##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-2-[(4-Fluorophenyl)iminomethyl]-5-methoxyphenol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H12 F N O2'
_chemical_formula_sum     'C14 H12 F N O2'
_chemical_formula_iupac     'C14 H12 F N O2'
_chemical_formula_weight     245.25
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P c'
_symmetry_space_group_name_Hall     'P -2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x, -y, z+1/2'
_cell_length_a     13.1806(7)
_cell_length_b     7.1785(5)
_cell_length_c     6.4297(3)
_cell_angle_alpha     90.00
_cell_angle_beta     97.967(4)
_cell_angle_gamma     90.00
_cell_volume     602.49(6)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     11108
_cell_measurement_theta_min     1.56
_cell_measurement_theta_max     27.96
_cell_measurement_temperature     296
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.680
_exptl_crystal_size_mid     0.477
_exptl_crystal_size_min     0.170
_exptl_crystal_density_diffrn     1.352
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     256
_exptl_absorpt_coefficient_mu     0.101
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details     '(X-RED32; Stoe & Cie, 2002)'
_exptl_absorpt_correction_T_min     0.9322
_exptl_absorpt_correction_T_max     0.9847
_exptl_special_details
;
237 frames, detector distance = 100 mm
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'plane graphite'
_diffrn_measurement_device_type     'Stoe IPDS II'
_diffrn_measurement_method     'ω-scan rotation method'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     6287
_diffrn_reflns_av_R_equivalents     0.0374
_diffrn_reflns_av_sigmaI/netI     0.0258
_diffrn_reflns_theta_min     2.84
_diffrn_reflns_theta_max     27.55
_diffrn_reflns_theta_full     27.55
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     8
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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     1399
_reflns_number_gt     1273
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0380
_refine_ls_R_factor_gt     0.0349
_refine_ls_wR_factor_gt     0.1017
_refine_ls_wR_factor_ref     0.1037
_refine_ls_goodness_of_fit_ref     1.085
_refine_ls_restrained_S_all     1.084
_refine_ls_number_reflns     1399
_refine_ls_number_parameters     168
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0672P)²+0.0142P] 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     0.200
_refine_diff_density_min     -0.110
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.022(7)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'F' 'F' 0.0171 0.0103
                         '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     'SHELXS97 (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 0.67815(17) 0.7844(3) 0.5679(3) 0.0430(5) Uani d . 1 . .
    C C2 0.68722(16) 0.7118(3) 0.3666(3) 0.0452(5) Uani d . 1 . .
    C C3 0.78232(18) 0.6912(3) 0.3009(4) 0.0473(5) Uani d . 1 . .
    H H3 0.7878 0.6379 0.1711 0.057 Uiso calc R 1 . .
    C C4 0.86907(16) 0.7504(3) 0.4299(3) 0.0448(5) Uani d . 1 . .
    C C5 0.86142(16) 0.8247(3) 0.6292(3) 0.0482(5) Uani d . 1 . .
    H H5 0.9199 0.8648 0.7153 0.058 Uiso calc R 1 . .
    C C6 0.76785(16) 0.8378(3) 0.6958(3) 0.0472(5) Uani d . 1 . .
    H H6 0.7637 0.8834 0.8297 0.057 Uiso calc R 1 . .
    C C7 0.9809(2) 0.6644(5) 0.1854(5) 0.0735(7) Uani d . 1 . .
    H H7A 0.9579 0.5374 0.1792 0.088 Uiso calc R 1 . .
    H H7B 1.0525 0.6683 0.1720 0.088 Uiso calc R 1 . .
    H H7C 0.9429 0.7339 0.0730 0.088 Uiso calc R 1 . .
    C C8 0.58033(17) 0.7980(3) 0.6444(3) 0.0465(5) Uani d . 1 . .
    H H8 0.5785 0.8356 0.7822 0.056 Uiso calc R 1 . .
    C C9 0.40316(17) 0.7582(3) 0.6157(4) 0.0456(5) Uani d . 1 . .
    C C10 0.39603(19) 0.6839(3) 0.8123(4) 0.0539(5) Uani d . 1 . .
    H H10 0.4544 0.6382 0.8942 0.065 Uiso calc R 1 . .
    C C11 0.3028(2) 0.6775(4) 0.8871(4) 0.0606(6) Uani d . 1 . .
    H H11 0.2976 0.6270 1.0184 0.073 Uiso calc R 1 . .
    C C12 0.21810(19) 0.7470(4) 0.7637(5) 0.0598(6) Uani d . 1 . .
    C C13 0.22135(19) 0.8207(4) 0.5678(4) 0.0607(6) Uani d . 1 . .
    H H13 0.1625 0.8667 0.4877 0.073 Uiso calc R 1 . .
    C C14 0.31454(17) 0.8245(4) 0.4932(4) 0.0522(5) Uani d . 1 . .
    H H14 0.3185 0.8717 0.3599 0.063 Uiso calc R 1 . .
    N N1 0.49593(14) 0.7598(2) 0.5277(3) 0.0485(5) Uani d . 1 . .
    O O1 0.60343(14) 0.6613(3) 0.2332(3) 0.0631(5) Uani d D 1 . .
    O O2 0.96531(13) 0.7433(3) 0.3800(3) 0.0561(4) Uani d . 1 . .
    F F1 0.12629(15) 0.7419(3) 0.8381(4) 0.0922(6) Uani d . 1 . .
    H H1 0.553(2) 0.676(4) 0.294(5) 0.079(10) Uiso d 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 0.0418(10) 0.0416(11) 0.0453(12) -0.0015(8) 0.0053(8) -0.0006(8)
    C2 0.0420(11) 0.0492(11) 0.0433(12) -0.0009(8) 0.0020(9) -0.0016(8)
    C3 0.0479(11) 0.0539(12) 0.0406(10) -0.0011(9) 0.0075(8) -0.0044(9)
    C4 0.0433(11) 0.0459(10) 0.0459(12) 0.0014(8) 0.0083(9) 0.0045(9)
    C5 0.0439(11) 0.0547(11) 0.0443(11) -0.0041(8) -0.0003(9) -0.0031(9)
    C6 0.0493(12) 0.0510(11) 0.0403(11) -0.0007(8) 0.0034(9) -0.0047(8)
    C7 0.0540(14) 0.109(2) 0.0612(15) -0.0001(14) 0.0216(11) -0.0148(14)
    C8 0.0456(11) 0.0472(11) 0.0467(11) 0.0012(8) 0.0068(9) -0.0022(8)
    C9 0.0427(11) 0.0453(11) 0.0492(12) -0.0012(8) 0.0073(9) -0.0028(8)
    C10 0.0521(12) 0.0561(12) 0.0527(13) 0.0052(10) 0.0051(10) 0.0028(10)
    C11 0.0668(16) 0.0630(13) 0.0541(13) -0.0032(12) 0.0158(12) 0.0027(11)
    C12 0.0453(13) 0.0678(14) 0.0692(17) -0.0077(10) 0.0184(12) -0.0090(12)
    C13 0.0435(12) 0.0705(15) 0.0663(17) -0.0007(11) 0.0008(11) -0.0035(12)
    C14 0.0461(12) 0.0593(12) 0.0503(13) -0.0003(9) 0.0041(9) 0.0013(10)
    N1 0.0415(10) 0.0532(10) 0.0509(11) 0.0016(8) 0.0063(8) -0.0004(8)
    O1 0.0438(8) 0.0922(12) 0.0515(9) -0.0082(8) 0.0007(7) -0.0194(9)
    O2 0.0420(8) 0.0746(12) 0.0529(9) -0.0021(7) 0.0108(7) -0.0033(8)
    F1 0.0568(10) 0.1257(16) 0.1005(15) -0.0092(10) 0.0334(9) -0.0025(11)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 . 1.397(3) ?
    C1 C2 . 1.416(3) ?
    C1 C8 . 1.445(3) ?
    C2 O1 . 1.351(3) ?
    C2 C3 . 1.385(3) ?
    C3 C4 . 1.383(3) ?
    C3 H3 . 0.9300 ?
    C4 O2 . 1.352(3) ?
    C4 C5 . 1.404(3) ?
    C5 C6 . 1.364(3) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 O2 . 1.414(3) ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C8 N1 . 1.282(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.387(3) ?
    C9 C14 . 1.399(3) ?
    C9 N1 . 1.417(3) ?
    C10 C11 . 1.381(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.371(4) ?
    C11 H11 . 0.9300 ?
    C12 F1 . 1.362(3) ?
    C12 C13 . 1.372(4) ?
    C13 C14 . 1.379(3) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    O1 H1 . 0.824(19) ?
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 . . 117.86(19) ?
    C6 C1 C8 . . 120.22(19) ?
    C2 C1 C8 . . 121.89(18) ?
    O1 C2 C3 . . 118.2(2) ?
    O1 C2 C1 . . 120.96(19) ?
    C3 C2 C1 . . 120.86(18) ?
    C4 C3 C2 . . 119.5(2) ?
    C4 C3 H3 . . 120.3 ?
    C2 C3 H3 . . 120.3 ?
    O2 C4 C3 . . 124.8(2) ?
    O2 C4 C5 . . 114.78(19) ?
    C3 C4 C5 . . 120.4(2) ?
    C6 C5 C4 . . 119.69(19) ?
    C6 C5 H5 . . 120.2 ?
    C4 C5 H5 . . 120.2 ?
    C5 C6 C1 . . 121.6(2) ?
    C5 C6 H6 . . 119.2 ?
    C1 C6 H6 . . 119.2 ?
    O2 C7 H7A . . 109.5 ?
    O2 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    O2 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    N1 C8 C1 . . 121.93(19) ?
    N1 C8 H8 . . 119.0 ?
    C1 C8 H8 . . 119.0 ?
    C10 C9 C14 . . 119.1(2) ?
    C10 C9 N1 . . 122.6(2) ?
    C14 C9 N1 . . 118.2(2) ?
    C11 C10 C9 . . 120.4(2) ?
    C11 C10 H10 . . 119.8 ?
    C9 C10 H10 . . 119.8 ?
    C12 C11 C10 . . 118.6(3) ?
    C12 C11 H11 . . 120.7 ?
    C10 C11 H11 . . 120.7 ?
    F1 C12 C11 . . 118.6(3) ?
    F1 C12 C13 . . 118.4(3) ?
    C11 C12 C13 . . 123.0(2) ?
    C12 C13 C14 . . 118.0(2) ?
    C12 C13 H13 . . 121.0 ?
    C14 C13 H13 . . 121.0 ?
    C13 C14 C9 . . 120.8(2) ?
    C13 C14 H14 . . 119.6 ?
    C9 C14 H14 . . 119.6 ?
    C8 N1 C9 . . 119.66(17) ?
    C2 O1 H1 . . 108(3) ?
    C4 O2 C7 . . 118.77(19) ?
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 O1 . . . . -178.6(2) ?
    C8 C1 C2 O1 . . . . 3.5(3) ?
    C6 C1 C2 C3 . . . . 1.3(3) ?
    C8 C1 C2 C3 . . . . -176.6(2) ?
    O1 C2 C3 C4 . . . . 176.8(2) ?
    C1 C2 C3 C4 . . . . -3.1(3) ?
    C2 C3 C4 O2 . . . . -177.68(19) ?
    C2 C3 C4 C5 . . . . 2.3(3) ?
    O2 C4 C5 C6 . . . . -179.79(19) ?
    C3 C4 C5 C6 . . . . 0.2(3) ?
    C4 C5 C6 C1 . . . . -2.1(3) ?
    C2 C1 C6 C5 . . . . 1.3(3) ?
    C8 C1 C6 C5 . . . . 179.26(19) ?
    C6 C1 C8 N1 . . . . 176.2(2) ?
    C2 C1 C8 N1 . . . . -5.9(3) ?
    C14 C9 C10 C11 . . . . -0.7(3) ?
    N1 C9 C10 C11 . . . . -176.9(2) ?
    C9 C10 C11 C12 . . . . -0.4(4) ?
    C10 C11 C12 F1 . . . . -179.5(2) ?
    C10 C11 C12 C13 . . . . 0.9(4) ?
    F1 C12 C13 C14 . . . . -179.7(2) ?
    C11 C12 C13 C14 . . . . -0.1(4) ?
    C12 C13 C14 C9 . . . . -1.1(4) ?
    C10 C9 C14 C13 . . . . 1.5(3) ?
    N1 C9 C14 C13 . . . . 177.9(2) ?
    C1 C8 N1 C9 . . . . 174.01(17) ?
    C10 C9 N1 C8 . . . . -40.8(3) ?
    C14 C9 N1 C8 . . . . 143.0(2) ?
    C3 C4 O2 C7 . . . . -2.2(3) ?
    C5 C4 O2 C7 . . . . 177.8(2) ?
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 H1 N1 . 0.824(19) 1.87(2) 2.615(3) 150(3)
    C6 H6 Cg1 2_555 0.93 2.73 3.4363 133.00
    C11 H11 Cg2 2_565 0.93 2.93 3.6414 134.00
    C14 H14 Cg2 2_554 0.93 2.91 3.6076 133.00
data_global
_journal_date_recd_electronic     2010-01-04
_journal_date_accepted     2010-01-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      2
_journal_page_first     o315
_journal_page_last     o315
_journal_paper_category     QO
_journal_coeditor_code     BT5163
_publ_contact_author_name     'Albayrak, Çiğdem'
_publ_contact_author_address
;
Faculty of Education,
Sinop University,
Sinop
Turkey
;
_publ_contact_author_email     'calbayrak@sinop.edu.tr'
_publ_section_title
;
(E)-2-[(4-Fluorophenyl)iminomethyl]-5-methoxyphenol
;
loop_
    _publ_author_name
    _publ_author_address
    'Albayrak, Çiğdem'
;
Faculty of Education,
Sinop University,
Sinop
Turkey
;
    'Özek, Arzu'
;
Department of Physics,
Ondokuz Mayıs University,
TR-55139 Samsun
Turkey
;
    'Koşar, Başak'
;
Faculty of Education,
Sinop University,
Sinop
Turkey
;
    'Odabaşoğlu, Mustafa'
;
Chemistry Programme
Denizli Higher Vocational School,
Pamukkale University
TR-20159 Denizli
Turkey
;
    'Büyükgüngör, Orhan'
;
Department of Physics,
Ondokuz Mayıs University,
TR-55139 Samsun
Turkey
;
