#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/58/2205898.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_2205898
loop_
_publ_author_name
'Dinçer, Muharrem'
'Özdemir, Namık'
'Çukurovalı, Alaaddin'
'Yılmaz, İbrahim'
_publ_section_title
;
 2-[(4-Phenylthiazol-2-yl)hydrazonomethyl]phenol
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1712
_journal_page_last               o1714
_journal_paper_doi               10.1107/S1600536805014418
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H13 N3 O S'
_chemical_formula_moiety         'C16 H13 N3 O S'
_chemical_formula_sum            'C16 H13 N3 O S'
_chemical_formula_weight         295.35
_chemical_name_systematic
;
2-[(4-Phenylthiazol-2-yl)hydrazonomethyl]phenol
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.5129(13)
_cell_length_b                   30.047(4)
_cell_length_c                   11.1308(18)
_cell_measurement_reflns_used    9629
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      1.83
_cell_volume                     2847.1(7)
_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) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1385
_diffrn_reflns_av_sigmaI/netI    0.0933
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16710
_diffrn_reflns_theta_full        26.08
_diffrn_reflns_theta_max         26.08
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9772
_exptl_absorpt_correction_T_min  0.8390
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.158
_refine_ls_extinction_coef       0.0014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.1699
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0255P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                1028
_reflns_number_total             2803
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6579.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2205898
_cod_database_fobs_code          2205898
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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_type_symbol
S1 0.01018(13) 0.44538(3) 0.16860(9) 0.0772(3) Uani d . 1 S
O1 -0.2677(3) 0.54708(8) 0.1326(2) 0.0821(8) Uani d . 1 O
H1 -0.2194 0.5278 0.1695 0.123 Uiso calc R 1 H
N1 0.0264(3) 0.40152(10) 0.3672(2) 0.0642(8) Uani d . 1 N
N2 -0.0861(3) 0.47218(10) 0.3876(3) 0.0712(9) Uani d . 1 N
H2A -0.0876 0.4710 0.4648 0.085 Uiso calc R 1 H
N3 -0.1497(3) 0.50792(9) 0.3258(3) 0.0609(7) Uani d . 1 N
C1 -0.0206(4) 0.43865(12) 0.3202(3) 0.0590(8) Uani d . 1 C
C2 0.0931(4) 0.39294(12) 0.1682(4) 0.0728(11) Uani d . 1 C
H2 0.1332 0.3790 0.1002 0.087 Uiso calc R 1 H
C3 0.0926(4) 0.37480(12) 0.2785(3) 0.0620(10) Uani d . 1 C
C4 0.1479(4) 0.33004(12) 0.3129(3) 0.0608(9) Uani d . 1 C
C5 0.2398(5) 0.30519(14) 0.2364(4) 0.0833(11) Uani d . 1 C
H5 0.2702 0.3171 0.1629 0.100 Uiso calc R 1 H
C6 0.2875(5) 0.26270(14) 0.2678(5) 0.0949(14) Uani d . 1 C
H6 0.3506 0.2464 0.2156 0.114 Uiso calc R 1 H
C7 0.2424(5) 0.24448(14) 0.3752(4) 0.0869(12) Uani d . 1 C
H7 0.2741 0.2159 0.3957 0.104 Uiso calc R 1 H
C8 0.1507(5) 0.26850(14) 0.4519(4) 0.0895(14) Uani d . 1 C
H8 0.1191 0.2562 0.5247 0.107 Uiso calc R 1 H
C9 0.1045(5) 0.31150(14) 0.4208(4) 0.0804(12) Uani d . 1 C
H9 0.0433 0.3279 0.4740 0.097 Uiso calc R 1 H
C10 -0.2122(4) 0.53900(12) 0.3903(3) 0.0636(10) Uani d . 1 C
H10 -0.2065 0.5374 0.4736 0.076 Uiso calc R 1 H
C11 -0.2905(4) 0.57615(11) 0.3344(3) 0.0579(9) Uani d . 1 C
C12 -0.3196(4) 0.57904(12) 0.2115(3) 0.0614(10) Uani d . 1 C
C13 -0.4047(4) 0.61435(12) 0.1646(4) 0.0724(11) Uani d . 1 C
H13 -0.4257 0.6156 0.0827 0.087 Uiso calc R 1 H
C14 -0.4578(4) 0.64743(12) 0.2394(4) 0.0756(12) Uani d . 1 C
H14 -0.5147 0.6711 0.2076 0.091 Uiso calc R 1 H
C15 -0.4280(4) 0.64608(13) 0.3604(3) 0.0724(11) Uani d . 1 C
H15 -0.4637 0.6687 0.4105 0.087 Uiso calc R 1 H
C16 -0.3440(4) 0.61060(12) 0.4069(3) 0.0707(11) Uani d . 1 C
H16 -0.3229 0.6098 0.4889 0.085 Uiso calc R 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'
S S 0.1246 0.1234 '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
C1 S1 C2 87.56(19) yes
C12 O1 H1 109.5 ?
C1 N1 C3 109.6(3) yes
C1 N2 N3 117.1(3) yes
C1 N2 H2A 121.5 ?
N3 N2 H2A 121.5 ?
C10 N3 N2 116.4(3) yes
N1 C1 N2 122.4(3) yes
N1 C1 S1 116.8(3) yes
N2 C1 S1 120.8(3) yes
C3 C2 S1 111.5(3) yes
C3 C2 H2 124.2 ?
S1 C2 H2 124.2 ?
C2 C3 N1 114.5(3) yes
C2 C3 C4 127.3(3) yes
N1 C3 C4 118.1(3) yes
C9 C4 C5 118.2(4) ?
C9 C4 C3 120.7(3) ?
C5 C4 C3 121.0(4) ?
C4 C5 C6 120.7(4) ?
C4 C5 H5 119.6 ?
C6 C5 H5 119.6 ?
C7 C6 C5 120.4(4) ?
C7 C6 H6 119.8 ?
C5 C6 H6 119.8 ?
C8 C7 C6 119.7(4) ?
C8 C7 H7 120.2 ?
C6 C7 H7 120.2 ?
C7 C8 C9 119.8(4) ?
C7 C8 H8 120.1 ?
C9 C8 H8 120.1 ?
C4 C9 C8 121.1(4) ?
C4 C9 H9 119.5 ?
C8 C9 H9 119.5 ?
N3 C10 C11 120.7(4) yes
N3 C10 H10 119.7 ?
C11 C10 H10 119.7 ?
C16 C11 C12 117.8(3) ?
C16 C11 C10 118.5(4) ?
C12 C11 C10 123.7(3) ?
O1 C12 C13 117.5(3) yes
O1 C12 C11 121.8(3) yes
C13 C12 C11 120.7(4) ?
C14 C13 C12 119.8(4) ?
C14 C13 H13 120.1 ?
C12 C13 H13 120.1 ?
C15 C14 C13 120.9(4) ?
C15 C14 H14 119.6 ?
C13 C14 H14 119.6 ?
C14 C15 C16 119.1(4) ?
C14 C15 H15 120.5 ?
C16 C15 H15 120.5 ?
C15 C16 C11 121.7(4) ?
C15 C16 H16 119.2 ?
C11 C16 H16 119.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.720(3) yes
S1 C2 1.727(4) yes
O1 C12 1.375(4) yes
O1 H1 0.82 ?
N1 C1 1.296(4) yes
N1 C3 1.392(4) yes
N2 C1 1.374(4) yes
N2 N3 1.385(3) yes
N2 H2A 0.86 ?
N3 C10 1.292(4) yes
C2 C3 1.343(5) yes
C2 H2 0.93 ?
C3 C4 1.475(4) yes
C4 C9 1.375(5) ?
C4 C5 1.376(5) ?
C5 C6 1.385(5) ?
C5 H5 0.93 ?
C6 C7 1.370(5) ?
C6 H6 0.93 ?
C7 C8 1.363(5) ?
C7 H7 0.93 ?
C8 C9 1.394(5) ?
C8 H8 0.93 ?
C9 H9 0.93 ?
C10 C11 1.442(4) yes
C10 H10 0.93 ?
C11 C16 1.390(5) ?
C11 C12 1.392(5) ?
C12 C13 1.387(4) ?
C13 C14 1.373(5) ?
C13 H13 0.93 ?
C14 C15 1.371(5) ?
C14 H14 0.93 ?
C15 C16 1.384(5) ?
C15 H15 0.93 ?
C16 H16 0.93 ?
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 N3 . 0.82 1.93 2.650(4) 145
C9 H9 N1 . 0.93 2.51 2.848(5) 101
C13 H13 N1 2_464 0.93 2.60 3.501(5) 164
N2 H2A O1 2_465 0.86 2.30 3.052(4) 146
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
C1 N2 N3 C10 179.4(3) yes
C3 N1 C1 N2 -177.7(3) yes
C3 N1 C1 S1 -0.4(4) ?
N3 N2 C1 N1 -172.2(3) yes
N3 N2 C1 S1 10.6(4) yes
C2 S1 C1 N1 0.5(3) ?
C2 S1 C1 N2 177.8(3) ?
C1 S1 C2 C3 -0.3(3) ?
S1 C2 C3 N1 0.2(4) ?
S1 C2 C3 C4 177.7(3) ?
C1 N1 C3 C2 0.2(4) ?
C1 N1 C3 C4 -177.6(3) ?
C2 C3 C4 C9 -163.1(4) ?
N1 C3 C4 C9 14.3(5) yes
C2 C3 C4 C5 14.7(6) ?
N1 C3 C4 C5 -167.9(3) yes
C9 C4 C5 C6 -0.2(6) ?
C3 C4 C5 C6 -178.1(4) ?
C4 C5 C6 C7 0.8(7) ?
C5 C6 C7 C8 -0.4(7) ?
C6 C7 C8 C9 -0.4(7) ?
C5 C4 C9 C8 -0.6(6) ?
C3 C4 C9 C8 177.3(4) ?
C7 C8 C9 C4 1.0(6) ?
N2 N3 C10 C11 -175.9(3) yes
N3 C10 C11 C16 -174.6(3) yes
N3 C10 C11 C12 7.2(5) yes
C16 C11 C12 O1 178.4(3) ?
C10 C11 C12 O1 -3.4(6) yes
C16 C11 C12 C13 -2.5(5) ?
C10 C11 C12 C13 175.7(3) ?
O1 C12 C13 C14 -179.3(3) ?
C11 C12 C13 C14 1.6(5) ?
C12 C13 C14 C15 0.0(5) ?
C13 C14 C15 C16 -0.4(6) ?
C14 C15 C16 C11 -0.6(6) ?
C12 C11 C16 C15 2.1(5) ?
C10 C11 C16 C15 -176.3(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12246340
