##############################################################################
###                                                                        ###
###        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/  #
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#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-02-28
_journal_date_accepted     2006-03-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      5
_journal_page_first     o1699
_journal_page_last     o1701
_journal_paper_category     EO
_journal_coeditor_code     IS2010
_publ_contact_author
;
'Karadayı, Nevzat'
Industrial Electronics Program
Samsun Vocational School
Ondokuz Mayıs University
TR-55139
Samsun
Turkey
;
_publ_contact_author_email     'nevzatk@omu.edu.tr '
_publ_section_title
;
(E)-5-[(3-Chlorophenyl)diazenyl]-2-hydroxy-3-methoxybenzaldehyde
;
loop_
    _publ_author_name
    _publ_author_address
    'Karadayı, Nevzat'
;
Industrial Electronics Program
Samsun Vocational School
Ondokuz Mayıs University
TR-55139 Samsun
Turkey
;
    'Albayrak, Çiğdem'
;
Department of Chemistry
Faculty of Arts and Sciences
Ondokuz Mayıs University
TR-55139 Samsun
Turkey
;
    'Odabaşoğlu, Mustafa '
;
Department of Chemistry
Faculty of Arts and Sciences
Ondokuz Mayıs University
TR-55139 Samsun
Turkey
;
    'Büyükgüngör, Orhan'
;
Department of Physics
Faculty of Arts and Sciences
Ondokuz Mayıs University
TR-55139 Samsun
Turkey
;
data_I
_chemical_name_systematic
;
(E)-5-[(3-Chlorophenyl)diazenyl]-2-hydroxy-3-methoxybenzaldehyde
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 Cl N2 O3'
_chemical_formula_sum     'C14 H11 Cl N2 O3'
_chemical_formula_iupac     'C14 H11 Cl N2 O3'
_chemical_formula_weight     290.70
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c n'
_symmetry_space_group_name_Hall     '-P 2n 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y-1/2, -z-1/2'
    '-x-1/2, y-1/2, z'
    'x, -y, z-1/2'
_cell_length_a     12.3199(15)
_cell_length_b     13.0849(17)
_cell_length_c     16.6349(16)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2681.6(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4559
_cell_measurement_theta_min     2.27
_cell_measurement_theta_max     26.20
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'red'
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.440
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1200
_exptl_absorpt_coefficient_mu     0.293
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details     '(X-RED32; Stoe & Cie, 2002)'
_exptl_absorpt_correction_T_min     0.9160
_exptl_absorpt_correction_T_max     0.9711
_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     'plane graphite'
_diffrn_measurement_device_type     'Stoe IPDS-2'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10851
_diffrn_reflns_av_R_equivalents     0.0546
_diffrn_reflns_av_sigmaI/netI     0.0589
_diffrn_reflns_theta_min     2.27
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     19
_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     2364
_reflns_number_gt     1325
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0760
_refine_ls_R_factor_gt     0.0341
_refine_ls_wR_factor_gt     0.0564
_refine_ls_wR_factor_ref     0.0608
_refine_ls_goodness_of_fit_ref     0.934
_refine_ls_restrained_S_all     0.934
_refine_ls_number_reflns     2364
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0183P)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     0.111
_refine_diff_density_min     -0.158
_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' 0.0033 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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA'
_computing_data_reduction     'X-RED (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                              'ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 2003)'
_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
    Cl Cl1 0.93170(5) 0.61244(5) -0.10140(4) 0.0773(2) Uani d . 1 . .
    O O1 0.40847(12) 0.21442(10) 0.17362(9) 0.0654(4) Uani d . 1 . .
    O O2 0.24710(14) 0.28841(11) 0.25415(9) 0.0737(5) Uani d . 1 . .
    H H1 0.1987 0.3188 0.2781 0.110 Uiso calc R 1 . .
    O O3 0.14321(14) 0.44942(13) 0.30904(10) 0.0832(5) Uani d . 1 . .
    N N1 0.60666(14) 0.53092(11) 0.07392(10) 0.0504(4) Uani d . 1 . .
    N N2 0.52488(14) 0.56508(12) 0.10959(10) 0.0510(4) Uani d . 1 . .
    C C1 0.67461(16) 0.61046(14) 0.04301(11) 0.0452(5) Uani d . 1 . .
    C C2 0.66322(18) 0.71264(14) 0.06210(13) 0.0563(6) Uani d . 1 . .
    H H2 0.6081 0.7339 0.0965 0.068 Uiso calc R 1 . .
    C C3 0.7340(2) 0.78257(16) 0.02984(14) 0.0647(7) Uani d . 1 . .
    H H3 0.7263 0.8513 0.0430 0.078 Uiso calc R 1 . .
    C C4 0.81598(19) 0.75360(16) -0.02141(13) 0.0592(6) Uani d . 1 . .
    H H4 0.8627 0.8018 -0.0435 0.071 Uiso calc R 1 . .
    C C5 0.82701(16) 0.65156(15) -0.03915(12) 0.0506(6) Uani d . 1 . .
    C C6 0.75764(16) 0.58013(15) -0.00712(12) 0.0506(5) Uani d . 1 . .
    H H6 0.7667 0.5113 -0.0193 0.061 Uiso calc R 1 . .
    C C7 0.45547(15) 0.49039(15) 0.14420(12) 0.0464(5) Uani d . 1 . .
    C C8 0.36929(17) 0.52735(15) 0.18711(13) 0.0520(5) Uani d . 1 . .
    H H8 0.3588 0.5976 0.1908 0.062 Uiso calc R 1 . .
    C C9 0.29738(17) 0.46191(16) 0.22524(12) 0.0508(6) Uani d . 1 . .
    C C10 0.31361(17) 0.35680(16) 0.21859(13) 0.0527(6) Uani d . 1 . .
    C C11 0.40128(16) 0.31779(14) 0.17446(13) 0.0491(5) Uani d . 1 . .
    C C12 0.47195(16) 0.38426(15) 0.13782(11) 0.0478(5) Uani d . 1 . .
    H H12 0.5307 0.3591 0.1088 0.057 Uiso calc R 1 . .
    C C13 0.2080(2) 0.50185(19) 0.27189(14) 0.0664(7) Uani d . 1 . .
    H H13 0.1993 0.5724 0.2737 0.080 Uiso calc R 1 . .
    C C14 0.4967(2) 0.17053(16) 0.12979(15) 0.0743(8) Uani d . 1 . .
    H H14A 0.4931 0.0974 0.1335 0.111 Uiso calc R 1 . .
    H H14B 0.5641 0.1939 0.1520 0.111 Uiso calc R 1 . .
    H H14C 0.4921 0.1908 0.0744 0.111 Uiso calc R 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
    Cl1 0.0600(4) 0.0814(4) 0.0905(4) -0.0152(3) 0.0255(4) -0.0147(4)
    O1 0.0681(11) 0.0463(9) 0.0818(11) 0.0037(8) 0.0166(9) 0.0094(8)
    O2 0.0678(11) 0.0668(10) 0.0864(12) -0.0034(9) 0.0291(9) 0.0157(9)
    O3 0.0706(12) 0.0912(12) 0.0877(13) 0.0020(10) 0.0337(11) 0.0043(10)
    N1 0.0462(11) 0.0491(10) 0.0558(12) -0.0040(9) 0.0046(10) 0.0052(9)
    N2 0.0460(11) 0.0514(10) 0.0557(12) -0.0021(9) 0.0043(10) 0.0053(9)
    C1 0.0430(12) 0.0449(12) 0.0478(13) -0.0015(10) -0.0023(10) 0.0046(10)
    C2 0.0576(14) 0.0477(13) 0.0635(15) 0.0011(11) 0.0069(12) 0.0003(11)
    C3 0.0720(17) 0.0394(12) 0.0828(18) -0.0055(12) 0.0087(15) 0.0005(12)
    C4 0.0611(16) 0.0536(14) 0.0628(16) -0.0115(11) 0.0033(13) 0.0086(12)
    C5 0.0435(13) 0.0575(14) 0.0506(14) -0.0058(11) 0.0010(11) 0.0001(10)
    C6 0.0485(13) 0.0428(12) 0.0603(15) -0.0028(10) 0.0031(13) 0.0009(10)
    C7 0.0404(13) 0.0513(13) 0.0475(12) -0.0027(10) 0.0015(11) 0.0041(10)
    C8 0.0504(13) 0.0497(12) 0.0559(14) 0.0018(11) 0.0016(12) 0.0019(11)
    C9 0.0437(13) 0.0567(13) 0.0520(14) 0.0040(11) 0.0070(11) 0.0015(11)
    C10 0.0466(14) 0.0596(14) 0.0520(14) -0.0004(11) 0.0068(12) 0.0117(11)
    C11 0.0476(14) 0.0469(12) 0.0528(14) 0.0010(10) -0.0006(12) 0.0078(10)
    C12 0.0408(12) 0.0527(13) 0.0500(13) 0.0034(10) 0.0022(10) 0.0020(11)
    C13 0.0599(16) 0.0712(16) 0.0680(17) 0.0075(13) 0.0119(14) 0.0007(13)
    C14 0.0711(18) 0.0562(14) 0.095(2) 0.0124(12) 0.0176(15) -0.0042(13)
_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
    Cl1 C5 . 1.731(2) yes
    O1 C11 . 1.356(2) yes
    O1 C14 . 1.429(2) yes
    O2 C10 . 1.350(2) yes
    O2 H1 . 0.8200 ?
    O3 C13 . 1.221(2) yes
    N1 N2 . 1.252(2) yes
    N1 C1 . 1.431(2) yes
    N2 C7 . 1.420(2) yes
    C1 C6 . 1.378(3) no
    C1 C2 . 1.381(3) no
    C2 C3 . 1.373(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.375(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.374(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.374(3) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.368(3) no
    C7 C12 . 1.408(3) no
    C8 C9 . 1.386(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.394(3) ?
    C9 C13 . 1.445(3) no
    C10 C11 . 1.402(3) ?
    C11 C12 . 1.373(3) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
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
    C11 O1 C14 . . 117.12(16) ?
    C10 O2 H1 . . 109.5 ?
    N2 N1 C1 . . 112.42(15) ?
    N1 N2 C7 . . 115.53(16) ?
    C6 C1 C2 . . 119.55(19) ?
    C6 C1 N1 . . 116.24(18) ?
    C2 C1 N1 . . 124.19(19) ?
    C3 C2 C1 . . 119.4(2) ?
    C3 C2 H2 . . 120.3 ?
    C1 C2 H2 . . 120.3 ?
    C2 C3 C4 . . 121.7(2) ?
    C2 C3 H3 . . 119.2 ?
    C4 C3 H3 . . 119.2 ?
    C5 C4 C3 . . 118.3(2) ?
    C5 C4 H4 . . 120.9 ?
    C3 C4 H4 . . 120.9 ?
    C4 C5 C6 . . 121.1(2) ?
    C4 C5 Cl1 . . 119.30(17) yes
    C6 C5 Cl1 . . 119.61(16) yes
    C5 C6 C1 . . 120.03(19) ?
    C5 C6 H6 . . 120.0 ?
    C1 C6 H6 . . 120.0 ?
    C8 C7 C12 . . 120.01(19) ?
    C8 C7 N2 . . 115.82(18) ?
    C12 C7 N2 . . 124.15(18) ?
    C7 C8 C9 . . 121.11(18) ?
    C7 C8 H8 . . 119.4 ?
    C9 C8 H8 . . 119.4 ?
    C8 C9 C10 . . 118.78(19) ?
    C8 C9 C13 . . 120.63(19) ?
    C10 C9 C13 . . 120.6(2) ?
    O2 C10 C9 . . 122.14(19) yes
    O2 C10 C11 . . 117.12(18) yes
    C9 C10 C11 . . 120.74(19) ?
    O1 C11 C12 . . 125.87(19) yes
    O1 C11 C10 . . 114.77(18) ?
    C12 C11 C10 . . 119.35(18) ?
    C11 C12 C7 . . 120.00(19) ?
    C11 C12 H12 . . 120.0 ?
    C7 C12 H12 . . 120.0 ?
    O3 C13 C9 . . 124.5(2) yes
    O3 C13 H13 . . 117.7 ?
    C9 C13 H13 . . 117.7 ?
    O1 C14 H14A . . 109.5 ?
    O1 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    O1 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 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
    C1 N1 N2 C7 . . . . -178.02(16) no
    N2 N1 C1 C6 . . . . -170.77(18) ?
    N2 N1 C1 C2 . . . . 11.0(3) yes
    C6 C1 C2 C3 . . . . 0.9(3) ?
    N1 C1 C2 C3 . . . . 179.1(2) ?
    C1 C2 C3 C4 . . . . 0.3(4) ?
    C2 C3 C4 C5 . . . . -0.9(4) ?
    C3 C4 C5 C6 . . . . 0.5(3) ?
    C3 C4 C5 Cl1 . . . . -178.32(17) ?
    C4 C5 C6 C1 . . . . 0.7(3) ?
    Cl1 C5 C6 C1 . . . . 179.47(15) no
    C2 C1 C6 C5 . . . . -1.4(3) ?
    N1 C1 C6 C5 . . . . -179.70(18) ?
    N1 N2 C7 C8 . . . . 176.46(18) yes
    N1 N2 C7 C12 . . . . -2.3(3) ?
    C12 C7 C8 C9 . . . . 0.4(3) ?
    N2 C7 C8 C9 . . . . -178.47(19) ?
    C7 C8 C9 C10 . . . . -0.6(3) ?
    C7 C8 C9 C13 . . . . 178.6(2) ?
    C8 C9 C10 O2 . . . . 179.9(2) ?
    C13 C9 C10 O2 . . . . 0.7(3) ?
    C8 C9 C10 C11 . . . . 0.3(3) ?
    C13 C9 C10 C11 . . . . -178.9(2) ?
    C14 O1 C11 C12 . . . . -0.9(3) ?
    C14 O1 C11 C10 . . . . -179.73(19) ?
    O2 C10 C11 O1 . . . . -0.4(3) ?
    C9 C10 C11 O1 . . . . 179.22(18) no
    O2 C10 C11 C12 . . . . -179.33(19) ?
    C9 C10 C11 C12 . . . . 0.3(3) ?
    O1 C11 C12 C7 . . . . -179.33(19) ?
    C10 C11 C12 C7 . . . . -0.5(3) ?
    C8 C7 C12 C11 . . . . 0.2(3) ?
    N2 C7 C12 C11 . . . . 178.96(19) ?
    C8 C9 C13 O3 . . . . -177.8(2) ?
    C10 C9 C13 O3 . . . . 1.4(3) ?
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
    O2 H1 O3 . 0.82 1.91 2.629(2) 146 yes
    C13 H13 O1 7_665 0.93 2.83 3.531(3) 133 yes
