##############################################################################
###                                                                        ###
###        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                                                              #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-2-[(2-Chlorophenyl)iminomethyl]-4-methylphenol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H12 Cl N O'
_chemical_formula_sum     'C14 H12 Cl N O'
_chemical_formula_iupac     'C14 H12 Cl N O'
_chemical_formula_weight     245.70
_chemical_melting_point     '356-358'
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_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'
    '-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     7.5121(7)
_cell_length_b     11.9190(15)
_cell_length_c     27.500(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2462.3(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     5622
_cell_measurement_theta_min     27.1
_cell_measurement_theta_max     2.22
_cell_measurement_temperature     296(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.8
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.325
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1024
_exptl_absorpt_coefficient_mu     0.292
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Stoe IPDS-2'
_diffrn_measurement_method     'rotation method'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     14292
_diffrn_reflns_av_R_equivalents     0.1329
_diffrn_reflns_av_sigmaI/netI     0.0850
_diffrn_reflns_theta_min     2.96
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     33
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) 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     2428
_reflns_number_gt     833
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1706
_refine_ls_R_factor_gt     0.0725
_refine_ls_wR_factor_gt     0.1907
_refine_ls_wR_factor_ref     0.2325
_refine_ls_goodness_of_fit_ref     0.814
_refine_ls_restrained_S_all     0.814
_refine_ls_number_reflns     2428
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.1247P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.314
_refine_diff_density_min     -0.339
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0030 0.0020
                         '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'
    'Cl' 'Cl' 0.1480 0.1590
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0060 0.0030
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0110 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction     'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _atom_site_type_symbol
    _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_disorder_assembly
    _atom_site_disorder_group
    C C1 0.0007(7) 0.3349(5) 0.43397(19) 0.0948(15) Uani d . 1 . .
    C C2 -0.0462(6) 0.2701(4) 0.39300(17) 0.0767(12) Uani d . 1 . .
    C C3 -0.0457(7) 0.1562(4) 0.39911(19) 0.0942(15) Uani d . 1 . .
    H H3 -0.0826 0.1102 0.3737 0.113 Uiso calc R 1 . .
    C C4 0.0080(9) 0.1088(5) 0.4419(2) 0.1153(18) Uani d . 1 . .
    H H4 0.0088 0.0310 0.4449 0.138 Uiso calc R 1 . .
    C C5 0.0600(9) 0.1724(6) 0.4798(2) 0.122(2) Uani d . 1 . .
    H H5 0.0990 0.1388 0.5084 0.146 Uiso calc R 1 . .
    C C6 0.0550(9) 0.2868(6) 0.4761(2) 0.1143(19) Uani d . 1 . .
    H H6 0.0888 0.3313 0.5023 0.137 Uiso calc R 1 . .
    C C7 -0.0567(6) 0.2814(4) 0.30913(17) 0.0722(11) Uani d . 1 . .
    C C8 -0.0967(5) 0.3344(4) 0.26359(17) 0.0738(7) Uani d . 1 . .
    C C9 -0.0565(5) 0.2805(4) 0.21962(17) 0.0738(7) Uani d . 1 . .
    C C10 -0.0914(5) 0.3263(3) 0.17485(16) 0.0738(7) Uani d . 1 . .
    C C11 -0.1683(6) 0.4315(4) 0.1750(2) 0.0911(7) Uani d . 1 . .
    H H11 -0.1943 0.4636 0.1450 0.109 Uiso calc R 1 . .
    C C12 -0.2100(6) 0.4931(4) 0.21632(18) 0.0911(7) Uani d . 1 . .
    H H12 -0.2614 0.5639 0.2146 0.109 Uiso calc R 1 . .
    C C13 -0.1696(6) 0.4417(4) 0.2609(2) 0.0911(7) Uani d . 1 . .
    C C14 -0.0490(7) 0.2641(5) 0.12922(18) 0.1075(17) Uani d . 1 . .
    H H15A 0.0380 0.3053 0.1109 0.161 Uiso calc R 1 . .
    H H15B -0.1553 0.2557 0.1102 0.161 Uiso calc R 1 . .
    H H15C -0.0025 0.1914 0.1372 0.161 Uiso calc R 1 . .
    Cl Cl1 -0.0042(3) 0.47953(13) 0.42906(6) 0.1482(9) Uani d . 1 . .
    N N1 -0.0919(5) 0.3258(3) 0.35040(15) 0.0780(10) Uani d . 1 . .
    O O1 -0.2054(4) 0.5014(2) 0.30200(12) 0.0911(7) Uani d . 1 . .
    H H9 -0.1766 0.4645 0.3259 0.137 Uiso calc R 1 . .
    H H1 0.011(5) 0.210(4) 0.3066(13) 0.083(12) Uiso d . 1 . .
    H H2 -0.010(5) 0.211(3) 0.2174(13) 0.072(11) Uiso d . 1 . .
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
    C1 0.093(4) 0.096(3) 0.095(3) -0.001(3) 0.022(3) -0.020(3)
    C2 0.057(3) 0.077(3) 0.096(3) 0.005(2) 0.012(2) -0.006(3)
    C3 0.099(4) 0.080(3) 0.103(4) -0.006(3) -0.007(3) -0.005(3)
    C4 0.145(5) 0.090(4) 0.112(4) -0.003(4) -0.002(4) 0.008(3)
    C5 0.147(6) 0.125(5) 0.093(4) 0.008(5) 0.010(4) 0.005(4)
    C6 0.131(5) 0.120(5) 0.092(4) -0.011(4) 0.010(3) -0.014(4)
    C7 0.053(3) 0.064(3) 0.099(3) -0.001(2) 0.003(2) -0.006(3)
    C8 0.0491(12) 0.0711(17) 0.1013(18) -0.0093(12) -0.0077(14) 0.0037(13)
    C9 0.0491(12) 0.0711(17) 0.1013(18) -0.0093(12) -0.0077(14) 0.0037(13)
    C10 0.0491(12) 0.0711(17) 0.1013(18) -0.0093(12) -0.0077(14) 0.0037(13)
    C11 0.0687(12) 0.0733(13) 0.1313(19) 0.0018(10) 0.0032(12) 0.0041(11)
    C12 0.0687(12) 0.0733(13) 0.1313(19) 0.0018(10) 0.0032(12) 0.0041(11)
    C13 0.0687(12) 0.0733(13) 0.1313(19) 0.0018(10) 0.0032(12) 0.0041(11)
    C14 0.092(4) 0.132(4) 0.098(3) -0.019(3) -0.006(3) -0.015(3)
    Cl1 0.240(2) 0.0908(10) 0.1138(11) -0.0054(12) 0.0417(12) -0.0294(8)
    N1 0.065(2) 0.074(2) 0.095(3) -0.0028(19) 0.016(2) -0.009(2)
    O1 0.0687(12) 0.0733(13) 0.1313(19) 0.0018(10) 0.0032(12) 0.0041(11)
_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
    C1 C6 . 1.354(7) ?
    C1 C2 . 1.410(6) ?
    C1 Cl1 . 1.730(6) ?
    C2 C3 . 1.368(6) ?
    C2 N1 . 1.390(5) ?
    C3 C4 . 1.366(7) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.348(7) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.368(8) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 N1 . 1.280(5) y
    C7 C8 . 1.434(6) ?
    C7 H1 . 0.99(4) ?
    C8 C13 . 1.393(6) ?
    C8 C9 . 1.402(6) ?
    C9 C10 . 1.372(6) ?
    C9 H2 . 0.91(4) ?
    C10 C11 . 1.380(6) ?
    C10 C14 . 1.491(6) ?
    C11 C12 . 1.389(6) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.403(6) ?
    C12 H12 . 0.9300 ?
    C13 O1 . 1.364(6) y
    C14 H15A . 0.9600 ?
    C14 H15B . 0.9600 ?
    C14 H15C . 0.9600 ?
    O1 H9 . 0.8200 ?
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
    C6 C1 C2 . . 121.8(5) ?
    C6 C1 Cl1 . . 119.6(4) ?
    C2 C1 Cl1 . . 118.5(4) ?
    C3 C2 N1 . . 125.3(4) ?
    C3 C2 C1 . . 116.4(5) ?
    N1 C2 C1 . . 118.3(4) ?
    C4 C3 C2 . . 121.2(5) ?
    C4 C3 H3 . . 119.4 ?
    C2 C3 H3 . . 119.4 ?
    C5 C4 C3 . . 121.3(6) ?
    C5 C4 H4 . . 119.4 ?
    C3 C4 H4 . . 119.4 ?
    C4 C5 C6 . . 119.6(6) ?
    C4 C5 H5 . . 120.2 ?
    C6 C5 H5 . . 120.2 ?
    C1 C6 C5 . . 119.6(6) ?
    C1 C6 H6 . . 120.2 ?
    C5 C6 H6 . . 120.2 ?
    N1 C7 C8 . . 123.3(5) ?
    N1 C7 H1 . . 122(2) ?
    C8 C7 H1 . . 115(2) ?
    C13 C8 C9 . . 117.3(5) ?
    C13 C8 C7 . . 122.2(5) ?
    C9 C8 C7 . . 120.4(4) ?
    C10 C9 C8 . . 123.4(5) ?
    C10 C9 H2 . . 112(2) ?
    C8 C9 H2 . . 124(2) ?
    C9 C10 C11 . . 116.0(5) ?
    C9 C10 C14 . . 121.1(4) ?
    C11 C10 C14 . . 122.8(5) ?
    C10 C11 C12 . . 125.2(5) ?
    C10 C11 H11 . . 117.4 ?
    C12 C11 H11 . . 117.4 ?
    C11 C12 C13 . . 115.8(5) ?
    C11 C12 H12 . . 122.1 ?
    C13 C12 H12 . . 122.1 ?
    O1 C13 C8 . . 120.8(5) ?
    O1 C13 C12 . . 117.0(4) ?
    C8 C13 C12 . . 122.2(5) ?
    C10 C14 H15A . . 109.5 ?
    C10 C14 H15B . . 109.5 ?
    H15A C14 H15B . . 109.5 ?
    C10 C14 H15C . . 109.5 ?
    H15A C14 H15C . . 109.5 ?
    H15B C14 H15C . . 109.5 ?
    C7 N1 C2 . . 119.9(4) ?
    C13 O1 H9 . . 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
    C6 C1 C2 C3 . . . . 4.4(7) ?
    Cl1 C1 C2 C3 . . . . -178.0(4) ?
    C6 C1 C2 N1 . . . . -176.8(5) ?
    Cl1 C1 C2 N1 . . . . 0.8(6) ?
    N1 C2 C3 C4 . . . . 177.4(5) ?
    C1 C2 C3 C4 . . . . -3.8(8) ?
    C2 C3 C4 C5 . . . . 1.0(9) ?
    C3 C4 C5 C6 . . . . 1.6(10) ?
    C2 C1 C6 C5 . . . . -2.0(9) ?
    Cl1 C1 C6 C5 . . . . -179.6(5) ?
    C4 C5 C6 C1 . . . . -1.0(10) ?
    N1 C7 C8 C13 . . . . 3.4(6) ?
    N1 C7 C8 C9 . . . . -179.2(4) ?
    C13 C8 C9 C10 . . . . -2.5(6) ?
    C7 C8 C9 C10 . . . . 179.9(4) ?
    C8 C9 C10 C11 . . . . 0.7(6) ?
    C8 C9 C10 C14 . . . . -178.7(4) ?
    C9 C10 C11 C12 . . . . 0.7(7) ?
    C14 C10 C11 C12 . . . . -179.8(4) ?
    C10 C11 C12 C13 . . . . -0.3(7) ?
    C9 C8 C13 O1 . . . . -177.2(4) ?
    C7 C8 C13 O1 . . . . 0.3(6) ?
    C9 C8 C13 C12 . . . . 3.0(6) ?
    C7 C8 C13 C12 . . . . -179.5(4) ?
    C11 C12 C13 O1 . . . . 178.5(4) ?
    C11 C12 C13 C8 . . . . -1.7(7) ?
    C8 C7 N1 C2 . . . . -178.9(4) ?
    C3 C2 N1 C7 . . . . -33.4(6) ?
    C1 C2 N1 C7 . . . . 147.9(4) ?
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
    O1 H9 N1 . 0.82 1.89 2.622(5) 147.3
    C14 H15B Cg1 6_556 0.93 2.831 3.849(6) 173.58
data_global
_journal_date_recd_electronic     2007-12-11
_journal_date_accepted     2007-12-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      2
_journal_page_first     o539
_journal_page_last     o539
_journal_paper_category     QO
_journal_coeditor_code     XU2392
_publ_contact_author
;
        'Deveci, Özlem'
        Department of Physics
        Faculty of Arts & Science
        Ondokuz Mayıs University
        TR-55139
        Kurupelit-Samsun
        Turkey
;
_publ_contact_author_email     odeveci@omu.edu.tr
_publ_section_title
;
(E)-2-[(2-Chlorophenyl)iminomethyl]-4-methylphenol
;
loop_
    _publ_author_name
    _publ_author_address
    'Deveci, Özlem'
;   Department of Physics
    Faculty of Arts & Science
    Ondokuz Mayıs University
    TR-55139 Kurupelit-Samsun
    Turkey
;
    'Işık, Şamil'
;     Department of Physics
      Faculty of Arts & Science
      Ondokuz Mayıs University
      TR-55139 Kurupelit-Samsun
      Turkey
;
    'Erşahin, Ferda'
;    Department of Chemistry
     Faculty of Arts & Science
     Ondokuz Mayıs University
     55139 Samsun
     Turkey
;
    'Ağar, Erbil'
;    Department of Chemistry
     Faculty of Arts & Science
     Ondokuz Mayıs University
     55139 Samsun
     Turkey
;
