#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/40/2204044.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_2204044
loop_
_publ_author_name
'Orhan Büyükgüngör'
'Nezihe Çalışkan'
'Ceyda Davran'
'Hümeyra Batı'
_publ_section_title
;
 2-(Benzothiazol-2-yliminomethyl)-6-methoxyphenol
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1414
_journal_page_last               o1416
_journal_paper_doi               10.1107/S1600536804018008
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C15 H12 N2 O2 S'
_chemical_formula_moiety         'C15 H12 N2 O2 S'
_chemical_formula_sum            'C15 H12 N2 O2 S'
_chemical_formula_weight         284.33
_chemical_name_systematic
;
2-(Benzothiazol-2-yliminomethyl)-6-methoxyphenol
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.854(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0117(12)
_cell_length_b                   6.3408(4)
_cell_length_c                   17.5237(15)
_cell_measurement_reflns_used    9583
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.27
_cell_measurement_theta_min      2.41
_cell_volume                     1351.1(2)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_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       'rotation method'
_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  0.0885
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9072
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_correction_T_min  0.8808
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.486
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0500
_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)+(0.0793P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1327
_reflns_number_gt                1893
_reflns_number_total             2642
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6071.cif
_cod_data_source_block           I
_cod_original_cell_volume        1351.07(19)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2204044
_cod_database_fobs_code          2204044
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_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
C1 0.76581(19) 0.8859(3) 0.45910(14) 0.0546(5) Uani d . 1 C
C2 0.8509(2) 1.0261(4) 0.46348(17) 0.0721(7) Uani d . 1 C
H2 0.8943 1.0034 0.4320 0.087 Uiso calc R 1 H
C3 0.8695(2) 1.1956(4) 0.51416(18) 0.0761(8) Uani d . 1 C
H3 0.9273 1.2864 0.5181 0.091 Uiso calc R 1 H
C4 0.8039(2) 1.2360(4) 0.56023(17) 0.0696(7) Uani d . 1 C
H4 0.8177 1.3541 0.5938 0.083 Uiso calc R 1 H
C5 0.7189(2) 1.1023(4) 0.55644(15) 0.0615(6) Uani d . 1 C
H5 0.6742 1.1296 0.5865 0.074 Uiso calc R 1 H
C6 0.70159(18) 0.9264(3) 0.50670(13) 0.0519(5) Uani d . 1 C
C7 0.65502(18) 0.6153(3) 0.42069(14) 0.0505(5) Uani d . 1 C
C8 0.62755(19) 0.3555(3) 0.32307(15) 0.0565(5) Uani d . 1 C
H8 0.6791 0.4242 0.3064 0.068 Uiso calc R 1 H
C9 0.57743(19) 0.1659(3) 0.28201(14) 0.0546(5) Uani d . 1 C
C10 0.49954(18) 0.0557(3) 0.30458(13) 0.0501(5) Uani d . 1 C
C11 0.4532(2) -0.1304(3) 0.26519(14) 0.0568(5) Uani d . 1 C
C12 0.4808(3) -0.2026(4) 0.20097(17) 0.0734(7) Uani d . 1 C
H12 0.4487 -0.3250 0.1735 0.088 Uiso calc R 1 H
C13 0.5569(3) -0.0918(4) 0.17720(17) 0.0820(9) Uani d . 1 C
H13 0.5752 -0.1409 0.1336 0.098 Uiso calc R 1 H
C14 0.6048(2) 0.0866(4) 0.21674(16) 0.0731(7) Uani d . 1 C
H14 0.6563 0.1571 0.2005 0.088 Uiso calc R 1 H
C15 0.3229(3) -0.4055(4) 0.2546(2) 0.0887(9) Uani d . 1 C
H15A 0.2769 -0.4557 0.2831 0.133 Uiso calc R 1 H
H15B 0.3735 -0.5144 0.2533 0.133 Uiso calc R 1 H
H15C 0.2781 -0.3676 0.1998 0.133 Uiso calc R 1 H
N1 0.73823(16) 0.7096(3) 0.41057(13) 0.0579(5) Uani d . 1 N
N2 0.60332(15) 0.4331(3) 0.38217(11) 0.0517(4) Uani d . 1 N
O1 0.46650(13) 0.1239(2) 0.36516(9) 0.0583(4) Uani d . 1 O
H1 0.4985 0.2339 0.3841 0.087 Uiso calc R 1 H
O2 0.38241(15) -0.2265(2) 0.29546(11) 0.0685(5) Uani d . 1 O
S1 0.60437(5) 0.72910(9) 0.49008(4) 0.0581(2) Uani d . 1 S
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
N1 C1 C6 116.04(19) ?
N1 C1 C2 125.3(2) ?
C6 C1 C2 118.7(2) ?
C3 C2 C1 119.4(2) ?
C3 C2 H2 120.3 ?
C1 C2 H2 120.3 ?
C2 C3 C4 121.4(2) ?
C2 C3 H3 119.3 ?
C4 C3 H3 119.3 ?
C5 C4 C3 120.5(2) ?
C5 C4 H4 119.8 ?
C3 C4 H4 119.8 ?
C4 C5 C6 118.3(2) ?
C4 C5 H5 120.8 ?
C6 C5 H5 120.8 ?
C5 C6 C1 121.7(2) ?
C5 C6 S1 129.39(17) ?
C1 C6 S1 108.87(16) ?
N1 C7 N2 126.81(19) yes
N1 C7 S1 116.51(17) ?
N2 C7 S1 116.67(14) yes
N2 C8 C9 121.90(19) ?
N2 C8 H8 119.0 ?
C9 C8 H8 119.0 ?
C10 C9 C14 118.0(2) ?
C10 C9 C8 121.54(18) ?
C14 C9 C8 120.4(2) ?
O1 C10 C11 117.30(19) yes
O1 C10 C9 121.84(19) yes
C11 C10 C9 120.86(19) ?
O2 C11 C12 125.5(2) yes
O2 C11 C10 114.85(19) yes
C12 C11 C10 119.7(2) ?
C11 C12 C13 119.8(2) ?
C11 C12 H12 120.1 ?
C13 C12 H12 120.1 ?
C14 C13 C12 120.9(2) ?
C14 C13 H13 119.5 ?
C12 C13 H13 119.5 ?
C13 C14 C9 120.7(2) ?
C13 C14 H14 119.7 ?
C9 C14 H14 119.7 ?
O2 C15 H15A 109.5 ?
O2 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O2 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C7 N1 C1 109.63(18) ?
C8 N2 C7 119.80(18) yes
C10 O1 H1 109.5 ?
C11 O2 C15 119.1(2) ?
C6 S1 C7 88.92(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.373(3) yes
C1 C6 1.399(3) ?
C1 C2 1.401(3) ?
C2 C3 1.360(4) ?
C2 H2 0.9300 ?
C3 C4 1.392(4) ?
C3 H3 0.9300 ?
C4 C5 1.376(3) ?
C4 H4 0.9300 ?
C5 C6 1.384(3) ?
C5 H5 0.9300 ?
C6 S1 1.729(2) yes
C7 N1 1.303(3) yes
C7 N2 1.385(3) yes
C7 S1 1.733(2) yes
C8 N2 1.283(3) yes
C8 C9 1.433(3) ?
C8 H8 0.9300 ?
C9 C10 1.399(3) ?
C9 C14 1.407(3) ?
C10 O1 1.350(2) yes
C10 C11 1.391(3) ?
C11 O2 1.360(3) yes
C11 C12 1.376(3) ?
C12 C13 1.394(4) ?
C12 H12 0.9300 ?
C13 C14 1.357(4) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 O2 1.416(3) yes
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
O1 H1 0.8200 ?
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 N2 . 0.82 1.87 2.593(2) 147
C5 H5 O2 3_666 0.93 2.51 3.395(3) 160
O1 H1 S1 3_666 0.82 2.97 3.1336(14) 94
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
N1 C1 C2 C3 179.9(2) ?
C6 C1 C2 C3 0.7(4) ?
C1 C2 C3 C4 -1.7(5) ?
C2 C3 C4 C5 1.0(5) ?
C3 C4 C5 C6 0.9(4) ?
C4 C5 C6 C1 -1.9(4) ?
C4 C5 C6 S1 178.95(19) ?
N1 C1 C6 C5 -178.1(2) ?
C2 C1 C6 C5 1.2(4) ?
N1 C1 C6 S1 1.2(3) ?
C2 C1 C6 S1 -179.53(19) ?
N2 C8 C9 C10 -0.1(4) yes
N2 C8 C9 C14 179.2(2) ?
C14 C9 C10 O1 -178.3(2) yes
C8 C9 C10 O1 1.0(4) ?
C14 C9 C10 C11 2.0(3) ?
C8 C9 C10 C11 -178.7(2) ?
O1 C10 C11 O2 -2.5(3) ?
C9 C10 C11 O2 177.2(2) ?
O1 C10 C11 C12 177.5(2) ?
C9 C10 C11 C12 -2.7(4) ?
O2 C11 C12 C13 -178.3(3) ?
C10 C11 C12 C13 1.6(4) ?
C11 C12 C13 C14 0.2(4) ?
C12 C13 C14 C9 -1.0(4) ?
C10 C9 C14 C13 -0.1(4) ?
C8 C9 C14 C13 -179.4(3) ?
N2 C7 N1 C1 179.7(2) ?
S1 C7 N1 C1 -0.7(3) yes
C6 C1 N1 C7 -0.3(3) ?
C2 C1 N1 C7 -179.6(2) ?
C9 C8 N2 C7 179.2(2) ?
N1 C7 N2 C8 -9.0(4) ?
S1 C7 N2 C8 171.46(17) yes
C12 C11 O2 C15 -6.1(4) ?
C10 C11 O2 C15 173.9(2) ?
C5 C6 S1 C7 178.0(2) yes
C1 C6 S1 C7 -1.23(18) yes
N1 C7 S1 C6 1.19(19) yes
N2 C7 S1 C6 -179.19(18) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654757
