##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2011-09-14
_journal_date_accepted     2011-09-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue     10
_journal_page_first     o2700
_journal_page_last     o2700
_journal_paper_category     QO
_journal_coeditor_code     JH2331
_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
;\
4-(1,3-Benzothiazol-2-yl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-\
one
;
loop_
    _publ_author_name
    _publ_author_address
    'Chakib, Imane'
;
Laboratoire de Chimie Organique Hétérocyclique
Pôle de compétences Pharmacochimie
Université Mohammed V-Agdal
BP 1014 Avenue Ibn Batout
Rabat
Morocco
;
    'Zerzouf, Abdelfettah'
;
Laboratoire de Chimie Organique Hétérocyclique
Pôle de compétences Pharmacochimie
Université Mohammed V-Agdal
BP 1014 Avenue Ibn Batout
Rabat
Morocco
;
    'Rodi, Youssef Kandri'
;
Laboratoire de Chimie Organique Appliquée
Faculté des Sciences et Techniques
Université Sidi Mohamed Ben Abdallah
Fés
Morocco
;
    'Essassi, El Mokhtar'
;
Laboratoire de Chimie Organique Hétérocyclique
Pôle de compétences Pharmacochimie
Université Mohammed V-Agdal
BP 1014 Avenue Ibn Batout
Rabat
Morocco
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
and
Chemistry Department
Faculty of Science
King Abdulaziz University
PO Box 80203 Jeddah
Saudi Arabia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-(1,3-Benzothiazol-2-yl)-1,5-dimethyl-2-phenyl-1H-pyrazol-
3(2H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H15 N3 O S'
_chemical_formula_sum     'C18 H15 N3 O S'
_chemical_formula_iupac     'C18 H15 N3 O S'
_chemical_formula_weight     321.39
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     8.7428(2)
_cell_length_b     25.7551(5)
_cell_length_c     6.96600(10)
_cell_angle_alpha     90.00
_cell_angle_beta     97.4600(10)
_cell_angle_gamma     90.00
_cell_volume     1555.27(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3894
_cell_measurement_theta_min     2.50
_cell_measurement_theta_max     24.58
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.373
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     672
_exptl_absorpt_coefficient_mu     0.216
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.8997
_exptl_absorpt_correction_T_max     0.9787
_diffrn_ambient_temperature     293(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 APEXII'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     18953
_diffrn_reflns_av_R_equivalents     0.0532
_diffrn_reflns_av_sigmaI/netI     0.0418
_diffrn_reflns_theta_min     2.35
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_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     11
_diffrn_reflns_limit_k_min     -29
_diffrn_reflns_limit_k_max     33
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     9
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3569
_reflns_number_gt     2418
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0805
_refine_ls_R_factor_gt     0.0473
_refine_ls_wR_factor_gt     0.1135
_refine_ls_wR_factor_ref     0.1313
_refine_ls_goodness_of_fit_ref     1.013
_refine_ls_restrained_S_all     1.013
_refine_ls_number_reflns     3569
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0644P)²+0.2960P] 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     0.263
_refine_diff_density_min     -0.271
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.92125(7) 0.46686(2) 0.19736(8) 0.04602(18) Uani d . 1 1 . .
    N N1 0.8107(2) 0.43170(7) 0.5013(3) 0.0485(5) Uani d . 1 1 . .
    N N2 0.6696(2) 0.60559(6) 0.3813(2) 0.0450(4) Uani d . 1 1 . .
    N N3 0.6087(2) 0.58549(6) 0.5419(2) 0.0436(4) Uani d . 1 1 . .
    O O1 0.80712(19) 0.57089(6) 0.1499(2) 0.0555(4) Uani d . 1 1 . .
    C C1 0.9552(2) 0.40265(8) 0.2603(3) 0.0435(5) Uani d . 1 1 . .
    C C2 1.0365(3) 0.36554(8) 0.1694(3) 0.0531(6) Uani d . 1 1 . .
    H H2 1.0832 0.3740 0.0609 0.064 Uiso calc R 1 1 . .
    C C3 1.0459(3) 0.31630(9) 0.2442(4) 0.0611(7) Uani d . 1 1 . .
    H H3 1.1003 0.2910 0.1862 0.073 Uiso calc R 1 1 . .
    C C4 0.9756(3) 0.30371(9) 0.4045(4) 0.0682(7) Uani d . 1 1 . .
    H H4 0.9818 0.2698 0.4510 0.082 Uiso calc R 1 1 . .
    C C5 0.8967(3) 0.34025(9) 0.4969(4) 0.0657(7) Uani d . 1 1 . .
    H H5 0.8506 0.3313 0.6053 0.079 Uiso calc R 1 1 . .
    C C6 0.8869(2) 0.39090(8) 0.4253(3) 0.0462(5) Uani d . 1 1 . .
    C C7 0.8201(2) 0.47347(7) 0.3978(3) 0.0399(5) Uani d . 1 1 . .
    C C8 0.7531(2) 0.56620(8) 0.3030(3) 0.0417(5) Uani d . 1 1 . .
    C C9 0.7516(2) 0.52318(7) 0.4329(3) 0.0387(5) Uani d . 1 1 . .
    C C10 0.6676(2) 0.53751(7) 0.5781(3) 0.0398(5) Uani d . 1 1 . .
    C C11 0.6421(3) 0.50940(9) 0.7570(3) 0.0514(6) Uani d . 1 1 . .
    H H11A 0.5334 0.5064 0.7630 0.077 Uiso calc R 1 1 . .
    H H11B 0.6897 0.5282 0.8679 0.077 Uiso calc R 1 1 . .
    H H11C 0.6868 0.4754 0.7559 0.077 Uiso calc R 1 1 . .
    C C12 0.5534(3) 0.62109(9) 0.6788(3) 0.0527(6) Uani d . 1 1 . .
    H H12A 0.5437 0.6031 0.7972 0.079 Uiso calc R 1 1 . .
    H H12B 0.4546 0.6346 0.6253 0.079 Uiso calc R 1 1 . .
    H H12C 0.6252 0.6492 0.7045 0.079 Uiso calc R 1 1 . .
    C C13 0.5892(3) 0.64466(7) 0.2625(3) 0.0414(5) Uani d . 1 1 . .
    C C14 0.4314(3) 0.64253(9) 0.2115(3) 0.0532(6) Uani d . 1 1 . .
    H H14 0.3732 0.6167 0.2606 0.064 Uiso calc R 1 1 . .
    C C15 0.3615(3) 0.67960(10) 0.0859(4) 0.0657(7) Uani d . 1 1 . .
    H H15 0.2553 0.6787 0.0497 0.079 Uiso calc R 1 1 . .
    C C16 0.4484(4) 0.71801(10) 0.0139(4) 0.0673(8) Uani d . 1 1 . .
    H H16 0.4007 0.7428 -0.0705 0.081 Uiso calc R 1 1 . .
    C C17 0.6046(4) 0.71958(9) 0.0666(4) 0.0627(7) Uani d . 1 1 . .
    H H17 0.6629 0.7454 0.0175 0.075 Uiso calc R 1 1 . .
    C C18 0.6759(3) 0.68310(8) 0.1916(3) 0.0508(5) Uani d . 1 1 . .
    H H18 0.7820 0.6844 0.2281 0.061 Uiso calc R 1 1 . .
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 C1 . 1.727(2) ?
    S1 C7 . 1.755(2) ?
    N1 C7 . 1.304(2) ?
    N1 C6 . 1.386(3) ?
    N2 C8 . 1.401(3) ?
    N2 N3 . 1.399(2) ?
    N2 C13 . 1.428(2) ?
    N3 C10 . 1.350(2) ?
    N3 C12 . 1.451(3) ?
    O1 C8 . 1.227(2) ?
    C1 C2 . 1.392(3) ?
    C1 C6 . 1.395(3) ?
    C2 C3 . 1.369(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.382(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.375(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.395(3) ?
    C5 H5 . 0.9300 ?
    C7 C9 . 1.448(3) ?
    C8 C9 . 1.432(3) ?
    C9 C10 . 1.376(3) ?
    C10 C11 . 1.483(3) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C13 C18 . 1.377(3) ?
    C13 C14 . 1.381(3) ?
    C14 C15 . 1.382(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.381(4) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.368(4) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.374(3) ?
    C17 H17 . 0.9300 ?
    C18 H18 . 0.9300 ?
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
    C1 S1 C7 . . 88.78(10) ?
    C7 N1 C6 . . 110.27(18) ?
    C8 N2 N3 . . 108.35(15) ?
    C8 N2 C13 . . 121.79(16) ?
    N3 N2 C13 . . 120.94(17) ?
    C10 N3 N2 . . 108.24(16) ?
    C10 N3 C12 . . 127.40(17) ?
    N2 N3 C12 . . 119.07(16) ?
    C2 C1 C6 . . 121.6(2) ?
    C2 C1 S1 . . 128.56(18) ?
    C6 C1 S1 . . 109.83(16) ?
    C3 C2 C1 . . 118.1(2) ?
    C3 C2 H2 . . 120.9 ?
    C1 C2 H2 . . 120.9 ?
    C2 C3 C4 . . 120.9(2) ?
    C2 C3 H3 . . 119.5 ?
    C4 C3 H3 . . 119.5 ?
    C5 C4 C3 . . 121.4(2) ?
    C5 C4 H4 . . 119.3 ?
    C3 C4 H4 . . 119.3 ?
    C4 C5 C6 . . 119.0(2) ?
    C4 C5 H5 . . 120.5 ?
    C6 C5 H5 . . 120.5 ?
    N1 C6 C5 . . 125.6(2) ?
    N1 C6 C1 . . 115.37(18) ?
    C5 C6 C1 . . 119.0(2) ?
    N1 C7 C9 . . 125.38(19) ?
    N1 C7 S1 . . 115.75(15) ?
    C9 C7 S1 . . 118.85(15) ?
    O1 C8 N2 . . 123.08(18) ?
    O1 C8 C9 . . 131.43(19) ?
    N2 C8 C9 . . 105.45(17) ?
    C10 C9 C8 . . 107.86(17) ?
    C10 C9 C7 . . 129.34(18) ?
    C8 C9 C7 . . 122.65(19) ?
    N3 C10 C9 . . 109.58(17) ?
    N3 C10 C11 . . 120.60(19) ?
    C9 C10 C11 . . 129.77(19) ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N3 C12 H12A . . 109.5 ?
    N3 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    N3 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C18 C13 C14 . . 121.0(2) ?
    C18 C13 N2 . . 117.5(2) ?
    C14 C13 N2 . . 121.43(19) ?
    C15 C14 C13 . . 118.7(2) ?
    C15 C14 H14 . . 120.7 ?
    C13 C14 H14 . . 120.7 ?
    C14 C15 C16 . . 120.4(3) ?
    C14 C15 H15 . . 119.8 ?
    C16 C15 H15 . . 119.8 ?
    C17 C16 C15 . . 120.1(2) ?
    C17 C16 H16 . . 120.0 ?
    C15 C16 H16 . . 120.0 ?
    C16 C17 C18 . . 120.3(2) ?
    C16 C17 H17 . . 119.9 ?
    C18 C17 H17 . . 119.9 ?
    C17 C18 C13 . . 119.6(2) ?
    C17 C18 H18 . . 120.2 ?
    C13 C18 H18 . . 120.2 ?
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
    C8 N2 N3 C10 . . . . 7.4(2) ?
    C13 N2 N3 C10 . . . . 155.18(17) ?
    C8 N2 N3 C12 . . . . 163.59(18) ?
    C13 N2 N3 C12 . . . . -48.6(3) ?
    C7 S1 C1 C2 . . . . -179.4(2) ?
    C7 S1 C1 C6 . . . . 0.61(15) ?
    C6 C1 C2 C3 . . . . 1.2(3) ?
    S1 C1 C2 C3 . . . . -178.77(17) ?
    C1 C2 C3 C4 . . . . 0.4(4) ?
    C2 C3 C4 C5 . . . . -1.3(4) ?
    C3 C4 C5 C6 . . . . 0.5(4) ?
    C7 N1 C6 C5 . . . . -178.3(2) ?
    C7 N1 C6 C1 . . . . 0.0(3) ?
    C4 C5 C6 N1 . . . . 179.4(2) ?
    C4 C5 C6 C1 . . . . 1.1(4) ?
    C2 C1 C6 N1 . . . . 179.51(19) ?
    S1 C1 C6 N1 . . . . -0.5(2) ?
    C2 C1 C6 C5 . . . . -2.0(3) ?
    S1 C1 C6 C5 . . . . 177.98(18) ?
    C6 N1 C7 C9 . . . . 178.88(19) ?
    C6 N1 C7 S1 . . . . 0.5(2) ?
    C1 S1 C7 N1 . . . . -0.67(16) ?
    C1 S1 C7 C9 . . . . -179.16(17) ?
    N3 N2 C8 O1 . . . . 172.67(19) ?
    C13 N2 C8 O1 . . . . 25.2(3) ?
    N3 N2 C8 C9 . . . . -5.1(2) ?
    C13 N2 C8 C9 . . . . -152.51(18) ?
    O1 C8 C9 C10 . . . . -176.5(2) ?
    N2 C8 C9 C10 . . . . 1.0(2) ?
    O1 C8 C9 C7 . . . . -0.5(4) ?
    N2 C8 C9 C7 . . . . 176.98(18) ?
    N1 C7 C9 C10 . . . . 1.4(3) ?
    S1 C7 C9 C10 . . . . 179.71(16) ?
    N1 C7 C9 C8 . . . . -173.65(19) ?
    S1 C7 C9 C8 . . . . 4.7(3) ?
    N2 N3 C10 C9 . . . . -6.8(2) ?
    C12 N3 C10 C9 . . . . -160.4(2) ?
    N2 N3 C10 C11 . . . . 171.05(18) ?
    C12 N3 C10 C11 . . . . 17.4(3) ?
    C8 C9 C10 N3 . . . . 3.6(2) ?
    C7 C9 C10 N3 . . . . -172.02(19) ?
    C8 C9 C10 C11 . . . . -174.0(2) ?
    C7 C9 C10 C11 . . . . 10.4(4) ?
    C8 N2 C13 C18 . . . . -74.5(2) ?
    N3 N2 C13 C18 . . . . 142.02(19) ?
    C8 N2 C13 C14 . . . . 101.9(2) ?
    N3 N2 C13 C14 . . . . -41.5(3) ?
    C18 C13 C14 C15 . . . . 0.5(3) ?
    N2 C13 C14 C15 . . . . -175.8(2) ?
    C13 C14 C15 C16 . . . . -0.2(4) ?
    C14 C15 C16 C17 . . . . 0.0(4) ?
    C15 C16 C17 C18 . . . . -0.2(4) ?
    C16 C17 C18 C13 . . . . 0.5(3) ?
    C14 C13 C18 C17 . . . . -0.7(3) ?
    N2 C13 C18 C17 . . . . 175.78(19) ?
