##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'form.cif'
_journal_date_recd_electronic     2001-04-18
_journal_date_accepted     2001-04-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue      5
_journal_page_first     o454
_journal_page_last     o455
_journal_paper_category     EO
_publ_contact_author_name     'Sema Ozturk'
_publ_contact_author_address
;
Department of Physics
Faculty of Arts and Sciences
Erciyes University
38039 Kayseri
Turkey
;
_publ_contact_author_email     ozturk@erciyes.edu.tr
_publ_contact_author_fax     '+90-352-4374933'
_publ_contact_author_phone     '+90-352-4374901 extra 33118'
_publ_section_title
;
4,6-Dimethyl-2-(o-tolyliminomethyl)quinoline
;
loop_
    _publ_author_name
    _publ_author_address
    'Mehmet Akkurt'
;     Department of Physics
      Faculty of Arts and Sciences
      Erciyes University, 38039 Kayseri
      Turkey
;
    'Sema Öztürk'
;     Department of Physics
      Faculty of Arts and Sciences
      Erciyes University, 38039 Kayseri
      Turkey
;
; Muhíttín Aygün
;
;     Department of Physics
      Faculty of Arts and Sciences
      Dokuz Eylül University, 33150, Buca Ízmir
      Turkey
;
    'Feray Aydog̃an'
;     Department of Chemistry
      Faculty of Arts and Sciences
      Yıldız Technical University, 80270 Ístanbul
      Turkey
;
data_I
_audit_creation_method     SHELXL
_chemical_name_systematic
;
4,6-Dimethyl-2-(o-tolyliminomethyl)quinoline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H18 N2'
_chemical_formula_sum     'C19 H18 N2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C19 H18 N2'
_chemical_formula_weight     274.37
_chemical_melting_point     ?
_symmetry_cell_setting     'triclinic'
_symmetry_space_group_name_H-M     'P -1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.5693(7)
_cell_length_b     9.5620(9)
_cell_length_c     11.3908(11)
_cell_angle_alpha     79.203(2)
_cell_angle_beta     76.735(2)
_cell_angle_gamma     77.514(2)
_cell_volume     775.19(13)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1739
_cell_measurement_theta_min     3.05
_cell_measurement_theta_max     27.49
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max      .44
_exptl_crystal_size_mid      .26
_exptl_crystal_size_min      .06
_exptl_crystal_density_diffrn     1.180
_exptl_crystal_density_meas     none
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     294
_exptl_absorpt_coefficient_mu      .070
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device     'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_reflns_number     5000
_diffrn_reflns_av_R_equivalents      .0349
_diffrn_reflns_av_sigmaI/netI      .0760
_diffrn_reflns_theta_min     3.05
_diffrn_reflns_theta_max     27.49
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement on F² for ALL reflections except for 0 with very negative F²
 or flagged by the user for potential systematic errors.  Weighted R-factors
 wR and all goodnesses of fit S are based on F², conventional R-factors R
 are based on F, with F set to zero for negative F². The observed criterion
 of F² > 2sigma(F²) is used only for calculating R-factor-obs etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3414
_reflns_number_observed     1697
_reflns_observed_criterion     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .1446
_refine_ls_R_factor_obs      .0731
_refine_ls_wR_factor_all      .2363
_refine_ls_wR_factor_obs      .1868
_refine_ls_goodness_of_fit_all     1.018
_refine_ls_goodness_of_fit_obs     1.162
_refine_ls_restrained_S_all     1.018
_refine_ls_restrained_S_obs     1.162
_refine_ls_number_reflns     3414
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.1124P)²+0.0410P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/esd_max     <0.001
_refine_ls_shift/esd_mean      .000
_refine_diff_density_max      .243
_refine_diff_density_min      -.269
_refine_ls_extinction_method     SHELXL93
_refine_ls_extinction_coef      .023(9)
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'
_computing_data_collection     'SMART (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS86 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL93 (Sheldrick, 1993)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     ?
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_disorder_group
    _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_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)
_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_site_symmetry_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_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_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_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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_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) ?
