#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2200273.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_2200273 loop_ _publ_author_name 'Akkurt, Mehmet' '\"Ozt\"urk, Sema' 'Ayg\"un, Muh\'itt\'in' 'Aydogan, Feray' _publ_section_title ; 4,6-Dimethyl-2-(o-tolyliminomethyl)quinoline ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o454 _journal_page_last o455 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C19 H18 N2' _chemical_formula_moiety 'C19 H18 N2' _chemical_formula_sum 'C19 H18 N2' _chemical_formula_weight 274.37 _chemical_name_systematic ; 4,6-Dimethyl-2-(o-tolyliminomethyl)quinoline ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL _cell_angle_alpha 79.203(2) _cell_angle_beta 76.735(2) _cell_angle_gamma 77.514(2) _cell_formula_units_Z 2 _cell_length_a 7.5693(7) _cell_length_b 9.5620(9) _cell_length_c 11.3908(11) _cell_measurement_reflns_used 1739 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.49 _cell_measurement_theta_min 3.05 _cell_volume 775.19(13) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Siemens SMART 1000 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 .0349 _diffrn_reflns_av_sigmaI/netI .0760 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 5000 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 3.05 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .070 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_meas none _exptl_crystal_description needle _exptl_crystal_F_000 294 _exptl_crystal_size_max .44 _exptl_crystal_size_mid .26 _exptl_crystal_size_min .06 _refine_diff_density_max .243 _refine_diff_density_min -.269 _refine_ls_extinction_coef .023(9) _refine_ls_extinction_method SHELXL93 _refine_ls_goodness_of_fit_all 1.018 _refine_ls_goodness_of_fit_obs 1.162 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 194 _refine_ls_number_reflns 3414 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_restrained_S_obs 1.162 _refine_ls_R_factor_all .1446 _refine_ls_R_factor_obs .0731 _refine_ls_shift/esd_max <0.001 _refine_ls_shift/esd_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1124P)^2^+0.0410P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .2363 _refine_ls_wR_factor_obs .1868 _reflns_number_observed 1697 _reflns_number_total 3414 _reflns_observed_criterion I>2\s(I) _[local]_cod_data_source_file bt6038.cif _[local]_cod_data_source_block I _cod_database_code 2200273 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 .061(2) .0579(14) .0441(12) -.0158(11) -.0143(10) -.0078(11) N2 .061(2) .0510(13) .0520(13) -.0140(11) -.0165(11) .0016(11) C1 .052(2) .049(2) .053(2) -.0121(12) -.0143(13) -.0062(13) C2 .062(2) .0454(15) .057(2) -.0178(13) -.0171(13) -.0053(14) C3 .052(2) .051(2) .052(2) -.0145(12) -.0133(12) -.0064(13) C4 .0426(15) .0440(14) .053(2) -.0101(11) -.0101(12) -.0041(13) C5 .059(2) .050(2) .059(2) -.0092(13) -.0149(14) .0000(14) C6 .056(2) .045(2) .075(2) -.0076(13) -.0081(15) -.0040(15) C7 .065(2) .045(2) .085(2) -.0112(14) -.011(2) -.017(2) C8 .061(2) .057(2) .064(2) -.0143(14) -.0119(14) -.017(2) C9 .046(2) .0477(15) .056(2) -.0100(12) -.0100(12) -.0080(13) C10 .088(2) .057(2) .056(2) -.021(2) -.024(2) -.0058(15) C11 .086(3) .050(2) .105(3) -.010(2) -.017(2) .005(2) C12 .063(2) .058(2) .049(2) -.0120(14) -.0172(13) -.0045(14) C13 .064(2) .0474(15) .0455(15) -.0115(13) -.0170(13) -.0036(13) C14 .074(2) .066(2) .074(2) -.017(2) -.031(2) .002(2) C15 .100(3) .074(2) .087(2) -.007(2) -.050(2) .009(2) C16 .126(3) .062(2) .061(2) -.013(2) -.028(2) .014(2) C17 .094(3) .064(2) .057(2) -.026(2) -.007(2) -.001(2) C18 .067(2) .053(2) .0457(15) -.0158(14) -.0092(13) -.0050(13) C19 .068(2) .093(2) .074(2) -.025(2) -.016(2) -.006(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol N1 .2160(3) .1467(2) .2710(2) .0529(6) Uani d . 1 N N2 .2614(3) .5139(2) .2097(2) .0544(6) Uani d . 1 N C1 .2282(4) .2707(3) .2999(2) .0504(7) Uani d . 1 C C2 .2442(4) .2870(3) .4167(2) .0531(7) Uani d . 1 C H2B .2493 .3779 .4326 .064 Uiso calc R 1 H C3 .2524(4) .1713(3) .5074(2) .0504(7) Uani d . 1 C C4 .2448(3) .0344(3) .4775(2) .0463(6) Uani d . 1 C C5 .2588(4) -.0961(3) .5607(3) .0566(7) Uani d . 1 C H5A .2738 -.0940 .6391 .068 Uiso calc R 1 H C6 .2507(4) -.2254(3) .5284(3) .0604(8) Uani d . 1 C C7 .2279(4) -.2278(3) .4103(3) .0641(8) Uani d . 1 C H7A .2215 -.3151 .3882 .077 Uiso calc R 1 H C8 .2148(4) -.1058(3) .3274(3) .0594(8) Uani d . 1 C H8A .1982 -.1103 .2499 .071 Uiso calc R 1 H C9 .2263(4) .0276(3) .3581(2) .0494(7) Uani d . 1 C C10 .2665(5) .1883(3) .6327(3) .0649(9) Uani d . 1 C H10A .3793 .1303 .6522 .097 Uiso calc R 1 H H10B .1635 .1573 .6907 .097 Uiso calc R 1 H H10C .2657 .2881 .6356 .097 Uiso calc R 1 H C11 .2706(5) -.3633(3) .6187(4) .0832(11) Uani d . 1 C H11A .1772 -.4169 .6183 .125 Uiso calc R 1 H H11B .2569 -.3394 .6989 .125 Uiso calc R 1 H H11C .3903 -.4209 .5961 .125 Uiso calc R 1 H C12 .2241(4) .3936(3) .2010(3) .0556(7) Uani d . 1 C H12A .1930 .3828 .1293 .067 Uiso calc R 1 H C13 .2501(4) .6284(3) .1108(2) .0514(7) Uani d . 1 C C14 .0932(5) .6723(3) .0603(3) .0696(9) Uani d . 1 C H14A -.0047 .6224 .0885 .083 Uiso calc R 1 H C15 .0804(6) .7884(4) -.0307(3) .0859(11) Uani d . 1 C H15A -.0250 .8171 -.0642 .103 Uiso calc R 1 H C16 .2257(6) .8616(4) -.0716(3) .0853(12) Uani d . 1 C H16A .2185 .9401 -.1334 .102 Uiso calc R 1 H C17 .3818(5) .8196(3) -.0218(3) .0724(9) Uani d . 1 C H17A .4786 .8705 -.0504 .087 Uiso calc R 1 H C18 .3972(4) .7027(3) .0705(2) .0549(7) Uani d . 1 C C19 .5668(5) .6568(4) .1253(3) .0773(10) Uani d . 1 C H19A .6451 .7278 .0960 .116 Uiso calc R 1 H H19B .6322 .5650 .1024 .116 Uiso calc R 1 H H19C .5317 .6483 .2125 .116 Uiso calc R 1 H 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' 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 C9 118.0(2) yes C12 N2 C13 119.0(2) yes N1 C1 C2 123.2(3) ? N1 C1 C12 115.5(2) ? C2 C1 C12 121.3(2) ? C3 C2 C1 120.9(2) ? C3 C2 H2B 119.6(2) ? C1 C2 H2B 119.6(2) ? C2 C3 C4 117.0(2) ? C2 C3 C10 121.2(2) yes C4 C3 C10 121.8(2) yes C9 C4 C5 118.1(2) ? C9 C4 C3 118.5(2) ? C5 C4 C3 123.4(2) yes C6 C5 C4 121.6(3) ? C6 C5 H5A 119.2(2) ? C4 C5 H5A 119.2(2) ? C5 C6 C7 118.9(3) ? C5 C6 C11 120.2(3) yes C7 C6 C11 120.9(3) yes C8 C7 C6 121.6(3) ? C8 C7 H7A 119.2(2) ? C6 C7 H7A 119.2(2) ? C7 C8 C9 120.3(3) ? C7 C8 H8A 119.8(2) ? C9 C8 H8A 119.8(2) ? N1 C9 C8 118.2(2) yes N1 C9 C4 122.3(2) ? C8 C9 C4 119.5(3) ? C3 C10 H10A 109.5(2) ? C3 C10 H10B 109.5(2) ? H10A C10 H10B 109.5 ? C3 C10 H10C 109.5(2) ? H10A C10 H10C 109.5 ? H10B C10 H10C 109.5 ? C6 C11 H11A 109.5(2) ? C6 C11 H11B 109.5(2) ? H11A C11 H11B 109.5 ? C6 C11 H11C 109.5(2) ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? N2 C12 C1 122.5(3) ? N2 C12 H12A 118.7(2) ? C1 C12 H12A 118.7(2) ? C14 C13 C18 120.3(3) ? C14 C13 N2 121.6(3) ? C18 C13 N2 118.0(2) ? C15 C14 C13 120.8(3) ? C15 C14 H14A 119.6(2) ? C13 C14 H14A 119.6(2) ? C14 C15 C16 119.1(3) ? C14 C15 H15A 120.4(2) ? C16 C15 H15A 120.4(2) ? C15 C16 C17 120.6(3) ? C15 C16 H16A 119.7(2) ? C17 C16 H16A 119.7(2) ? C16 C17 C18 121.2(3) ? C16 C17 H17A 119.4(2) ? C18 C17 H17A 119.4(2) ? C17 C18 C13 117.9(3) ? C17 C18 C19 121.3(3) yes C13 C18 C19 120.7(3) yes C18 C19 H19A 109.5(2) ? C18 C19 H19B 109.5(2) ? H19A C19 H19B 109.5 ? C18 C19 H19C 109.5(2) ? H19A C19 H19C 109.5 ? H19B C19 H19C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C1 1.316(3) yes N1 C9 1.364(3) yes N2 C12 1.267(3) yes N2 C13 1.420(3) yes C1 C2 1.403(4) ? C1 C12 1.468(4) ? C2 C3 1.366(3) ? C2 H2B .93 ? C3 C4 1.429(3) ? C3 C10 1.496(4) yes C4 C9 1.413(4) ? C4 C5 1.419(3) ? C5 C6 1.371(4) ? C5 H5A .93 ? C6 C7 1.400(4) ? C6 C11 1.515(4) yes C7 C8 1.357(4) ? C7 H7A .93 ? C8 C9 1.410(4) ? C8 H8A .93 ? C10 H10A .96 ? C10 H10B .96 ? C10 H10C .96 ? C11 H11A .96 ? C11 H11B .96 ? C11 H11C .96 ? C12 H12A .93 ? C13 C14 1.388(4) ? C13 C18 1.393(4) ? C14 C15 1.373(4) ? C14 H14A .93 ? C15 C16 1.376(5) ? C15 H15A .93 ? C16 C17 1.377(5) ? C16 H16A .93 ? C17 C18 1.388(4) ? C17 H17A .93 ? C18 C19 1.501(4) yes C19 H19A .96 ? C19 H19B .96 ? C19 H19C .96 ? 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 C9 N1 C1 C2 -2.5(4) ? C9 N1 C1 C12 177.5(2) ? N1 C1 C2 C3 1.6(4) ? C12 C1 C2 C3 -178.4(3) ? C1 C2 C3 C4 .3(4) ? C1 C2 C3 C10 -179.1(3) ? C2 C3 C4 C9 -1.1(4) ? C10 C3 C4 C9 178.3(3) ? C2 C3 C4 C5 177.5(3) ? C10 C3 C4 C5 -3.1(4) ? C9 C4 C5 C6 -1.4(4) ? C3 C4 C5 C6 179.9(3) ? C4 C5 C6 C7 -.1(4) ? C4 C5 C6 C11 178.5(3) ? C5 C6 C7 C8 .4(5) ? C11 C6 C7 C8 -178.2(3) ? C6 C7 C8 C9 .8(5) ? C1 N1 C9 C8 -179.5(2) ? C1 N1 C9 C4 1.6(4) ? C7 C8 C9 N1 178.7(3) ? C7 C8 C9 C4 -2.3(4) ? C5 C4 C9 N1 -178.5(2) ? C3 C4 C9 N1 .2(4) ? C5 C4 C9 C8 2.6(4) ? C3 C4 C9 C8 -178.7(2) ? C13 N2 C12 C1 -178.6(2) yes N1 C1 C12 N2 -169.4(3) ? C2 C1 C12 N2 10.6(4) ? C12 N2 C13 C14 52.1(4) ? C12 N2 C13 C18 -132.1(3) ? C18 C13 C14 C15 .6(5) ? N2 C13 C14 C15 176.3(3) ? C13 C14 C15 C16 -.1(5) ? C14 C15 C16 C17 -.3(5) ? C15 C16 C17 C18 .2(5) ? C16 C17 C18 C13 .3(4) ? C16 C17 C18 C19 -179.8(3) ? C14 C13 C18 C17 -.7(4) ? N2 C13 C18 C17 -176.6(3) ? C14 C13 C18 C19 179.4(3) ? N2 C13 C18 C19 3.6(4) ?