#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2200308.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_2200308 loop_ _publ_author_name 'Chen, Zhen-Feng' 'Xie, Yong-Rong' 'Fun, Hoong-Kun' 'Chantrapromma, Suchada' 'Razak, Ibrahim Abdul' 'Xiong, Ren-Gen' 'You, Xiao-Zeng' _publ_section_title ; 4-[(3-Pyridylamino)methyl]phenol ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o411 _journal_page_last o413 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C12 H12 N2 O' _chemical_formula_moiety 'C12 H12 N2 O' _chemical_formula_sum 'C12 H12 N2 O' _chemical_formula_weight 200.24 _chemical_name_systematic ; 4-[(3-Pyridylamino)methyl]phenol ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.5392(2) _cell_length_b 7.60770(10) _cell_length_c 20.3127(5) _cell_measurement_reflns_used 2653 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.53 _cell_measurement_theta_min 2.01 _cell_volume 1010.52(4) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction 'SAINT and SADABS (Sheldrick, 1996)' _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)' _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 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0787 _diffrn_reflns_av_sigmaI/netI .0876 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 6968 _diffrn_reflns_theta_full 27.47 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_min 2.01 _exptl_absorpt_coefficient_mu .086 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular block' _exptl_crystal_F_000 424 _exptl_crystal_size_max .20 _exptl_crystal_size_mid .14 _exptl_crystal_size_min .01 _refine_diff_density_max .159 _refine_diff_density_min -.187 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .990 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 144 _refine_ls_number_reflns 2308 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .990 _refine_ls_R_factor_all .1100 _refine_ls_R_factor_gt .0577 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0525P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1333 _reflns_number_gt 1400 _reflns_number_total 2308 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na6064.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2200308 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 O1 -.1374(3) -.2800(3) .13307(10) .0513(6) Uani d . 1 O N1 .4632(4) -.0819(3) .36769(12) .0474(7) Uani d . 1 N N2 .6644(4) .0710(3) .52458(11) .0565(7) Uani d . 1 N C1 .1771(4) -.2875(4) .28009(14) .0429(7) Uani d . 1 C H1C .1673 -.3289 .3230 .051 Uiso calc R 1 H C2 .0173(5) -.3155(4) .23731(13) .0423(7) Uani d . 1 C H2B -.0978 -.3767 .2515 .051 Uiso calc R 1 H C3 .0265(4) -.2536(3) .17339(12) .0382(7) Uani d . 1 C C4 .2022(4) -.1703(4) .15207(13) .0434(7) Uani d . 1 C H4A .2124 -.1317 .1088 .052 Uiso calc R 1 H C5 .3637(5) -.1444(3) .19547(13) .0423(7) Uani d . 1 C H5A .4819 -.0895 .1805 .051 Uiso calc R 1 H C6 .3529(4) -.1985(3) .26062(12) .0378(7) Uani d . 1 C C7 .5280(5) -.1666(4) .30710(13) .0449(7) Uani d . 1 C H7A .5924 -.2780 .3176 .054 Uiso calc R 1 H H7B .6291 -.0933 .2855 .054 Uiso calc R 1 H C8 .5991(4) -.0572(3) .41807(12) .0387(6) Uani d . 1 C C9 .5452(5) .0443(4) .47296(13) .0489(8) Uani d . 1 C H9A .4166 .0965 .4731 .059 Uiso calc R 1 H C10 .8513(6) -.0047(5) .52411(16) .0633(9) Uani d . 1 C H10A .9368 .0117 .5602 .076 Uiso calc R 1 H C11 .9195(5) -.1041(4) .47280(15) .0547(8) Uani d . 1 C H11A 1.0489 -.1546 .4742 .066 Uiso calc R 1 H C12 .7959(4) -.1290(4) .41932(14) .0472(8) Uani d . 1 C H12A .8430 -.1939 .3836 .057 Uiso calc R 1 H H1A -.132(6) -.209(5) .0927(18) .099(13) Uiso d . 1 H H1B .364(5) -.004(4) .3607(16) .077(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 O1 .0491(12) .0528(13) .0519(12) -.0139(10) -.0053(11) .0062(10) N1 .0466(15) .0442(14) .0514(14) .0119(13) -.0039(13) -.0065(12) N2 .0592(17) .0591(17) .0512(15) -.0067(14) -.0055(15) -.0101(13) C1 .0475(18) .0395(17) .0417(14) -.0016(14) .0079(15) .0052(12) C2 .0416(16) .0336(14) .0518(18) -.0043(13) .0103(15) .0045(13) C3 .0416(17) .0311(14) .0420(15) -.0008(13) .0041(14) -.0034(12) C4 .0516(18) .0425(16) .0362(14) -.0050(14) .0119(15) -.0013(12) C5 .0399(16) .0379(15) .0490(17) -.0068(13) .0112(15) -.0048(13) C6 .0392(16) .0315(15) .0429(16) .0062(13) .0069(14) -.0026(12) C7 .0433(17) .0412(16) .0501(17) .0026(14) .0006(15) -.0030(13) C8 .0415(15) .0315(14) .0431(15) -.0012(12) -.0048(14) .0034(13) C9 .0507(18) .0430(17) .0530(17) .0017(15) -.0030(17) -.0029(14) C10 .060(2) .070(2) .060(2) -.007(2) -.017(2) -.0010(17) C11 .0487(19) .056(2) .0591(19) .0044(15) -.0121(17) .0053(16) C12 .0470(18) .0414(17) .0532(17) .0042(15) .0014(16) .0022(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C3 O1 H1A 113(2) yes C8 N1 C7 120.3(2) yes C8 N1 H1B 120(2) yes C7 N1 H1B 112(2) yes C9 N2 C10 117.5(3) yes C2 C1 C6 121.6(2) ? C2 C1 H1C 119.2 ? C6 C1 H1C 119.2 ? C1 C2 C3 120.5(3) ? C1 C2 H2B 119.8 ? C3 C2 H2B 119.8 ? O1 C3 C4 122.2(2) ? O1 C3 C2 118.7(2) ? C4 C3 C2 119.1(3) ? C3 C4 C5 119.9(2) ? C3 C4 H4A 120.1 ? C5 C4 H4A 120.1 ? C6 C5 C4 121.6(3) ? C6 C5 H5A 119.2 ? C4 C5 H5A 119.2 ? C5 C6 C1 117.2(3) ? C5 C6 C7 120.8(2) ? C1 C6 C7 122.0(2) ? N1 C7 C6 112.4(2) ? N1 C7 H7A 109.1 ? C6 C7 H7A 109.1 ? N1 C7 H7B 109.1 ? C6 C7 H7B 109.1 ? H7A C7 H7B 107.9 ? N1 C8 C12 123.9(2) ? N1 C8 C9 120.5(3) ? C12 C8 C9 115.6(2) ? N2 C9 C8 124.6(3) ? N2 C9 H9A 117.7 ? C8 C9 H9A 117.7 ? N2 C10 C11 122.5(3) ? N2 C10 H10A 118.7 ? C11 C10 H10A 118.7 ? C10 C11 C12 119.4(3) ? C10 C11 H11A 120.3 ? C12 C11 H11A 120.3 ? C11 C12 C8 120.3(3) ? C11 C12 H12A 119.8 ? C8 C12 H12A 119.8 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C3 1.363(3) yes O1 H1A .98(4) ? N1 C8 1.368(3) yes N1 C7 1.453(3) yes N1 H1B .89(3) ? N2 C9 1.322(3) yes N2 C10 1.351(4) yes C1 C2 1.376(4) ? C1 C6 1.392(4) ? C1 H1C .9300 ? C2 C3 1.383(4) ? C2 H2B .9300 ? C3 C4 1.382(4) ? C4 C5 1.390(4) ? C4 H4A .9300 ? C5 C6 1.388(3) ? C5 H5A .9300 ? C6 C7 1.504(4) ? C7 H7A .9700 ? C7 H7B .9700 ? C8 C12 1.398(4) ? C8 C9 1.401(4) ? C9 H9A .9300 ? C10 C11 1.363(4) ? C10 H10A .9300 ? C11 C12 1.367(4) ? C11 H11A .9300 ? C12 H12A .9300 ? 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 N2 2_554 .98(4) 1.75(4) 2.723(3) 170(4) yes N1 H1B O1 3_555 .89(3) 2.26(3) 3.133(3) 166(3) yes 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 C6 C1 C2 C3 -.8(4) C1 C2 C3 O1 -178.2(2) C1 C2 C3 C4 3.0(4) O1 C3 C4 C5 179.0(2) C2 C3 C4 C5 -2.3(4) C3 C4 C5 C6 -.7(4) C4 C5 C6 C1 2.9(4) C4 C5 C6 C7 -179.0(2) C2 C1 C6 C5 -2.2(4) C2 C1 C6 C7 179.8(2) C8 N1 C7 C6 174.1(2) C5 C6 C7 N1 128.7(3) C1 C6 C7 N1 -53.4(3) C7 N1 C8 C12 -8.6(4) C7 N1 C8 C9 171.6(3) C10 N2 C9 C8 .2(4) N1 C8 C9 N2 178.0(3) C12 C8 C9 N2 -1.7(4) C9 N2 C10 C11 .6(5) N2 C10 C11 C12 .2(5) C10 C11 C12 C8 -1.8(4) N1 C8 C12 C11 -177.3(3) C9 C8 C12 C11 2.5(4)