H4' H 0.1857 0.3528 0.7368 0.069 Uiso 1 1 calc R . . C5 C 0.43419(5) -0.3949(3) 0.24564(8) 0.0729(4) Uani 1 1 d . . . H5 H 0.4332 -0.3830 0.1886 0.088 Uiso 1 1 calc R . . C5' C 0.16432(4) 0.6153(2) 0.65636(8) 0.0587(3) Uani 1 1 d . . . H5' H 0.1380 0.6358 0.6688 0.070 Uiso 1 1 calc R . . C6' C 0.17631(3) 0.7487(2) 0.59727(7) 0.0566(3) Uani 1 1 d . . . H6' H 0.1572 0.8603 0.5697 0.068 Uiso 1 1 calc R . . C6 C 0.45461(4) -0.2324(3) 0.30156(8) 0.0667(3) Uani 1 1 d . . . H6 H 0.4671 -0.1085 0.2806 0.080 Uiso 1 1 calc R . . C7' C 0.31378(3) 0.40511(17) 0.62826(7) 0.0474(2) Uani 1 1 d . . . H7'1 H 0.3157 0.3770 0.6874 0.057 Uiso 1 1 calc R . . H7'2 H 0.3405 0.4729 0.6237 0.057 Uiso 1 1 calc R . . C7 C 0.46607(3) -0.26189(18) 0.55699(6) 0.0480(3) Uani 1 1 d . . . H7A H 0.4932 -0.2303 0.5442 0.058 Uiso 1 1 calc R . . H7B H 0.4720 -0.3269 0.6132 0.058 Uiso 1 1 calc R . . C8' C 0.30690(3) 0.17840(19) 0.58092(7) 0.0505(3) Uani 1 1 d . . . H8'1 H 0.2823 0.1008 0.5920 0.061 Uiso 1 1 calc R . . H8'2 H 0.3009 0.2089 0.5209 0.061 Uiso 1 1 calc R . . C8 C 0.44248(3) -0.03803(18) 0.55636(7) 0.0504(3) Uani 1 1 d . . . H8A H 0.4610 0.0755 0.5908 0.060 Uiso 1 1 calc R . . H8B H 0.4335 0.0212 0.4993 0.060 Uiso 1 1 calc R . . C9 C 0.37545(3) 0.08055(15) 0.57013(6) 0.0421(2) Uani 1 1 d . . . N1' N 0.21374(3) 0.72937(15) 0.57646(6) 0.0504(2) Uani 1 1 d . . . N1 N 0.45794(3) -0.23898(16) 0.38468(6) 0.0532(2) Uani 1 1 d . . . N2 N 0.44346(3) -0.43007(15) 0.49829(6) 0.0488(2) Uani 1 1 d . . . H2 H 0.4252 -0.5255 0.5165 0.059 Uiso 1 1 d R . . N2' N 0.27942(3) 0.56438(16) 0.59546(6) 0.0509(2) Uani 1 1 d . . . H2' H 0.2816 0.6491 0.5473 0.061 Uiso 1 1 d R . . O1 O 0.40540(2) -0.08022(12) 0.58961(5) 0.0490(2) Uani 1 1 d . . . O1' O 0.34393(2) 0.02718(13) 0.60505(5) 0.0503(2) Uani 1 1 d . . . O2 O 0.37661(3) 0.24814(13) 0.52759(5) 0.0547(2) 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 C2 0.0379(4) 0.0451(5) 0.0514(5) 0.0050(4) 0.0157(4) 0.0079(3) C2' 0.0414(4) 0.0408(5) 0.0442(5) -0.0030(3) 0.0110(3) 0.0035(3) C3 0.0533(6) 0.0503(6) 0.0577(6) 0.0011(4) 0.0112(4) 0.0042(4) C3' 0.0506(5) 0.0488(5) 0.0539(5) 0.0056(4) 0.0164(4) 0.0063(4) C4 0.0686(7) 0.0721(8) 0.0546(6) -0.0060(5) 0.0047(5) 0.0142(6) C4' 0.0564(6) 0.0605(6) 0.0617(6) 0.0027(5) 0.0246(5) -0.0022(5) C5 0.0760(8) 0.0964(10) 0.0484(6) 0.0090(6) 0.0190(5) 0.0180(7) C5' 0.0425(5) 0.0700(7) 0.0663(7) -0.0069(5) 0.0190(4) 0.0033(5) C6' 0.0465(5) 0.0630(7) 0.0597(6) 0.0005(5) 0.0120(4) 0.0159(4) C6 0.0637(7) 0.0809(9) 0.0623(7) 0.0178(6) 0.0286(5) 0.0039(6) C7' 0.0392(5) 0.0502(5) 0.0524(5) -0.0016(4) 0.0109(4) 0.0060(4) C7 0.0407(5) 0.0525(6) 0.0520(5) 0.0011(4) 0.0139(4) 0.0072(4) C8' 0.0364(4) 0.0493(5) 0.0666(6) -0.0041(5) 0.0144(4) 0.0019(4) C8 0.0442(5) 0.0464(5) 0.0664(6) -0.0017(4) 0.0246(4) 0.0009(4) C9 0.0416(5) 0.0402(5) 0.0468(5) -0.0008(3) 0.0153(4) 0.0015(3) N1' 0.0494(5) 0.0509(5) 0.0522(5) 0.0052(3) 0.0151(3) 0.0127(4) N1 0.0472(5) 0.0582(5) 0.0582(5) 0.0091(4) 0.0207(4) -0.0002(4) N2 0.0545(5) 0.0449(4) 0.0513(5) 0.0022(3) 0.0214(4) -0.0013(3) N2' 0.0459(5) 0.0512(5) 0.0599(5) 0.0107(4) 0.0211(4) 0.0107(3) O1 0.0457(4) 0.0466(4) 0.0603(4) 0.0070(3) 0.0241(3) 0.0090(3) O1' 0.0444(4) 0.0443(4) 0.0689(5) 0.0068(3) 0.0265(3) 0.0055(3) O2 0.0551(4) 0.0487(4) 0.0666(5) 0.0125(3) 0.0270(4) 0.0068(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 C2 N1 1.3335(13) . ? C2 N2 1.3660(13) . ? C2 C3 1.4050(15) . ? C2' N1' 1.3447(12) . ? C2' N2' 1.3612(13) . ? C2' C3' 1.3985(15) . ? C3 C4 1.3640(18) . ? C3 H3 0.9300 . ? C3' C4' 1.3719(16) . ? C3' H3' 0.9300 . ? C4 C5 1.391(2) . ? C4 H4 0.9300 . ? C4' C5' 1.3851(17) . ? C4' H4' 0.9300 . ? C5 C6 1.364(2) . ? C5 H5 0.9300 . ? C5' C6' 1.3682(18) . ? C5' H5' 0.9300 . ? C6' N1' 1.3416(14) . ? C6' H6' 0.9300 . ? C6 N1 1.3402(16) . ? C6 H6 0.9300 . ? C7' N2' 1.4411(13) . ? C7' C8' 1.5131(15) . ? C7' H7'1 0.9700 . ? C7' H7'2 0.9700 . ? C7 N2 1.4348(14) . ? C7 C8 1.5028(14) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8' O1' 1.4564(12) . ? C8' H8'1 0.9700 . ? C8' H8'2 0.9700 . ? C8 O1 1.4561(12) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O2 1.2010(12) . ? C9 O1 1.3237(12) . ? C9 O1' 1.3239(12) . ? N2 H2 0.9126 . ? N2' H2' 0.9467 . ? 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 N1 C2 N2 117.85(9) . . ? N1 C2 C3 122.59(10) . . ? N2 C2 C3 119.56(9) . . ? N1' C2' N2' 114.68(9) . . ? N1' C2' C3' 121.70(10) . . ? N2' C2' C3' 123.61(9) . . ? C4 C3 C2 118.82(12) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C4' C3' C2' 118.88(10) . . ? C4' C3' H3' 120.6 . . ? C2' C3' H3' 120.6 . . ? C3 C4 C5 119.03(13) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C3' C4' C5' 119.92(11) . . ? C3' C4' H4' 120.0 . . ? C5' C4' H4' 120.0 . . ? C6 C5 C4 118.14(12) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C6' C5' C4' 117.47(10) . . ? C6' C5' H5' 121.3 . . ? C4' C5' H5' 121.3 . . ? N1' C6' C5' 124.44(10) . . ? N1' C6' H6' 117.8 . . ? C5' C6' H6' 117.8 . . ? N1 C6 C5 124.51(12) . . ? N1 C6 H6 117.7 . . ? C5 C6 H6 117.7 . . ? N2' C7' C8' 111.27(8) . . ? N2' C7' H7'1 109.4 . . ? C8' C7' H7'1 109.4 . . ? N2' C7' H7'2 109.4 . . ? C8' C7' H7'2 109.4 . . ? H7'1 C7' H7'2 108.0 . . ? N2 C7 C8 114.07(9) . . ? N2 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? N2 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? O1' C8' C7' 112.11(8) . . ? O1' C8' H8'1 109.2 . . ? C7' C8' H8'1 109.2 . . ? O1' C8' H8'2 109.2 . . ? C7' C8' H8'2 109.2 . . ? H8'1 C8' H8'2 107.9 . . ? O1 C8 C7 108.45(8) . . ? O1 C8 H8A 110.0 . . ? C7 C8 H8A 110.0 . . ? O1 C8 H8B 110.0 . . ? C7 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? O2 C9 O1 125.57(9) . . ? O2 C9 O1' 125.33(9) . . ? O1 C9 O1' 109.09(8) . . ? C6' N1' C2' 117.57(9) . . ? C2 N1 C6 116.88(11) . . ? C2 N2 C7 123.16(9) . . ? C2 N2 H2 117.6 . . ? C7 N2 H2 117.1 . . ? C2' N2' C7' 125.32(9) . . ? C2' N2' H2' 117.9 . . ? C7' N2' H2' 115.6 . . ? C9 O1 C8 114.38(8) . . ? C9 O1' C8' 114.30(8) . . ? 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 N1 C2 C3 C4 2.06(16) . . . . ? N2 C2 C3 C4 -177.26(10) . . . . ? N1' C2' C3' C4' -0.99(16) . . . . ? N2' C2' C3' C4' 178.39(10) . . . . ? C2 C3 C4 C5 -1.58(18) . . . . ? C2' C3' C4' C5' -0.34(18) . . . . ? C3 C4 C5 C6 0.2(2) . . . . ? C3' C4' C5' C6' 0.98(18) . . . . ? C4' C5' C6' N1' -0.37(19) . . . . ? C4 C5 C6 N1 1.0(2) . . . . ? N2' C7' C8' O1' 172.01(8) . . . . ? N2 C7 C8 O1 68.19(11) . . . . ? C5' C6' N1' C2' -0.91(17) . . . . ? N2' C2' N1' C6' -177.84(9) . . . . ? C3' C2' N1' C6' 1.59(15) . . . . ? N2 C2 N1 C6 178.36(9) . . . . ? C3 C2 N1 C6 -0.96(15) . . . . ? C5 C6 N1 C2 -0.58(19) . . . . ? N1 C2 N2 C7 0.41(14) . . . . ? C3 C2 N2 C7 179.75(9) . . . . ? C8 C7 N2 C2 75.06(12) . . . . ? N1' C2' N2' C7' -178.01(9) . . . . ? C3' C2' N2' C7' 2.57(17) . . . . ? C8' C7' N2' C2' 83.89(13) . . . . ? O2 C9 O1 C8 1.42(15) . . . . ? O1' C9 O1 C8 -178.59(8) . . . . ? C7 C8 O1 C9 -161.05(9) . . . . ? O2 C9 O1' C8' 6.15(15) . . . . ? O1 C9 O1' C8' -173.84(8) . . . . ? C7' C8' O1' C9 -78.63(11) . . . . ? 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 N2' H2' N1' 0.95 2.19 3.1188(14) 167.5 7_566 N2 H2 O2 0.91 2.09 2.9819(12) 166.3 1_545 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 32.59 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.151 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.031 #===END