#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/74/2207439.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_2207439
loop_
_publ_author_name
'Şahin, Onur'
'Albayrak, Çiğdem'
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 (E)-5-(4-Ethylphenyldiazenyl)salicylaldehyde
;
_journal_coeditor_code           BH6040
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4154
_journal_page_last               o4155
_journal_paper_doi               10.1107/S1600536805036834
_journal_volume                  61
_journal_year                    2005
_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_melting_point          397.5(15)
_chemical_name_systematic
;
(E)-5-(4-Ethylphenyldiazenyl)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                 96.958(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.2617(12)
_cell_length_b                   13.731(2)
_cell_length_c                   6.776(3)
_cell_measurement_reflns_used    2588
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.21
_cell_measurement_theta_min      2.07
_cell_volume                     1317.2(6)
_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, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       ω
_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  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9050
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9465
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.836
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2588
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.835
_refine_ls_R_factor_all          0.1702
_refine_ls_R_factor_gt           0.0490
_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)+(0.0616P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1442
_reflns_number_gt                852
_reflns_number_total             2588
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh6040.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '396-399' was changed to '397.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '396-399' was changed to '397.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1317.2(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207439
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 0.2830(2) 0.63574(19) 0.7142(5) 0.0875(9) Uani d . 1 . . C
C2 0.3042(2) 0.6199(2) 0.9175(5) 0.0968(9) Uani d . 1 . . C
C3 0.3942(2) 0.6062(2) 1.0001(5) 0.1113(11) Uani d . 1 . . C
H3 0.4076 0.5949 1.1359 0.134 Uiso calc R 1 . . H
C4 0.4655(2) 0.6092(2) 0.8821(5) 0.0961(9) Uani d . 1 . . C
H4 0.5275 0.6005 0.9402 0.115 Uiso calc R 1 . . H
C5 0.4487(2) 0.62479(18) 0.6805(4) 0.0779(8) Uani d . 1 . . C
C6 0.3577(2) 0.63832(19) 0.5970(4) 0.0891(9) Uani d . 1 . . C
H6 0.3450 0.6494 0.4610 0.107 Uiso calc R 1 . . H
C7 0.1882(2) 0.6494(2) 0.6250(6) 0.1181(12) Uani d . 1 . . C
H7 0.1787 0.6590 0.4881 0.142 Uiso calc R 1 . . H
C8 0.6722(2) 0.61283(19) 0.5065(4) 0.0785(8) Uani d . 1 A . C
C9 0.7602(2) 0.5852(2) 0.5936(4) 0.0986(9) Uani d . 1 . . C
H9 0.7679 0.5626 0.7239 0.118 Uiso calc R 1 . . H
C10 0.8374(2) 0.5907(3) 0.4894(6) 0.1202(12) Uani d . 1 A . C
H10 0.8966 0.5723 0.5507 0.144 Uiso calc R 1 . . H
C11 0.8278(3) 0.6231(3) 0.2961(7) 0.1274(13) Uani d . 1 . . C
C12 0.7392(3) 0.6505(2) 0.2107(5) 0.1147(11) Uani d . 1 A . C
H12 0.7313 0.6727 0.0800 0.138 Uiso calc R 1 . . H
C13 0.6623(2) 0.6459(2) 0.3139(5) 0.0908(9) Uani d . 1 . . C
H13 0.6033 0.6652 0.2532 0.109 Uiso calc R 1 A . H
C14A 0.9154(13) 0.6618(12) 0.197(3) 0.163(4) Uani d P 0.478(9) A 1 C
H14A 0.8932 0.6994 0.0787 0.195 Uiso calc PR 0.478(9) A 1 H
H14B 0.9533 0.7043 0.2887 0.195 Uiso calc PR 0.478(9) A 1 H
C14B 0.9031(12) 0.6027(9) 0.150(3) 0.163(4) Uani d P 0.522(9) A 2 C
H14C 0.9171 0.5336 0.1465 0.195 Uiso calc PR 0.522(9) A 2 H
H14D 0.8799 0.6241 0.0169 0.195 Uiso calc PR 0.522(9) A 2 H
C15A 0.9680(10) 0.5879(11) 0.147(3) 0.201(4) Uani d P 0.478(9) A 1 C
H15A 1.0244 0.6126 0.1009 0.301 Uiso calc PR 0.478(9) A 1 H
H15B 0.9329 0.5506 0.0431 0.301 Uiso calc PR 0.478(9) A 1 H
H15C 0.9845 0.5471 0.2608 0.301 Uiso calc PR 0.478(9) A 1 H
C15B 0.9842(10) 0.6554(10) 0.225(2) 0.201(4) Uani d P 0.522(9) A 2 C
H15D 1.0324 0.6459 0.1392 0.301 Uiso calc PR 0.522(9) A 2 H
H15E 1.0066 0.6328 0.3560 0.301 Uiso calc PR 0.522(9) A 2 H
H15F 0.9689 0.7233 0.2295 0.301 Uiso calc PR 0.522(9) A 2 H
N1 0.52041(18) 0.62813(15) 0.5508(3) 0.0830(7) Uani d . 1 A . N
N2 0.59986(19) 0.60685(16) 0.6323(3) 0.0855(7) Uani d . 1 . . N
O1 0.11825(16) 0.64973(17) 0.7128(4) 0.1391(10) Uani d . 1 . . O
O2 0.2328(2) 0.6169(2) 1.0378(5) 0.1331(9) Uani d D 1 . . O
H2 0.191(3) 0.615(5) 0.942(7) 0.28(4) Uiso d 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 118.4(3) ?
C2 C1 C7 121.5(3) ?
C6 C1 C7 120.2(3) ?
C3 C2 O2 118.9(4) ?
C3 C2 C1 120.9(3) ?
O2 C2 C1 120.1(4) y
C2 C3 C4 119.3(3) ?
C2 C3 H3 120.3 ?
C4 C3 H3 120.3 ?
C3 C4 C5 122.2(3) ?
C3 C4 H4 118.9 ?
C5 C4 H4 118.9 ?
C6 C5 C4 118.5(3) ?
C6 C5 N1 117.2(3) y
C4 C5 N1 124.3(3) y
C5 C6 C1 120.7(3) ?
C5 C6 H6 119.6 ?
C1 C6 H6 119.6 ?
O1 C7 C1 125.6(4) y
O1 C7 H7 117.2 ?
C1 C7 H7 117.2 ?
C13 C8 C9 118.8(2) ?
C13 C8 N2 126.4(3) ?
C9 C8 N2 114.8(3) y
C8 C9 C10 120.6(3) ?
C8 C9 H9 119.7 ?
C10 C9 H9 119.7 ?
C11 C10 C9 120.8(3) ?
C11 C10 H10 119.6 ?
C9 C10 H10 119.6 ?
C10 C11 C12 118.0(3) ?
C10 C11 C14B 123.1(8) ?
C12 C11 C14B 116.6(9) ?
C10 C11 C14A 121.6(9) ?
C12 C11 C14A 117.4(9) ?
C13 C12 C11 121.5(3) ?
C13 C12 H12 119.3 ?
C11 C12 H12 119.3 ?
C12 C13 C8 120.3(3) ?
C12 C13 H13 119.9 ?
C8 C13 H13 119.9 ?
C15A C14A C11 110.5(13) ?
C15A C14A H14A 109.6 ?
C11 C14A H14A 109.6 ?
C15A C14A H14B 109.6 ?
C11 C14A H14B 109.6 ?
H14A C14A H14B 108.1 ?
C15B C14B C11 106.1(13) ?
C15B C14B H14C 110.5 ?
C11 C14B H14C 110.5 ?
C15B C14B H14D 110.5 ?
C11 C14B H14D 110.5 ?
H14C C14B H14D 108.7 ?
C14B C15B H15D 109.5 ?
C14B C15B H15E 109.5 ?
H15D C15B H15E 109.5 ?
C14B C15B H15F 109.5 ?
H15D C15B H15F 109.5 ?
H15E C15B H15F 109.5 ?
N2 N1 C5 113.9(3) ?
N1 N2 C8 114.4(3) ?
C2 O2 H2 93(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.392(4) ?
C1 C6 1.404(3) ?
C1 C7 1.425(4) ?
C2 C3 1.350(4) ?
C2 O2 1.380(3) y
C3 C4 1.369(4) ?
C3 H3 0.9300 ?
C4 C5 1.375(3) ?
C4 H4 0.9300 ?
C5 C6 1.364(4) ?
C5 N1 1.428(3) y
C6 H6 0.9300 ?
C7 O1 1.222(3) y
C7 H7 0.9300 ?
C8 C13 1.373(4) ?
C8 C9 1.375(4) ?
C8 N2 1.418(3) y
C9 C10 1.379(4) ?
C9 H9 0.9300 ?
C10 C11 1.375(5) ?
C10 H10 0.9300 ?
C11 C12 1.378(4) ?
C11 C14B 1.570(15) ?
C11 C14A 1.581(15) ?
C12 C13 1.371(4) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14A C15A 1.33(3) ?
C14A H14A 0.9700 ?
C14A H14B 0.9700 ?
C14B C15B 1.40(3) ?
C14B H14C 0.9700 ?
C14B H14D 0.9700 ?
C15A H15A 0.9600 ?
C15A H15B 0.9600 ?
C15A H15C 0.9600 ?
C15B H15D 0.9600 ?
C15B H15E 0.9600 ?
C15B H15F 0.9600 ?
N1 N2 1.234(3) y
O2 H2 0.82(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
_geom_hbond_publ_flag
O2 H2 O1 . 0.82(2) 1.83(3) 2.618(5) 161(7) yes
C12 H12 Cg(14) 4_555 0.93 3.1405 3.819(3) 131.30 yes
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
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.7(4) ?
C7 C1 C2 C3 179.5(3) ?
C6 C1 C2 O2 179.9(3) ?
C7 C1 C2 O2 0.1(4) ?
O2 C2 C3 C4 -179.9(3) ?
C1 C2 C3 C4 0.8(5) ?
C2 C3 C4 C5 -0.7(5) ?
C3 C4 C5 C6 0.5(5) ?
C3 C4 C5 N1 -179.7(3) ?
C4 C5 C6 C1 -0.4(4) ?
N1 C5 C6 C1 179.8(2) ?
C2 C1 C6 C5 0.5(4) ?
C7 C1 C6 C5 -179.6(3) ?
C2 C1 C7 O1 0.7(5) ?
C6 C1 C7 O1 -179.1(3) ?
C13 C8 C9 C10 0.1(4) ?
N2 C8 C9 C10 -177.8(3) ?
C8 C9 C10 C11 -0.5(5) ?
C9 C10 C11 C12 0.5(6) ?
C9 C10 C11 C14B -161.2(7) ?
C9 C10 C11 C14A 160.2(7) ?
C10 C11 C12 C13 -0.1(6) ?
C14B C11 C12 C13 162.9(6) ?
C14A C11 C12 C13 -160.6(7) ?
C11 C12 C13 C8 -0.4(5) ?
C9 C8 C13 C12 0.4(4) ?
N2 C8 C13 C12 178.0(3) ?
C10 C11 C14A C15A 76.8(17) ?
C12 C11 C14A C15A -123.5(15) ?
C14B C11 C14A C15A -26.4(19) ?
C10 C11 C14B C15B -67.4(13) ?
C12 C11 C14B C15B 130.6(12) ?
C14A C11 C14B C15B 31(2) ?
C6 C5 N1 N2 -173.9(3) ?
C4 C5 N1 N2 6.3(4) ?
C5 N1 N2 C8 -178.2(2) y
C13 C8 N2 N1 4.9(4) ?
C9 C8 N2 N1 -177.3(3) ?
