#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/51/2225171.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_2225171
loop_
_publ_author_name
'Yazıcı, Serap'
'Albayrak, Çiğdem'
'Gümrükçüoğlu, İsmail'
'Şenel, İsmet'
'Büyükgüngör, Orhan'
_publ_section_title
;
 (E)-2-Acetyl-4-[(3-methylphenyl)diazenyl]phenol: an X-ray and
 DFT study
;
_journal_coeditor_code           BT5181
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o559
_journal_page_last               o560
_journal_paper_doi               10.1107/S1600536810003491
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H14 N2 O2'
_chemical_formula_moiety         'C15 H14 N2 O2'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_chemical_name_systematic
;
(E)-2-Acetyl-4-[(3-methylphenyl)diazenyl]phenol
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.881(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6917(3)
_cell_length_b                   10.9728(3)
_cell_length_c                   14.6150(5)
_cell_measurement_reflns_used    20945
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      1.86
_cell_volume                     1284.19(8)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_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) and GAUSSIAN (Frisch et al., 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16525
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.39
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_correction_T_min  0.9565
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.373
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0600
_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)+(0.0859P)²+0.7485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.1749
_reflns_number_gt                2034
_reflns_number_total             2519
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bt5181.cif
_cod_data_source_block           I
_cod_original_cell_volume        1284.19(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225171
_cod_database_fobs_code          2225171
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_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 0.7697(3) 0.49666(19) 0.56898(15) 0.0354(5) Uani d U 1 . .
C C2 0.7798(2) 0.48461(19) 0.66522(14) 0.0337(5) Uani d . 1 . .
H H2 0.7188 0.5371 0.6882 0.040 Uiso calc R 1 . .
C C3 0.8796(3) 0.39527(19) 0.72861(15) 0.0340(5) Uani d . 1 . .
C C4 0.9690(3) 0.3160(2) 0.69197(16) 0.0385(5) Uani d . 1 . .
C C5 0.9567(3) 0.3271(2) 0.59383(17) 0.0433(5) Uani d . 1 . .
H H5 1.0150 0.2737 0.5695 0.052 Uiso calc R 1 . .
C C6 0.8588(3) 0.4165(2) 0.53369(15) 0.0410(5) Uani d . 1 . .
H H6 0.8517 0.4240 0.4688 0.049 Uiso calc R 1 . .
C C7 0.8963(3) 0.3858(2) 0.83278(16) 0.0396(5) Uani d . 1 . .
C C8 0.8087(3) 0.4746(3) 0.87272(17) 0.0506(6) Uani d . 1 . .
H H8A 0.8323 0.4560 0.9410 0.076 Uiso calc R 1 . .
H H8B 0.6905 0.4695 0.8350 0.076 Uiso calc R 1 . .
H H8C 0.8467 0.5556 0.8679 0.076 Uiso calc R 1 . .
C C9 0.5627(3) 0.7083(2) 0.37340(17) 0.0392(5) Uani d U 1 . .
C C10 0.5540(3) 0.7208(2) 0.27821(17) 0.0460(6) Uani d . 1 . .
H H10 0.6146 0.6692 0.2543 0.055 Uiso calc R 1 . .
C C11 0.4544(3) 0.8107(2) 0.21837(18) 0.0482(6) Uani d . 1 . .
H H11 0.4465 0.8197 0.1534 0.058 Uiso calc R 1 . .
C C12 0.3654(3) 0.8882(2) 0.25587(17) 0.0447(6) Uani d . 1 . .
H H12 0.2970 0.9479 0.2148 0.054 Uiso calc R 1 . .
C C13 0.3764(3) 0.8785(2) 0.35255(17) 0.0426(5) Uani d . 1 . .
C C14 0.4774(3) 0.7866(2) 0.41242(16) 0.0426(5) Uani d U 1 . .
H H14 0.4875 0.7778 0.4778 0.051 Uiso calc R 1 . .
C C15 0.2821(3) 0.9642(3) 0.39089(19) 0.0546(7) Uani d . 1 . .
H H15A 0.3037 0.9448 0.4588 0.082 Uiso calc R 1 . .
H H15B 0.1647 0.9566 0.3517 0.082 Uiso calc R 1 . .
H H15C 0.3171 1.0463 0.3868 0.082 Uiso calc R 1 . .
N N1 0.6655(2) 0.60844(18) 0.42943(14) 0.0435(5) Uani d . 1 . .
N N2 0.6666(2) 0.59649(18) 0.51418(13) 0.0431(5) Uani d U 1 . .
O O1 1.0685(2) 0.22765(17) 0.74768(14) 0.0523(5) Uani d . 1 . .
O O2 0.9858(2) 0.30620(17) 0.88764(12) 0.0522(5) Uani d . 1 . .
H H1 1.055(4) 0.235(3) 0.801(3) 0.076(11) Uiso d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 119.43(19) ?
C2 C1 N2 . . 114.66(19) ?
C6 C1 N2 . . 125.89(19) ?
C1 C2 C3 . . 121.3(2) ?
C1 C2 H2 . . 119.3 ?
C3 C2 H2 . . 119.3 ?
C2 C3 C4 . . 118.39(19) ?
C2 C3 C7 . . 121.4(2) ?
C4 C3 C7 . . 120.20(19) ?
O1 C4 C5 . . 117.2(2) ?
O1 C4 C3 . . 122.5(2) ?
C5 C4 C3 . . 120.23(19) ?
C6 C5 C4 . . 120.0(2) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C5 C6 C1 . . 120.6(2) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
O2 C7 C3 . . 120.3(2) ?
O2 C7 C8 . . 119.8(2) ?
C3 C7 C8 . . 119.90(19) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C9 C14 . . 121.7(2) ?
C10 C9 N1 . . 115.3(2) ?
C14 C9 N1 . . 123.0(2) ?
C9 C10 C11 . . 119.3(2) ?
C9 C10 H10 . . 120.4 ?
C11 C10 H10 . . 120.4 ?
C10 C11 C12 . . 119.6(2) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
C13 C12 C11 . . 121.7(2) ?
C13 C12 H12 . . 119.2 ?
C11 C12 H12 . . 119.2 ?
C12 C13 C14 . . 118.2(2) ?
C12 C13 C15 . . 120.3(2) ?
C14 C13 C15 . . 121.5(2) ?
C9 C14 C13 . . 119.5(2) ?
C9 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N2 N1 C9 . . 114.0(2) ?
N1 N2 C1 . . 113.3(2) ?
C4 O1 H1 . . 102(2) ?
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 . 1.381(3) ?
C1 C6 . 1.396(3) ?
C1 N2 . 1.444(3) ?
C2 C3 . 1.395(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.404(3) ?
C3 C7 . 1.476(3) ?
C4 O1 . 1.343(3) ?
C4 C5 . 1.402(3) ?
C5 C6 . 1.371(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O2 . 1.235(3) ?
C7 C8 . 1.488(3) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.371(3) ?
C9 C14 . 1.393(3) ?
C9 N1 . 1.450(3) ?
C10 C11 . 1.378(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.397(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.383(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.398(3) ?
C13 C15 . 1.493(4) ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
N1 N2 . 1.242(3) ?
O1 H1 . 0.83(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 H1 O2 . 0.84(4) 1.78(4) 2.567(3) 156(4)
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 . . . . 1.1(3) ?
N2 C1 C2 C3 . . . . -177.57(18) ?
C1 C2 C3 C4 . . . . -0.8(3) ?
C1 C2 C3 C7 . . . . 177.24(19) ?
C2 C3 C4 O1 . . . . 179.8(2) ?
C7 C3 C4 O1 . . . . 1.7(3) ?
C2 C3 C4 C5 . . . . -0.2(3) ?
C7 C3 C4 C5 . . . . -178.3(2) ?
O1 C4 C5 C6 . . . . -179.1(2) ?
C3 C4 C5 C6 . . . . 0.9(3) ?
C4 C5 C6 C1 . . . . -0.5(3) ?
C2 C1 C6 C5 . . . . -0.5(3) ?
N2 C1 C6 C5 . . . . 178.1(2) ?
C2 C3 C7 O2 . . . . -179.8(2) ?
C4 C3 C7 O2 . . . . -1.8(3) ?
C2 C3 C7 C8 . . . . -1.4(3) ?
C4 C3 C7 C8 . . . . 176.5(2) ?
C14 C9 C10 C11 . . . . -2.0(3) ?
N1 C9 C10 C11 . . . . 177.8(2) ?
C9 C10 C11 C12 . . . . 0.6(3) ?
C10 C11 C12 C13 . . . . 1.0(4) ?
C11 C12 C13 C14 . . . . -1.3(3) ?
C11 C12 C13 C15 . . . . 178.9(2) ?
C10 C9 C14 C13 . . . . 1.8(3) ?
N1 C9 C14 C13 . . . . -178.01(19) ?
C12 C13 C14 C9 . . . . -0.1(3) ?
C15 C13 C14 C9 . . . . 179.7(2) ?
C10 C9 N1 N2 . . . . -177.6(2) ?
C14 C9 N1 N2 . . . . 2.2(3) ?
C9 N1 N2 C1 . . . . -179.99(17) ?
C2 C1 N2 N1 . . . . 177.09(19) ?
C6 C1 N2 N1 . . . . -1.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656009
