##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-06-16
_journal_date_accepted     2010-06-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      7
_journal_page_first     o1826
_journal_page_last     o1826
_journal_paper_category     QO
_journal_coeditor_code     NK2043
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
Monoclinic modification of 2-[(1,3-benzothiazol-2-yl)iminomethyl]phenol
;
loop_
    _publ_author_name
    _publ_author_address
    'Asiri, Abdullah M.'
;
Chemistry Department
Faculty of Science
King Abdul Aziz University
PO Box 80203
Jeddah 21589
Saudi Arabia
;
    'Khan,  Salman A.'
;
Chemistry Department
Faculty of Science
King Abdul Aziz University
PO Box 80203
Jeddah 21589
Saudi Arabia
;
    'Tan, Kong Wai'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-[(1,3-benzothiazol-2-yl)iminomethyl]phenol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H10 N2 O S'
_chemical_formula_sum     'C14 H10 N2 O S'
_chemical_formula_iupac     'C14 H10 N2 O S'
_chemical_formula_weight     254.30
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P n'
_symmetry_space_group_name_Hall     'P -2yac'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x+1/2, -y, z+1/2'
_cell_length_a     8.6391(4)
_cell_length_b     6.2313(4)
_cell_length_c     11.4459(8)
_cell_angle_alpha     90.00
_cell_angle_beta     108.8930(10)
_cell_angle_gamma     90.00
_cell_volume     582.97(6)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3896
_cell_measurement_theta_min     2.6
_cell_measurement_theta_max     28.3
_cell_measurement_temperature     100(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Orange
_exptl_crystal_size_max     0.14
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.449
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     264
_exptl_absorpt_coefficient_mu     0.264
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9639
_exptl_absorpt_correction_T_max     0.9792
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5307
_diffrn_reflns_av_R_equivalents     0.0293
_diffrn_reflns_av_sigmaI/netI     0.0385
_diffrn_reflns_theta_min     2.59
_diffrn_reflns_theta_max     27.49
_diffrn_reflns_theta_full     27.49
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     2599
_reflns_number_gt     2512
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0412
_refine_ls_R_factor_gt     0.0399
_refine_ls_wR_factor_gt     0.1080
_refine_ls_wR_factor_ref     0.1096
_refine_ls_goodness_of_fit_ref     1.053
_refine_ls_restrained_S_all     1.053
_refine_ls_number_reflns     2599
_refine_ls_number_parameters     164
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0831P)²+0.0645P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.396
_refine_diff_density_min     -0.254
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1242 Friedel pairs'
_refine_ls_abs_structure_Flack     0.27(8)
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'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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
    S S1 0.50007(6) 0.06429(7) 0.49993(5) 0.01864(15) Uani d . 1 . .
    O O1 0.7048(2) 0.5684(3) 0.89741(16) 0.0277(4) Uani d . 1 . .
    H H1 0.6924 0.4623 0.8462 0.042 Uiso d R 1 . .
    N N1 0.6095(2) 0.3254(3) 0.70823(16) 0.0186(4) Uani d . 1 . .
    N N2 0.7613(2) 0.0261(3) 0.69409(17) 0.0193(4) Uani d . 1 . .
    C C1 0.5700(3) 0.6867(4) 0.84466(19) 0.0195(4) Uani d . 1 . .
    C C2 0.5445(3) 0.8696(4) 0.9059(2) 0.0222(4) Uani d . 1 . .
    H H2 0.6227 0.9096 0.9825 0.027 Uiso calc R 1 . .
    C C3 0.4058(3) 0.9936(4) 0.8561(2) 0.0226(5) Uani d . 1 . .
    H H3 0.3895 1.1183 0.8985 0.027 Uiso calc R 1 . .
    C C4 0.2898(3) 0.9363(3) 0.7441(2) 0.0228(5) Uani d . 1 . .
    H H4 0.1937 1.0201 0.7108 0.027 Uiso calc R 1 . .
    C C5 0.3153(3) 0.7571(4) 0.68168(19) 0.0214(4) Uani d . 1 . .
    H H5 0.2366 0.7193 0.6049 0.026 Uiso calc R 1 . .
    C C6 0.4554(3) 0.6303(3) 0.72981(19) 0.0175(4) Uani d . 1 . .
    C C7 0.4806(3) 0.4437(3) 0.6638(2) 0.0188(4) Uani d . 1 . .
    H H7 0.4019 0.4071 0.5868 0.023 Uiso calc R 1 . .
    C C8 0.6349(3) 0.1448(3) 0.64566(19) 0.0184(4) Uani d . 1 . .
    C C9 0.7588(3) -0.1475(3) 0.61665(18) 0.0178(4) Uani d . 1 . .
    C C10 0.8777(3) -0.3090(4) 0.6428(2) 0.0228(4) Uani d . 1 . .
    H H10 0.9681 -0.3056 0.7170 0.027 Uiso calc R 1 . .
    C C11 0.8612(3) -0.4729(4) 0.5589(2) 0.0249(5) Uani d . 1 . .
    H H11 0.9414 -0.5832 0.5757 0.030 Uiso calc R 1 . .
    C C12 0.7290(3) -0.4798(4) 0.4498(2) 0.0229(5) Uani d . 1 . .
    H H12 0.7212 -0.5939 0.3931 0.027 Uiso calc R 1 . .
    C C13 0.6081(3) -0.3219(4) 0.4225(2) 0.0213(4) Uani d . 1 . .
    H H13 0.5170 -0.3277 0.3488 0.026 Uiso calc R 1 . .
    C C14 0.6257(3) -0.1556(3) 0.5070(2) 0.0190(4) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0181(2) 0.0172(2) 0.0187(2) -0.0003(2) 0.00322(17) -0.00262(19)
    O1 0.0216(9) 0.0314(10) 0.0232(9) 0.0063(7) -0.0024(7) -0.0064(6)
    N1 0.0193(8) 0.0166(8) 0.0183(8) -0.0016(7) 0.0040(7) -0.0015(7)
    N2 0.0222(10) 0.0148(8) 0.0191(9) -0.0020(7) 0.0042(7) -0.0008(7)
    C1 0.0181(10) 0.0220(10) 0.0181(9) -0.0008(8) 0.0051(8) -0.0004(8)
    C2 0.0235(11) 0.0215(10) 0.0211(10) -0.0032(9) 0.0066(9) -0.0052(8)
    C3 0.0265(12) 0.0193(10) 0.0263(11) -0.0017(9) 0.0144(9) -0.0023(8)
    C4 0.0228(12) 0.0211(11) 0.0255(11) 0.0054(8) 0.0095(9) 0.0051(8)
    C5 0.0197(10) 0.0245(10) 0.0190(9) 0.0002(9) 0.0048(8) 0.0025(8)
    C6 0.0179(10) 0.0178(9) 0.0164(9) -0.0011(8) 0.0050(8) -0.0012(8)
    C7 0.0173(10) 0.0200(11) 0.0177(10) -0.0029(8) 0.0035(8) -0.0002(7)
    C8 0.0196(10) 0.0168(10) 0.0182(9) -0.0025(8) 0.0051(8) 0.0001(7)
    C9 0.0221(10) 0.0148(9) 0.0175(9) -0.0025(8) 0.0077(8) -0.0021(8)
    C10 0.0228(11) 0.0209(10) 0.0249(10) 0.0016(9) 0.0081(8) 0.0032(8)
    C11 0.0245(12) 0.0224(11) 0.0311(12) 0.0032(9) 0.0136(10) 0.0047(9)
    C12 0.0282(13) 0.0182(10) 0.0276(12) -0.0036(9) 0.0166(10) -0.0058(9)
    C13 0.0205(10) 0.0224(11) 0.0208(10) -0.0043(9) 0.0063(8) -0.0018(8)
    C14 0.0178(10) 0.0156(9) 0.0249(10) 0.0012(8) 0.0088(8) 0.0022(8)
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
    S1 C14 . 1.733(2) ?
    S1 C8 . 1.770(2) ?
    O1 C1 . 1.345(3) ?
    O1 H1 . 0.8672 ?
    N1 C7 . 1.294(3) ?
    N1 C8 . 1.389(3) ?
    N2 C8 . 1.286(3) ?
    N2 C9 . 1.394(3) ?
    C1 C2 . 1.393(3) ?
    C1 C6 . 1.410(3) ?
    C2 C3 . 1.383(4) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.394(4) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.381(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.400(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.442(3) ?
    C7 H7 . 0.9500 ?
    C9 C10 . 1.399(3) ?
    C9 C14 . 1.402(3) ?
    C10 C11 . 1.378(3) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.393(4) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.395(3) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.392(3) ?
    C13 H13 . 0.9500 ?
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
    C14 S1 C8 . . 88.21(11) ?
    C1 O1 H1 . . 102.4 ?
    C7 N1 C8 . . 121.20(18) ?
    C8 N2 C9 . . 109.65(18) ?
    O1 C1 C2 . . 118.56(19) ?
    O1 C1 C6 . . 121.8(2) ?
    C2 C1 C6 . . 119.7(2) ?
    C3 C2 C1 . . 120.4(2) ?
    C3 C2 H2 . . 119.8 ?
    C1 C2 H2 . . 119.8 ?
    C2 C3 C4 . . 120.3(2) ?
    C2 C3 H3 . . 119.8 ?
    C4 C3 H3 . . 119.8 ?
    C5 C4 C3 . . 119.7(2) ?
    C5 C4 H4 . . 120.2 ?
    C3 C4 H4 . . 120.2 ?
    C4 C5 C6 . . 121.0(2) ?
    C4 C5 H5 . . 119.5 ?
    C6 C5 H5 . . 119.5 ?
    C5 C6 C1 . . 118.87(19) ?
    C5 C6 C7 . . 120.47(19) ?
    C1 C6 C7 . . 120.7(2) ?
    N1 C7 C6 . . 120.7(2) ?
    N1 C7 H7 . . 119.7 ?
    C6 C7 H7 . . 119.7 ?
    N2 C8 N1 . . 119.83(19) ?
    N2 C8 S1 . . 116.81(16) ?
    N1 C8 S1 . . 123.36(17) ?
    N2 C9 C10 . . 124.3(2) ?
    N2 C9 C14 . . 115.84(19) ?
    C10 C9 C14 . . 119.9(2) ?
    C11 C10 C9 . . 118.8(2) ?
    C11 C10 H10 . . 120.6 ?
    C9 C10 H10 . . 120.6 ?
    C10 C11 C12 . . 121.1(2) ?
    C10 C11 H11 . . 119.4 ?
    C12 C11 H11 . . 119.4 ?
    C13 C12 C11 . . 121.1(2) ?
    C13 C12 H12 . . 119.5 ?
    C11 C12 H12 . . 119.5 ?
    C14 C13 C12 . . 117.7(2) ?
    C14 C13 H13 . . 121.2 ?
    C12 C13 H13 . . 121.2 ?
    C13 C14 C9 . . 121.5(2) ?
    C13 C14 S1 . . 129.07(18) ?
    C9 C14 S1 . . 109.47(16) ?
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
    O1 C1 C2 C3 . . . . -178.7(2) ?
    C6 C1 C2 C3 . . . . 1.4(3) ?
    C1 C2 C3 C4 . . . . 0.2(4) ?
    C2 C3 C4 C5 . . . . -1.2(4) ?
    C3 C4 C5 C6 . . . . 0.6(3) ?
    C4 C5 C6 C1 . . . . 0.9(3) ?
    C4 C5 C6 C7 . . . . -180.0(2) ?
    O1 C1 C6 C5 . . . . 178.2(2) ?
    C2 C1 C6 C5 . . . . -1.9(3) ?
    O1 C1 C6 C7 . . . . -0.9(3) ?
    C2 C1 C6 C7 . . . . 179.0(2) ?
    C8 N1 C7 C6 . . . . 179.8(2) ?
    C5 C6 C7 N1 . . . . -179.6(2) ?
    C1 C6 C7 N1 . . . . -0.5(3) ?
    C9 N2 C8 N1 . . . . 178.51(18) ?
    C9 N2 C8 S1 . . . . -1.1(2) ?
    C7 N1 C8 N2 . . . . -177.6(2) ?
    C7 N1 C8 S1 . . . . 2.0(3) ?
    C14 S1 C8 N2 . . . . 1.30(18) ?
    C14 S1 C8 N1 . . . . -178.28(18) ?
    C8 N2 C9 C10 . . . . -179.1(2) ?
    C8 N2 C9 C14 . . . . 0.2(3) ?
    N2 C9 C10 C11 . . . . 179.7(2) ?
    C14 C9 C10 C11 . . . . 0.4(3) ?
    C9 C10 C11 C12 . . . . -0.1(3) ?
    C10 C11 C12 C13 . . . . -0.6(4) ?
    C11 C12 C13 C14 . . . . 1.1(3) ?
    C12 C13 C14 C9 . . . . -0.8(3) ?
    C12 C13 C14 S1 . . . . 179.15(17) ?
    N2 C9 C14 C13 . . . . -179.33(19) ?
    C10 C9 C14 C13 . . . . 0.0(3) ?
    N2 C9 C14 S1 . . . . 0.7(2) ?
    C10 C9 C14 S1 . . . . -179.89(17) ?
    C8 S1 C14 C13 . . . . 179.0(2) ?
    C8 S1 C14 C9 . . . . -1.04(16) ?
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
    O1 H1 N1 . 0.87 1.73 2.550(2) 156 yes
