#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/04/2210456.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_2210456
loop_
_publ_author_name
'Seferoğlu, Zeynel'
'Hökelek, Tuncer'
'Şahin, Ertan'
'Ertan, Nermin'
_publ_section_title
;
 Ethyl
 [2-(2-phenyl-1H-indol-3-yldiazenyl)-1,3-thiazol-4-yl]acetate
;
_journal_coeditor_code           YM2023
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3835
_journal_page_last               o3837
_journal_paper_doi               10.1107/S160053680603128X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C21 H18 N4 O2 S'
_chemical_formula_moiety         'C21 H18 N4 O2 S'
_chemical_formula_sum            'C21 H18 N4 O2 S'
_chemical_formula_weight         390.45
_chemical_name_systematic
;
Ethyl [2-(2-phenyl-1H-indol-3-yldiazenyl)-1,3-thiazol-4-yl]acetate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.2480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.61110(10)
_cell_length_b                   10.5040(2)
_cell_length_c                   17.3345(2)
_cell_measurement_reflns_used    8200
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30.5069
_cell_measurement_theta_min      2.0977
_cell_volume                     1901.26(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_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      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID-S'
_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  0.0771
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            36040
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.9713
_exptl_absorpt_correction_T_min  0.9348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0782
_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)+(0.0449P)²+0.4823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1616
_reflns_number_gt                3501
_reflns_number_total             5786
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ym2023.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210456
_cod_database_fobs_code          2210456
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_occupancy
S S1 0.43322(6) 0.45119(7) 0.18283(4) 0.0661(2) Uani d 1
O O1 0.73623(19) 0.4843(2) 0.42446(12) 0.0901(7) Uani d 1
O O2 0.88710(15) 0.62048(17) 0.40486(10) 0.0635(5) Uani d 1
N N 0.40102(17) 0.71137(19) 0.18711(11) 0.0540(5) Uani d 1
N N' 0.28557(17) 0.67645(19) 0.15895(10) 0.0506(5) Uani d 1
N N1 0.01480(19) 0.8701(2) 0.09666(12) 0.0570(5) Uani d 1
N N3 0.59946(16) 0.61959(19) 0.24134(11) 0.0542(5) Uani d 1
C C2 0.4812(2) 0.6065(2) 0.20544(13) 0.0485(5) Uani d 1
C C4 0.6573(2) 0.5024(2) 0.25295(14) 0.0537(6) Uani d 1
C C5 0.5838(2) 0.4026(3) 0.22541(17) 0.0649(7) Uani d 1
C C6 0.7930(2) 0.4974(3) 0.29648(17) 0.0630(7) Uani d 1
C C7 0.8008(2) 0.5315(3) 0.38129(16) 0.0621(7) Uani d 1
C C8 0.9049(3) 0.6572(3) 0.48832(17) 0.0729(8) Uani d 1
C C9 1.0081(4) 0.7528(5) 0.5024(2) 0.0982(12) Uani d 1
C C10 0.2016(2) 0.7747(2) 0.13902(13) 0.0496(5) Uani d 1
C C11 0.2242(2) 0.9103(2) 0.13926(13) 0.0503(5) Uani d 1
C C12 0.3313(2) 0.9894(3) 0.15871(15) 0.0569(6) Uani d 1
C C13 0.3143(3) 1.1185(3) 0.15185(17) 0.0668(7) Uani d 1
C C14 0.1949(3) 1.1728(3) 0.12612(17) 0.0687(7) Uani d 1
C C15 0.0875(3) 1.0974(3) 0.10529(16) 0.0643(7) Uani d 1
C C16 0.1048(2) 0.9668(2) 0.11197(14) 0.0528(6) Uani d 1
C C17 0.0703(2) 0.7543(2) 0.11305(13) 0.0513(5) Uani d 1
C C18 -0.0072(2) 0.6374(2) 0.10495(14) 0.0547(6) Uani d 1
C C19 -0.1262(3) 0.6345(4) 0.0580(2) 0.0941(11) Uani d 1
C C20 -0.2000(4) 0.5259(4) 0.0525(3) 0.1160(15) Uani d 1
C C21 -0.1578(3) 0.4194(4) 0.0938(2) 0.0887(10) Uani d 1
C C22 -0.0405(3) 0.4194(3) 0.14095(19) 0.0699(7) Uani d 1
C C23 0.0355(2) 0.5275(3) 0.14619(16) 0.0608(6) Uani d 1
H H1 -0.072(2) 0.882(2) 0.0820(14) 0.067(8) Uiso d 1
H H5 0.607(3) 0.320(3) 0.2296(16) 0.086(9) Uiso d 1
H H12 0.414(2) 0.948(2) 0.1802(14) 0.071(8) Uiso d 1
H H13 0.389(3) 1.169(3) 0.1670(16) 0.087(9) Uiso d 1
H H14 0.186(3) 1.264(3) 0.1218(17) 0.096(10) Uiso d 1
H H15 0.001(2) 1.133(2) 0.0839(14) 0.068(7) Uiso d 1
H H19 -0.154(3) 0.709(3) 0.0262(19) 0.108(11) Uiso d 1
H H20 -0.280(4) 0.530(4) 0.016(2) 0.140(14) Uiso d 1
H H21 -0.212(3) 0.353(3) 0.0916(16) 0.084(9) Uiso d 1
H H22 -0.012(3) 0.343(3) 0.1724(18) 0.108(11) Uiso d 1
H H23 0.122(3) 0.527(3) 0.1844(15) 0.076(8) Uiso d 1
H H61 0.822(3) 0.410(3) 0.2936(16) 0.087(9) Uiso d 1
H H62 0.853(3) 0.551(3) 0.2724(16) 0.078(9) Uiso d 1
H H81 0.818(3) 0.691(3) 0.4973(15) 0.082(9) Uiso d 1
H H82 0.919(3) 0.574(3) 0.5208(18) 0.094(10) Uiso d 1
H H91 1.093(4) 0.723(4) 0.486(2) 0.132(14) Uiso d 1
H H92 1.025(3) 0.775(3) 0.556(2) 0.109(12) Uiso d 1
H H93 0.976(4) 0.836(5) 0.469(2) 0.151(18) 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'
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
C5 S1 C2 88.19(13) yes
C7 O2 C8 116.7(2) ?
N' N C2 111.23(19) yes
N N' C10 114.4(2) yes
C17 N1 C16 110.93(19) yes
C17 N1 H1 123.7(16) ?
C16 N1 H1 125.1(16) ?
C2 N3 C4 109.96(19) yes
N3 C2 N 121.4(2) yes
N3 C2 S1 115.24(17) yes
N C2 S1 123.32(16) yes
C5 C4 N3 115.6(2) yes
C5 C4 C6 126.6(2) ?
N3 C4 C6 117.8(2) ?
C4 C5 S1 111.0(2) yes
C4 C5 H5 126.3(18) ?
S1 C5 H5 122.6(18) ?
C7 C6 C4 111.3(2) ?
C7 C6 H62 110.3(16) ?
C4 C6 H62 113.1(16) ?
C7 C6 H61 108.2(17) ?
C4 C6 H61 106.8(17) ?
H62 C6 H61 107(2) ?
O1 C7 O2 122.5(3) ?
O1 C7 C6 124.8(3) ?
O2 C7 C6 112.7(2) ?
C9 C8 O2 107.6(3) ?
C9 C8 H81 113.9(16) ?
O2 C8 H81 106.0(15) ?
C9 C8 H82 117.0(17) ?
O2 C8 H82 107.0(17) ?
H81 C8 H82 105(2) ?
C8 C9 H91 114(2) ?
C8 C9 H92 110(2) ?
H91 C9 H92 109(3) ?
C8 C9 H93 108(2) ?
H91 C9 H93 108(3) ?
H92 C9 H93 109(3) ?
N' C10 C17 122.1(2) yes
N' C10 C11 130.0(2) yes
C17 C10 C11 107.9(2) yes
C12 C11 C16 118.4(2) ?
C12 C11 C10 135.5(2) ?
C16 C11 C10 106.1(2) ?
C13 C12 C11 118.5(2) ?
C13 C12 H12 124.2(15) ?
C11 C12 H12 117.1(15) ?
C12 C13 C14 122.2(3) ?
C12 C13 H13 116.1(19) ?
C14 C13 H13 121.7(19) ?
C15 C14 C13 120.8(3) ?
C15 C14 H14 119.0(18) ?
C13 C14 H14 120.2(18) ?
C14 C15 C16 117.0(3) ?
C14 C15 H15 123.1(15) ?
C16 C15 H15 119.8(15) ?
C15 C16 N1 129.2(2) ?
C15 C16 C11 123.1(2) ?
N1 C16 C11 107.7(2) yes
N1 C17 C10 107.4(2) yes
N1 C17 C18 120.8(2) ?
C10 C17 C18 131.7(2) ?
C19 C18 C23 117.8(3) ?
C19 C18 C17 121.0(2) ?
C23 C18 C17 121.2(2) ?
C18 C19 C20 120.7(3) ?
C18 C19 H19 118.2(19) ?
C20 C19 H19 120.9(19) ?
C21 C20 C19 121.0(3) ?
C21 C20 H20 123(2) ?
C19 C20 H20 116(2) ?
C20 C21 C22 119.7(3) ?
C20 C21 H21 118.0(19) ?
C22 C21 H21 122.2(19) ?
C21 C22 C23 119.9(3) ?
C21 C22 H22 119.4(19) ?
C23 C22 H22 120.6(19) ?
C22 C23 C18 120.9(2) ?
C22 C23 H23 118.4(15) ?
C18 C23 H23 120.5(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C5 1.714(3) yes
S1 C2 1.733(2) yes
N C2 1.394(3) yes
N' N 1.289(2) yes
N' C10 1.367(3) yes
N1 C17 1.360(3) yes
N1 H1 0.92(2) ?
N3 C2 1.305(3) yes
N3 C4 1.374(3) yes
O2 C7 1.322(3) ?
O2 C8 1.477(3) ?
C4 C5 1.341(4) yes
C4 C6 1.504(3) ?
C5 H5 0.91(3) ?
C6 H62 1.00(3) ?
C6 H61 0.97(3) ?
C7 O1 1.207(3) ?
C7 C6 1.501(4) ?
C8 C9 1.474(5) ?
C8 H81 1.03(3) ?
C8 H82 1.04(3) ?
C9 H91 1.04(4) ?
C9 H92 0.95(4) ?
C9 H93 1.07(5) ?
C10 C17 1.402(3) yes
C10 C11 1.444(3) yes
C11 C12 1.400(3) ?
C11 C16 1.403(3) yes
C12 H12 1.00(3) ?
C13 C12 1.371(4) ?
C13 C14 1.388(4) ?
C13 H13 0.95(3) ?
C14 C15 1.382(4) ?
C14 H14 0.96(3) ?
C15 H15 1.00(2) ?
C16 C15 1.386(4) ?
C16 N1 1.387(3) ?
C17 C18 1.470(3) ?
C18 C19 1.375(3) ?
C18 C23 1.391(3) ?
C19 C20 1.377(5) ?
C19 H19 0.97(3) ?
C20 H20 0.96(4) ?
C21 C20 1.361(5) ?
C21 H21 0.90(3) ?
C22 C21 1.363(4) ?
C22 H22 0.99(3) ?
C23 C22 1.386(4) ?
C23 H23 1.03(3) ?
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
C5 S1 C2 N3 0.2(2) yes
C5 S1 C2 N -179.9(2) ?
C2 S1 C5 C4 0.2(2) yes
C7 O2 C8 C9 177.8(3) ?
C8 O2 C7 O1 2.1(4) ?
C8 O2 C7 C6 -177.9(2) ?
N' N C2 N3 -173.6(2) ?
N' N C2 S1 6.4(3) ?
C10 N' N C2 -179.50(18) ?
N N' C10 C17 -175.1(2) ?
N N' C10 C11 5.1(3) ?
C16 N1 C17 C10 -0.8(3) yes
C16 N1 C17 C18 177.1(2) ?
C2 N3 C4 C5 0.7(3) yes
C2 N3 C4 C6 -177.7(2) ?
C4 N3 C2 N 179.5(2) ?
C4 N3 C2 S1 -0.5(3) yes
C5 C4 C6 C7 -109.1(3) ?
N3 C4 C6 C7 69.0(3) ?
N3 C4 C5 S1 -0.5(3) yes
C6 C4 C5 S1 177.7(2) ?
O1 C7 C6 C4 51.0(4) ?
O2 C7 C6 C4 -128.9(2) ?
N' C10 C17 N1 -178.7(2) ?
N' C10 C11 C12 -0.5(5) ?
N' C10 C11 C16 178.9(2) ?
N' C10 C17 C18 3.7(4) ?
C11 C10 C17 C18 -176.5(2) ?
C11 C10 C17 N1 1.1(3) yes
C17 C10 C11 C12 179.7(3) ?
C17 C10 C11 C16 -0.9(3) yes
C12 C11 C16 C15 -1.7(4) ?
C10 C11 C16 C15 178.8(2) ?
C12 C11 C16 N1 179.9(2) ?
C10 C11 C16 N1 0.4(3) yes
C16 C11 C12 C13 1.4(4) ?
C10 C11 C12 C13 -179.3(3) ?
C14 C13 C12 C11 -0.2(4) ?
C12 C13 C14 C15 -0.8(5) ?
C13 C14 C15 C16 0.5(4) ?
N1 C16 C15 C14 178.8(2) ?
C11 C16 C15 C14 0.7(4) ?
C15 C16 N1 C17 -178.0(3) ?
C11 C16 N1 C17 0.2(3) yes
N1 C17 C18 C19 21.4(4) ?
C10 C17 C18 C19 -161.2(3) ?
N1 C17 C18 C23 -156.6(2) ?
C10 C17 C18 C23 20.7(4) ?
C19 C18 C23 C22 -1.0(4) ?
C17 C18 C23 C22 177.1(2) ?
C23 C18 C19 C20 0.1(5) ?
C17 C18 C19 C20 -178.1(4) ?
C18 C19 C20 C21 0.6(7) ?
C22 C21 C20 C19 -0.5(7) ?
C23 C22 C21 C20 -0.5(6) ?
C18 C23 C22 C21 1.2(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21178719
