#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/39/2013943.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_2013943
loop_
_publ_author_name
'Ersanlı, Cem Cüneyt'
'Albayrak, Çiǧdem'
'Odabas̨oǧlu, Mustafa'
'Kazak, Canan'
'Erdönmez, Ahmet'
_publ_section_title
;
3-Methoxy-5-(4-methylphenyldiazenyl)salicylaldehyde and
3-methoxy-5-(2-methylphenyldiazenyl)salicylaldehyde
;
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              o455
_journal_page_last               o457
_journal_paper_doi               10.1107/S0108270104010844
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C15 H14 N2 O3'
_chemical_formula_moiety         'C15 H14 N2 O3'
_chemical_formula_sum            'C15 H14 N2 O3'
_chemical_formula_weight         270.28
_chemical_name_systematic
;
3-Methoxy-5-(4-methylphenyldiazenyl)salicylaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 91.842(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.746(5)
_cell_length_b                   12.529(5)
_cell_length_c                   15.556(5)
_cell_measurement_reflns_used    5746
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7
_cell_measurement_theta_min      1.6
_cell_volume                     1314.1(12)
_computing_cell_refinement       'X-AREA '
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.119
_diffrn_reflns_av_sigmaI/netI    0.131
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10018
_diffrn_reflns_theta_full        28.7
_diffrn_reflns_theta_max         28.7
_diffrn_reflns_theta_min         2.1
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.20
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.84
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.84
_refine_ls_R_factor_all          0.082
_refine_ls_R_factor_gt           0.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0583P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.088
_refine_ls_wR_factor_ref         0.098
_reflns_number_gt                1784
_reflns_number_total             3361
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn1045.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013943
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.33622(19) 0.36193(9) 0.40389(8) 0.0444(3) Uani d . 1 . . C
C2 0.3628(2) 0.25298(10) 0.39561(9) 0.0504(3) Uani d . 1 . . C
C3 0.2200(2) 0.18339(10) 0.42316(9) 0.0510(3) Uani d . 1 . . C
C4 0.04802(19) 0.22003(10) 0.45914(8) 0.0470(3) Uani d . 1 . . C
C5 0.0219(2) 0.32943(11) 0.46570(9) 0.0536(3) Uani d . 1 . . C
C6 0.1636(2) 0.39996(11) 0.43900(9) 0.0524(3) Uani d . 1 . . C
C7 0.62022(19) 0.59095(10) 0.35405(8) 0.0456(3) Uani d . 1 . . C
C8 0.79107(19) 0.55422(10) 0.31816(8) 0.0469(3) Uani d . 1 . . C
C9 0.93263(19) 0.62663(9) 0.29046(8) 0.0444(3) Uani d . 1 . . C
C10 0.90115(19) 0.73650(9) 0.29936(8) 0.0448(3) Uani d . 1 . . C
C11 0.72723(19) 0.77318(9) 0.33588(8) 0.0459(3) Uani d . 1 . . C
C12 0.5900(2) 0.70062(10) 0.36292(8) 0.0475(3) Uani d . 1 . . C
C13 1.1077(2) 0.58737(12) 0.24961(9) 0.0529(3) Uani d . 1 . . C
C14 0.5280(2) 0.92439(11) 0.36598(11) 0.0680(4) Uani d . 1 . . C
H14A 0.5054 0.9061 0.4248 0.102 Uiso calc R 1 . . H
H14B 0.4232 0.8957 0.3297 0.102 Uiso calc R 1 . . H
H14C 0.5310 1.0006 0.3601 0.102 Uiso calc R 1 . . H
C15 -0.1063(2) 0.14499(11) 0.49108(10) 0.0640(4) Uani d . 1 . . C
H15A -0.0742 0.1259 0.5497 0.096 Uiso calc R 1 . . H
H15B -0.1097 0.0818 0.4561 0.096 Uiso calc R 1 . . H
H15C -0.2337 0.1792 0.4879 0.096 Uiso calc R 1 . . H
N1 0.49277(16) 0.42766(8) 0.37451(7) 0.0501(3) Uani d . 1 . . N
N2 0.46433(16) 0.52530(8) 0.38410(7) 0.0502(3) Uani d . 1 . . N
O1 1.23469(15) 0.64489(8) 0.21944(7) 0.0635(3) Uani d . 1 . . O
O2 1.03377(15) 0.80895(7) 0.27247(6) 0.0574(3) Uani d . 1 . . O
O3 0.71129(14) 0.88132(7) 0.34145(7) 0.0599(3) Uani d . 1 . . O
H2 0.480(2) 0.2281(11) 0.3673(9) 0.057(4) Uiso d . 1 . . H
H2O 1.130(3) 0.7604(15) 0.2488(12) 0.092(6) Uiso d . 1 . . H
H3 0.242(2) 0.1069(12) 0.4148(9) 0.064(4) Uiso d . 1 . . H
H5 -0.103(3) 0.3568(11) 0.4890(10) 0.072(5) Uiso d . 1 . . H
H6 0.147(2) 0.4743(13) 0.4463(9) 0.066(4) Uiso d . 1 . . H
H8 0.816(2) 0.4810(11) 0.3113(8) 0.053(4) Uiso d . 1 . . H
H12 0.469(2) 0.7224(11) 0.3879(8) 0.049(4) Uiso d . 1 . . H
H13 1.119(2) 0.5073(12) 0.2452(9) 0.059(4) Uiso d . 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 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'
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
C2 C1 C6 119.27(12) ?
C2 C1 N1 116.10(10) yes
C6 C1 N1 124.60(10) yes
C3 C2 C1 120.09(13) ?
C3 C2 H2 121.8(8) ?
C1 C2 H2 118.0(8) ?
C2 C3 C4 121.34(13) ?
C2 C3 H3 118.0(8) ?
C4 C3 H3 120.7(8) ?
C3 C4 C5 117.91(12) ?
C3 C4 C15 121.77(12) ?
C5 C4 C15 120.31(13) ?
C6 C5 C4 121.48(14) ?
C6 C5 H5 119.7(9) ?
C4 C5 H5 118.8(9) ?
C5 C6 C1 119.90(13) ?
C5 C6 H6 120.8(9) ?
C1 C6 H6 119.3(9) ?
C8 C7 C12 119.73(12) ?
C8 C7 N2 125.20(10) yes
C12 C7 N2 115.10(10) yes
C7 C8 C9 119.89(12) ?
C7 C8 H8 121.9(8) ?
C9 C8 H8 118.2(8) ?
C8 C9 C10 120.07(12) ?
C8 C9 C13 119.44(12) ?
C10 C9 C13 120.44(11) ?
O2 C10 C11 118.6(2) yes
O2 C10 C9 121.7(2) yes
C11 C10 C9 119.70(10) yes
O3 C11 C12 125.7(2) yes
O3 C11 C10 114.9(2) yes
C12 C11 C10 119.33(12) ?
C11 C12 C7 121.28(13) ?
C11 C12 H12 122.0(8) ?
C7 C12 H12 116.7(8) ?
O1 C13 C9 124.10(10) yes
O1 C13 H13 120.2(8) ?
C9 C13 H13 115.7(8) ?
O3 C14 H14A 109.5 ?
O3 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
O3 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C4 C15 H15A 109.5 ?
C4 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C4 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
N2 N1 C1 114.2(2) yes
N1 N2 C7 114.1(2) yes
C10 O2 H2O 98.9(10) ?
C11 O3 C14 117.9(2) yes
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 C2 . 1.3832(18) ?
C1 C6 . 1.387(2) ?
C1 N1 . 1.426(2) yes
C2 C3 . 1.3779(19) ?
C2 H2 . 0.971(15) ?
C3 C4 . 1.383(2) ?
C3 H3 . 0.979(15) ?
C4 C5 . 1.3861(19) ?
C4 C15 . 1.4991(19) ?
C5 C6 . 1.375(2) ?
C5 H5 . 0.989(17) ?
C6 H6 . 0.945(16) ?
C7 C8 . 1.3760(19) ?
C7 C12 . 1.3965(19) ?
C7 N2 . 1.426(2) yes
C8 C9 . 1.3954(18) ?
C8 H8 . 0.940(13) ?
C9 C10 . 1.4004(18) ?
C9 C13 . 1.446(2) ?
C10 O2 . 1.350(2) yes
C10 C11 . 1.3976(19) ?
C11 O3 . 1.362(2) yes
C11 C12 . 1.3731(19) ?
C12 H12 . 0.957(14) ?
C13 O1 . 1.224(2) yes
C13 H13 . 1.009(14) ?
C14 O3 . 1.413(2) yes
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
N1 N2 . 1.248(2) yes
O2 H2O . 0.973(19) ?
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
C13 H13 O3 2_745 1.01(2) 2.390(10) 3.205(2) 137.3(10)
C2 H2 O1 2_745 0.97(2) 2.60(2) 3.567(2) 172.7(11)
O2 H2O O1 . 0.97(2) 1.68(2) 2.611(2) 159.1(16)
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
C6 C1 C2 C3 -0.9(2)
N1 C1 C2 C3 179.32(12)
C1 C2 C3 C4 0.2(2)
C2 C3 C4 C5 0.9(2)
C2 C3 C4 C15 -178.64(14)
C3 C4 C5 C6 -1.3(2)
C15 C4 C5 C6 178.25(14)
C4 C5 C6 C1 0.6(2)
C2 C1 C6 C5 0.5(2)
N1 C1 C6 C5 -179.73(13)
C12 C7 C8 C9 -0.31(19)
N2 C7 C8 C9 179.50(12)
C7 C8 C9 C10 0.16(18)
C7 C8 C9 C13 -177.45(12)
C8 C9 C10 O2 -179.28(12)
C13 C9 C10 O2 -1.69(19)
C8 C9 C10 C11 -0.16(18)
C13 C9 C10 C11 177.43(12)
O2 C10 C11 O3 -0.79(17)
C9 C10 C11 O3 -179.93(11)
O2 C10 C11 C12 179.46(12)
C9 C10 C11 C12 0.32(19)
O3 C11 C12 C7 179.80(12)
C10 C11 C12 C7 -0.48(19)
C8 C7 C12 C11 0.48(19)
N2 C7 C12 C11 -179.34(12)
C8 C9 C13 O1 176.18(13)
C10 C9 C13 O1 -1.4(2)
C2 C1 N1 N2 -179.12(12)
C6 C1 N1 N2 1.09(18)
C1 N1 N2 C7 -179.51(10)
C8 C7 N2 N1 -0.78(18)
C12 C7 N2 N1 179.04(11)
C12 C11 O3 C14 -9.2(2)
C10 C11 O3 C14 171.02(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21181363
