#------------------------------------------------------------------------------ #$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2204862.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2204862 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _[local]_cod_cif_authors_sg_H-M 'P 21/n' loop_ _publ_author_name 'Shyamaprosad Goswami' 'Swapan Dey' 'Suchada Chantrapromma' 'Hoong-Kun Fun' _publ_section_title ; N-[6-(Hydroxymethyl)pyridin-2-yl]-2,2-dimethylpropanamide ; _journal_issue 1 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o105 _journal_page_last o107 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C11 H16 N2 O2' _chemical_formula_moiety 'C11 H16 N2 O2' _chemical_formula_sum 'C11 H16 N2 O2' _chemical_formula_weight 208.26 _chemical_melting_point .39E-305 _chemical_name_common 2-Pivaloyl-2-amino-6-hydroxymethylpyridine _chemical_name_systematic ; N-[6-(Hydroxymethyl)pyridin-2-yl]-2,2-dimethylpropanamide ; _symmetry_cell_setting Monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 94.486(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.8330(6) _cell_length_b 10.3313(10) _cell_length_c 16.1635(15) _cell_measurement_reflns_used 2858 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.31 _cell_measurement_theta_min 2.34 _cell_volume 1137.55(18) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector diffractometer' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 6663 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.34 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.219 _refine_diff_density_min -0.187 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 2584 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.083 _refine_ls_R_factor_all 0.0727 _refine_ls_R_factor_gt 0.0528 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+0.3411P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1310 _refine_ls_wR_factor_ref 0.1461 _reflns_number_gt 1929 _reflns_number_total 2609 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file ci6500.cif 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' 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol N1 0.2280(2) 0.42001(14) 0.47186(9) 0.0419(4) Uani d . 1 N N2 0.1085(2) 0.46071(15) 0.33796(9) 0.0460(4) Uani d . 1 N C6 0.3839(3) 0.3948(2) 0.61079(13) 0.0576(5) Uani d . 1 C O2 -0.1232(3) 0.36860(17) 0.24967(8) 0.0729(5) Uani d . 1 O C1 0.0923(2) 0.38936(16) 0.41124(10) 0.0395(4) Uani d . 1 C C2 -0.0505(3) 0.29564(19) 0.42011(12) 0.0501(5) Uani d . 1 C C3 -0.0475(3) 0.2315(2) 0.49488(12) 0.0559(5) Uani d . 1 C C4 0.0932(3) 0.26042(19) 0.55766(12) 0.0500(5) Uani d . 1 C C5 0.2279(3) 0.35623(18) 0.54443(10) 0.0435(4) Uani d . 1 C O1 0.5750(2) 0.36080(16) 0.58998(10) 0.0660(5) Uani d . 1 O C8 0.0088(3) 0.44607(17) 0.26224(11) 0.0440(4) Uani d . 1 C C9 0.0779(3) 0.53425(17) 0.19354(11) 0.0464(4) Uani d . 1 C C10 -0.0616(5) 0.5165(3) 0.11587(14) 0.0855(9) Uani d . 1 C H10A -0.0527 0.4291 0.0963 0.128 Uiso calc R 1 H H10B -0.0260 0.5752 0.0735 0.128 Uiso calc R 1 H H10C -0.1937 0.5339 0.1289 0.128 Uiso calc R 1 H C11 0.2849(4) 0.4950(3) 0.17548(16) 0.0864(9) Uani d . 1 C H11A 0.2858 0.4054 0.1598 0.130 Uiso calc R 1 H H11B 0.3722 0.5077 0.2243 0.130 Uiso calc R 1 H H11C 0.3272 0.5470 0.1310 0.130 Uiso calc R 1 H C12 0.0754(4) 0.67600(19) 0.22009(14) 0.0699(6) Uani d . 1 C H12A 0.1102 0.7298 0.1751 0.105 Uiso calc R 1 H H12B 0.1682 0.6888 0.2671 0.105 Uiso calc R 1 H H12C -0.0537 0.6986 0.2348 0.105 Uiso calc R 1 H H2 -0.144(3) 0.280(2) 0.3774(14) 0.062(6) Uiso d . 1 H H3 -0.143(3) 0.168(2) 0.5017(13) 0.062(6) Uiso d . 1 H H4 0.102(3) 0.2177(19) 0.6090(13) 0.049(5) Uiso d . 1 H H2A 0.197(3) 0.517(2) 0.3433(12) 0.050(6) Uiso d . 1 H H6A 0.382(3) 0.491(2) 0.6196(14) 0.068(7) Uiso d . 1 H H6B 0.358(3) 0.348(2) 0.6624(15) 0.070(7) Uiso d . 1 H H1A 0.620(4) 0.412(3) 0.5512(19) 0.109(11) Uiso d . 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0426(8) 0.0442(8) 0.0392(8) -0.0008(6) 0.0040(6) 0.0037(6) N2 0.0527(9) 0.0453(9) 0.0394(8) -0.0108(7) 0.0007(7) 0.0043(6) C6 0.0559(12) 0.0699(14) 0.0459(11) -0.0033(10) -0.0031(9) 0.0098(10) O2 0.0930(12) 0.0800(10) 0.0442(8) -0.0391(9) -0.0054(7) 0.0021(7) C1 0.0431(9) 0.0385(8) 0.0375(8) 0.0019(7) 0.0064(7) 0.0003(7) C2 0.0544(12) 0.0516(11) 0.0442(10) -0.0101(9) 0.0020(9) -0.0002(8) C3 0.0621(13) 0.0557(11) 0.0507(11) -0.0164(10) 0.0094(9) 0.0048(9) C4 0.0560(11) 0.0547(11) 0.0401(10) -0.0020(9) 0.0094(8) 0.0087(8) C5 0.0427(9) 0.0484(10) 0.0397(9) 0.0054(7) 0.0060(7) 0.0029(7) O1 0.0486(8) 0.0727(10) 0.0753(10) -0.0059(7) -0.0047(7) 0.0251(8) C8 0.0531(11) 0.0411(9) 0.0378(9) -0.0018(8) 0.0037(8) -0.0031(7) C9 0.0614(12) 0.0421(9) 0.0356(9) 0.0002(8) 0.0041(8) 0.0006(7) C10 0.125(2) 0.0825(17) 0.0461(12) -0.0250(16) -0.0156(13) 0.0147(11) C11 0.0934(19) 0.0918(18) 0.0795(17) 0.0232(15) 0.0419(15) 0.0305(14) C12 0.1094(19) 0.0439(11) 0.0572(13) -0.0014(12) 0.0118(12) 0.0056(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C1 1.334(2) yes N1 C5 1.345(2) yes N2 C8 1.362(2) yes N2 C1 1.407(2) yes N2 H2A 0.84(2) ? C6 O1 1.418(3) yes C6 C5 1.506(3) ? C6 H6A 1.00(2) ? C6 H6B 0.99(2) ? O2 C8 1.211(2) yes C1 C2 1.390(3) ? C2 C3 1.377(3) ? C2 H2 0.92(2) ? C3 C4 1.375(3) ? C3 H3 0.94(2) ? C4 C5 1.379(3) ? C4 H4 0.94(2) ? O1 H1A 0.89(3) ? C8 C9 1.539(2) ? C9 C11 1.522(3) ? C9 C12 1.527(3) ? C9 C10 1.527(3) ? C10 H10A 0.96 ? C10 H10B 0.96 ? C10 H10C 0.96 ? C11 H11A 0.96 ? C11 H11B 0.96 ? C11 H11C 0.96 ? C12 H12A 0.96 ? C12 H12B 0.96 ? C12 H12C 0.96 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 N1 C5 118.45(15) yes C8 N2 C1 129.17(16) yes C8 N2 H2A 118.4(14) ? C1 N2 H2A 112.3(14) ? O1 C6 C5 112.30(18) ? O1 C6 H6A 107.7(13) ? C5 C6 H6A 110.2(13) ? O1 C6 H6B 107.9(13) ? C5 C6 H6B 108.0(13) ? H6A C6 H6B 110.8(19) ? N1 C1 C2 122.89(16) ? N1 C1 N2 113.46(15) ? C2 C1 N2 123.64(16) ? C3 C2 C1 117.61(18) ? C3 C2 H2 122.4(14) ? C1 C2 H2 120.0(14) ? C4 C3 C2 120.30(19) ? C4 C3 H3 121.3(13) ? C2 C3 H3 118.5(13) ? C3 C4 C5 118.55(18) ? C3 C4 H4 123.0(12) ? C5 C4 H4 118.5(12) ? N1 C5 C4 122.19(17) ? N1 C5 C6 116.25(17) ? C4 C5 C6 121.56(17) ? C6 O1 H1A 113(2) ? O2 C8 N2 122.54(17) yes O2 C8 C9 122.45(16) ? N2 C8 C9 115.01(16) yes C11 C9 C12 109.9(2) yes C11 C9 C10 109.9(2) yes C12 C9 C10 109.08(18) yes C11 C9 C8 108.82(16) yes C12 C9 C8 110.75(15) ? C10 C9 C8 108.39(17) ? C9 C10 H10A 109.5 ? C9 C10 H10B 109.5 ? H10A C10 H10B 109.5 ? C9 C10 H10C 109.5 ? H10A C10 H10C 109.5 ? H10B C10 H10C 109.5 ? C9 C11 H11A 109.5 ? C9 C11 H11B 109.5 ? H11A C11 H11B 109.5 ? C9 C11 H11C 109.5 ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? C9 C12 H12A 109.5 ? C9 C12 H12B 109.5 ? H12A C12 H12B 109.5 ? C9 C12 H12C 109.5 ? H12A C12 H12C 109.5 ? H12B C12 H12C 109.5 ? 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_publ_flag C5 N1 C1 C2 0.8(3) ? C5 N1 C1 N2 -179.06(15) ? C8 N2 C1 N1 172.80(17) ? C8 N2 C1 C2 -7.1(3) yes N1 C1 C2 C3 -0.9(3) ? N2 C1 C2 C3 178.94(18) yes C1 C2 C3 C4 -0.1(3) ? C2 C3 C4 C5 1.2(3) ? C1 N1 C5 C4 0.4(3) ? C1 N1 C5 C6 -179.88(16) ? C3 C4 C5 N1 -1.4(3) ? C3 C4 C5 C6 178.9(2) ? O1 C6 C5 N1 -67.6(2) ? O1 C6 C5 C4 112.2(2) yes C1 N2 C8 O2 4.6(3) yes C1 N2 C8 C9 -174.75(17) ? O2 C8 C9 C11 -112.8(2) ? N2 C8 C9 C11 66.5(2) ? O2 C8 C9 C12 126.2(2) ? N2 C8 C9 C12 -54.4(2) ? O2 C8 C9 C10 6.6(3) ? N2 C8 C9 C10 -174.02(18) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1A N1 3_666 0.89(3) 2.07(3) 2.855(2) 146(3) yes N2 H2A O1 3_666 0.84(2) 2.22(2) 3.007(2) 157(2) yes C2 H2 O2 1_555 0.92(2) 2.27(2) 2.862(2) 122(2) yes _cod_database_code 2204862