##############################################################################
#                                                                            #
# 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_I
_audit_creation_method     'SHELXL-2019/3'
_chemical_name_systematic
;\
4-(Benzo[d]thiazol-2-yl)-1,2-dimethyl-1H-pyrazol-3(2H)-\
one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H11 N3 O S'
_chemical_formula_sum     'C12 H11 N3 O S'
_chemical_formula_iupac     'C12 H11 N3 O S'
_chemical_formula_weight     245.30
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     8.78308(12)
_cell_length_b     11.66215(16)
_cell_length_c     11.00169(15)
_cell_angle_alpha     90
_cell_angle_beta     97.9460(12)
_cell_angle_gamma     90
_cell_volume     1116.08(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     32695
_cell_measurement_theta_min     5.0830
_cell_measurement_theta_max     77.3970
_cell_measurement_temperature     100(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.460
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu     2.465
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_absorpt_correction_T_min     0.73075
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     100.0(3)
_diffrn_source     'micro-focus sealed X-ray tube'
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type     'XtaLAB Synergy'
_diffrn_measurement_method     'ω scans'
_diffrn_detector     'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean     10.0000
_diffrn_reflns_number     46018
_diffrn_reflns_av_R_equivalents     0.0372
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_theta_min     5.084
_diffrn_reflns_theta_max     77.640
_diffrn_reflns_theta_full     77.000
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     2367
_reflns_number_gt     2280
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0307
_refine_ls_R_factor_gt     0.0299
_refine_ls_wR_factor_gt     0.0807
_refine_ls_wR_factor_ref     0.0814
_refine_ls_goodness_of_fit_ref     1.068
_refine_ls_restrained_S_all     1.068
_refine_ls_number_reflns     2367
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0434P)²+0.4017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.284
_refine_diff_density_min     -0.360
_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' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.3331 0.5567
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)
;
_computing_cell_refinement
;
CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2019/3 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
XP, Version 5.03 (Bruker, 1998)
;
_computing_publication_material
;
SHELXL2019/3 (Sheldrick, 2015b)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.63680(4) 0.71933(2) 0.56971(3) 0.02849(11) Uani d 1 . .
    O O1 0.40109(11) 0.79924(7) 0.36636(8) 0.0311(2) Uani d 1 . .
    N N1 0.33946(12) 0.67380(9) 0.20375(9) 0.0266(2) Uani d 1 . .
    N N2 0.39212(12) 0.56914(8) 0.16939(9) 0.0268(2) Uani d 1 . .
    N N3 0.73240(12) 0.52608(9) 0.48701(10) 0.0288(2) Uani d 1 . .
    C C2 0.63324(14) 0.60863(10) 0.45966(11) 0.0259(2) Uani d 1 . .
    C C3A 0.82145(14) 0.54730(11) 0.59907(12) 0.0286(3) Uani d 1 . .
    C C4 0.94097(16) 0.47710(12) 0.65366(13) 0.0350(3) Uani d 1 . .
    H H4 0.964387 0.407342 0.615676 0.042 Uiso calc 1 . .
    C C5 1.02447(16) 0.51076(13) 0.76368(13) 0.0382(3) Uani d 1 . .
    H H5 1.106443 0.463964 0.800905 0.046 Uiso calc 1 . .
    C C6 0.98995(16) 0.61274(13) 0.82092(13) 0.0378(3) Uani d 1 . .
    H H6 1.049479 0.634461 0.896126 0.045 Uiso calc 1 . .
    C C7 0.87033(16) 0.68266(12) 0.76977(12) 0.0339(3) Uani d 1 . .
    H H7 0.845688 0.751223 0.809420 0.041 Uiso calc 1 . .
    C C7A 0.78751(14) 0.64905(11) 0.65836(11) 0.0284(3) Uani d 1 . .
    C C8 0.52570(14) 0.61387(10) 0.34907(11) 0.0258(2) Uani d 1 . .
    C C9 0.42066(14) 0.70641(10) 0.31446(11) 0.0258(2) Uani d 1 . .
    C C10 0.50225(14) 0.53273(10) 0.25637(11) 0.0267(3) Uani d 1 . .
    H H10 0.556198 0.462239 0.255040 0.032 Uiso calc 1 . .
    C C11 0.22779(15) 0.74119(11) 0.12468(12) 0.0313(3) Uani d 1 . .
    H H11A 0.260232 0.747813 0.043243 0.047 Uiso calc 1 . .
    H H11B 0.220412 0.817829 0.159925 0.047 Uiso calc 1 . .
    H H11C 0.127222 0.703488 0.117398 0.047 Uiso calc 1 . .
    C C12 0.32435(15) 0.51086(11) 0.05843(12) 0.0301(3) Uani d 1 . .
    H H12A 0.214516 0.498538 0.061218 0.045 Uiso calc 1 . .
    H H12B 0.375258 0.436717 0.052279 0.045 Uiso calc 1 . .
    H H12C 0.337515 0.557948 -0.013158 0.045 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C7A . 1.7374(13) y
    S1 C2 . 1.7673(12) y
    O1 C9 . 1.2468(15) y
    N1 N2 . 1.3766(14) y
    N1 C9 . 1.3772(16) y
    N1 C11 . 1.4493(16) ?
    N2 C10 . 1.3326(16) y
    N2 C12 . 1.4511(15) ?
    N3 C2 . 1.3051(16) y
    N3 C3A . 1.3879(16) y
    C2 C8 . 1.4348(17) y
    C3A C4 . 1.3995(18) ?
    C3A C7A . 1.4058(18) y
    C4 C5 . 1.383(2) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.398(2) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.386(2) ?
    C6 H6 . 0.9500 ?
    C7 C7A . 1.3923(18) ?
    C7 H7 . 0.9500 ?
    C8 C10 . 1.3856(17) ?
    C8 C9 . 1.4365(17) ?
    C10 H10 . 0.9500 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
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
    C7A S1 C2 . . 88.85(6) y
    N2 N1 C9 . . 109.59(10) y
    N2 N1 C11 . . 122.76(10) ?
    C9 N1 C11 . . 127.29(10) ?
    C10 N2 N1 . . 108.87(10) y
    C10 N2 C12 . . 128.87(10) ?
    N1 N2 C12 . . 122.15(10) ?
    C2 N3 C3A . . 110.45(11) y
    N3 C2 C8 . . 124.55(11) y
    N3 C2 S1 . . 115.65(9) y
    C8 C2 S1 . . 119.80(9) y
    N3 C3A C4 . . 125.04(12) y
    N3 C3A C7A . . 115.66(11) y
    C4 C3A C7A . . 119.29(12) ?
    C5 C4 C3A . . 119.03(13) ?
    C5 C4 H4 . . 120.5 ?
    C3A C4 H4 . . 120.5 ?
    C4 C5 C6 . . 120.93(13) ?
    C4 C5 H5 . . 119.5 ?
    C6 C5 H5 . . 119.5 ?
    C7 C6 C5 . . 121.11(13) ?
    C7 C6 H6 . . 119.4 ?
    C5 C6 H6 . . 119.4 ?
    C6 C7 C7A . . 117.78(13) ?
    C6 C7 H7 . . 121.1 ?
    C7A C7 H7 . . 121.1 ?
    C7 C7A C3A . . 121.85(12) ?
    C7 C7A S1 . . 128.77(11) y
    C3A C7A S1 . . 109.37(9) y
    C10 C8 C2 . . 127.48(11) y
    C10 C8 C9 . . 107.06(11) y
    C2 C8 C9 . . 125.46(11) y
    O1 C9 N1 . . 123.88(11) y
    O1 C9 C8 . . 130.92(12) y
    N1 C9 C8 . . 105.19(10) y
    N2 C10 C8 . . 109.28(11) y
    N2 C10 H10 . . 125.4 ?
    C8 C10 H10 . . 125.4 ?
    N1 C11 H11A . . 109.5 ?
    N1 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    N1 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N2 C12 H12A . . 109.5 ?
    N2 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    N2 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
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
    C9 N1 N2 C10 . . . . 1.41(13) ?
    C11 N1 N2 C10 . . . . 174.94(11) ?
    C9 N1 N2 C12 . . . . 177.72(11) ?
    C11 N1 N2 C12 . . . . -8.75(17) ?
    C3A N3 C2 C8 . . . . 178.92(11) ?
    C3A N3 C2 S1 . . . . -1.06(13) ?
    C7A S1 C2 N3 . . . . 1.17(10) ?
    C7A S1 C2 C8 . . . . -178.81(10) ?
    C2 N3 C3A C4 . . . . -178.36(12) ?
    C2 N3 C3A C7A . . . . 0.34(15) ?
    N3 C3A C4 C5 . . . . 177.54(13) ?
    C7A C3A C4 C5 . . . . -1.12(19) ?
    C3A C4 C5 C6 . . . . 0.6(2) ?
    C4 C5 C6 C7 . . . . 0.5(2) ?
    C5 C6 C7 C7A . . . . -1.2(2) ?
    C6 C7 C7A C3A . . . . 0.65(19) ?
    C6 C7 C7A S1 . . . . -177.91(10) ?
    N3 C3A C7A C7 . . . . -178.29(11) ?
    C4 C3A C7A C7 . . . . 0.49(19) ?
    N3 C3A C7A S1 . . . . 0.52(14) ?
    C4 C3A C7A S1 . . . . 179.30(10) ?
    C2 S1 C7A C7 . . . . 177.82(13) ?
    C2 S1 C7A C3A . . . . -0.88(9) ?
    N3 C2 C8 C10 . . . . 3.3(2) ?
    S1 C2 C8 C10 . . . . -176.73(10) ?
    N3 C2 C8 C9 . . . . -176.88(11) ?
    S1 C2 C8 C9 . . . . 3.10(17) ?
    N2 N1 C9 O1 . . . . 177.75(11) ?
    C11 N1 C9 O1 . . . . 4.6(2) ?
    N2 N1 C9 C8 . . . . -1.34(13) ?
    C11 N1 C9 C8 . . . . -174.50(11) ?
    C10 C8 C9 O1 . . . . -178.19(13) ?
    C2 C8 C9 O1 . . . . 1.9(2) ?
    C10 C8 C9 N1 . . . . 0.80(13) ?
    C2 C8 C9 N1 . . . . -179.06(11) ?
    N1 N2 C10 C8 . . . . -0.86(13) ?
    C12 N2 C10 C8 . . . . -176.86(12) ?
    C2 C8 C10 N2 . . . . 179.88(12) ?
    C9 C8 C10 N2 . . . . 0.03(14) ?
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
    C10 H10 O1 2_645 0.95 2.38 3.2055(15) 144.7 yes
    C11 H11A O1 4_575 0.98 2.51 3.4368(16) 158.4 yes
    C12 H12B S1 2_645 0.98 2.86 3.7142(13) 145.7 yes
    C12 H12B O1 2_645 0.98 2.60 3.4696(16) 148.4 yes
    C12 H12C O1 4_575 0.98 2.25 3.1966(16) 163.0 yes
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.709
_shelx_estimated_absorpt_T_max     0.930
data_global
_journal_date_recd_electronic     2024-01-22
_journal_date_accepted     2024-02-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2024
_journal_volume     80
_journal_issue      3
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989024001257
_journal_coeditor_code     YZ2050
_publ_contact_author_name
;
Peter G. Jones
;
_publ_contact_author_address
;
Institut für Anorganische und Analytische Chemie
     Technische Universität Braunschweig
     Hagenring 30
     D-38106 Braunschweig
     Germany
;
_publ_contact_author_email     'p.jones@tu-braunschweig.de'
_publ_contact_author_fax      495313915387
_publ_contact_author_phone      495313915382
_publ_section_title
;\
Crystal structure of
4-(benzo[d]thiazol-2-yl)-1,2-dimethyl-1H-pyrazol-3(2H)-\
one
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_address
    'Elboshi, Heba A.'
;
Chemistry Department
Faculty of Science
Helwan University
Cairo
Egypt
;
    'Azzam, Rasha A.'
;
Chemistry Department
Faculty of Science
Helwan University
Cairo
Egypt
;
    'Elgemeie, Galal H.'
;
Chemistry Department
Faculty of Science
Helwan University
Cairo
Egypt
;
    'Jones, Peter G.'
;
Institut für Anorganische und Analytische Chemie
Technische Universität Braunschweig
Hagenring 30
D-38106 Braunschweig
Germany
;
_publ_section_synopsis
;\
The ring systems of
4-(benzo[d]thiazol-2-yl)-1,2-dimethyl-1H-pyrazol-3(2H)-\
one are almost coplanar. In the three-dimensional packing, the carbonyl
oxygen accepts four weak hydrogen bonds.
;
