#------------------------------------------------------------------------------
#$Date: 2017-07-25 12:25:24 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199114 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/21/2242137.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_2242137
loop_
_publ_author_name
'Azzam, Rasha A.'
'Elgemeie, Galal H.'
'Elsayed, Rasha E.'
'Jones, Peter G.'
_publ_section_title
;
 Crystal structure of
 N'-[2-(benzo[d]thiazol-2-yl)acetyl]-4-methylbenzenesulfonohydrazide
;
_journal_coeditor_code           HG5489
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1041
_journal_page_last               1043
_journal_paper_doi               10.1107/S2056989017008738
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C16 H15 N3 O3 S2'
_chemical_formula_moiety         'C16 H15 N3 O3 S2'
_chemical_formula_sum            'C16 H15 N3 O3 S2'
_chemical_formula_weight         361.43
_chemical_name_systematic
N'-[2-(Benzo[d]thiazol-2-yl)acetyl]-4-methylbenzenesulfonohydrazide
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.905(4)
_cell_angle_beta                 98.142(4)
_cell_angle_gamma                101.576(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3436(4)
_cell_length_b                   9.7591(5)
_cell_length_c                   10.8815(6)
_cell_measurement_reflns_used    13640
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7750
_cell_measurement_theta_min      2.6290
_cell_volume                     846.59(8)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            45592
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         31.05
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku Oxford Diffraction, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.417
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5040
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0354P)²+0.3550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                4503
_reflns_number_total             5040
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            hg5489sup1.cif
_cod_data_source_block           I
_cod_database_code               2242137
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S S1 0.57619(4) 0.26397(3) 0.86910(3) 0.01947(7) Uani d . 1 1
C C2 0.56817(13) 0.15226(11) 0.72845(10) 0.01492(19) Uani d . 1 1
N N3 0.46391(11) 0.03031(9) 0.70990(9) 0.01448(17) Uani d . 1 1
C C3A 0.38014(13) 0.01774(11) 0.81106(10) 0.01466(19) Uani d . 1 1
C C4 0.25456(14) -0.09823(12) 0.81811(11) 0.0185(2) Uani d . 1 1
H H4 0.2221 -0.1782 0.7522 0.022 Uiso calc R 1 1
C C5 0.17867(14) -0.09401(13) 0.92308(12) 0.0223(2) Uani d . 1 1
H H5 0.0920 -0.1714 0.9287 0.027 Uiso calc R 1 1
C C6 0.22767(15) 0.02293(14) 1.02157(11) 0.0238(2) Uani d . 1 1
H H6 0.1749 0.0225 1.0934 0.029 Uiso calc R 1 1
C C7 0.35125(15) 0.13868(13) 1.01602(11) 0.0223(2) Uani d . 1 1
H H7 0.3840 0.2178 1.0827 0.027 Uiso calc R 1 1
C C7A 0.42644(13) 0.13542(12) 0.90892(10) 0.0170(2) Uani d . 1 1
C C8 0.66708(13) 0.20010(12) 0.63115(11) 0.0172(2) Uani d . 1 1
H H8A 0.6814 0.1169 0.5740 0.021 Uiso calc R 1 1
H H8B 0.7784 0.2573 0.6723 0.021 Uiso calc R 1 1
C C9 0.57197(12) 0.28914(11) 0.55711(10) 0.01401(19) Uani d . 1 1
N N1 0.50433(11) 0.22734(9) 0.43761(9) 0.01544(17) Uani d . 1 1
H H01 0.519(2) 0.1475(18) 0.4007(15) 0.027(4) Uiso d . 1 1
N N2 0.40574(11) 0.29335(10) 0.35950(9) 0.01529(17) Uani d . 1 1
H H02 0.434(2) 0.3829(18) 0.3759(15) 0.029(4) Uiso d . 1 1
O O1 0.12667(11) 0.31786(9) 0.27597(8) 0.02335(18) Uani d . 1 1
S S2 0.20281(3) 0.23646(3) 0.35718(2) 0.01622(7) Uani d . 1 1
O O2 0.16863(11) 0.08446(8) 0.32664(8) 0.02168(17) Uani d . 1 1
O O3 0.55748(10) 0.40588(8) 0.60522(8) 0.01870(16) Uani d . 1 1
C C11 0.16430(13) 0.28095(11) 0.51069(11) 0.0163(2) Uani d . 1 1
C C12 0.15942(14) 0.42100(12) 0.55429(12) 0.0203(2) Uani d . 1 1
H H12 0.1721 0.4901 0.5007 0.024 Uiso calc R 1 1
C C13 0.13587(15) 0.45785(12) 0.67661(12) 0.0233(2) Uani d . 1 1
H H13 0.1329 0.5532 0.7069 0.028 Uiso calc R 1 1
C C14 0.11639(14) 0.35757(13) 0.75641(11) 0.0208(2) Uani d . 1 1
C C15 0.11840(13) 0.21746(12) 0.71012(11) 0.0196(2) Uani d . 1 1
H H15 0.1023 0.1477 0.7628 0.023 Uiso calc R 1 1
C C16 0.14367(13) 0.17876(11) 0.58797(11) 0.0176(2) Uani d . 1 1
H H16 0.1468 0.0835 0.5575 0.021 Uiso calc R 1 1
C C17 0.09014(19) 0.39948(16) 0.88922(13) 0.0327(3) Uani d . 1 1
H H17A 0.0428 0.4838 0.8946 0.049 Uiso calc PR 0.50 1
H H17B 0.1969 0.4207 0.9468 0.049 Uiso calc PR 0.50 1
H H17C 0.0137 0.3212 0.9127 0.049 Uiso calc PR 0.50 1
H H17D 0.1261 0.3334 0.9415 0.049 Uiso calc PR 0.50 1
H H17E -0.0280 0.3964 0.8893 0.049 Uiso calc PR 0.50 1
H H17F 0.1552 0.4960 0.9233 0.049 Uiso calc PR 0.50 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
C7A S1 C2 89.39(5) y
N3 C2 C8 122.61(10) ?
N3 C2 S1 115.98(8) ?
C8 C2 S1 121.25(8) ?
C2 N3 C3A 110.63(9) ?
N3 C3A C4 124.96(10) ?
N3 C3A C7A 114.86(10) ?
C4 C3A C7A 120.15(10) ?
C5 C4 C3A 118.54(11) ?
C4 C5 C6 120.98(11) ?
C7 C6 C5 121.26(11) ?
C6 C7 C7A 117.79(11) ?
C7 C7A C3A 121.26(11) ?
C7 C7A S1 129.57(9) ?
C3A C7A S1 109.14(8) ?
C2 C8 C9 107.51(8) ?
O3 C9 N1 123.90(10) ?
O3 C9 C8 121.56(10) ?
N1 C9 C8 114.53(9) ?
C9 N1 N2 121.14(9) y
N1 N2 S2 112.94(7) y
O1 S2 O2 120.92(5) ?
O1 S2 N2 103.98(5) ?
O2 S2 N2 106.20(5) ?
O1 S2 C11 109.49(5) ?
O2 S2 C11 107.66(5) ?
N2 S2 C11 107.89(5) ?
C16 C11 C12 120.86(10) ?
C16 C11 S2 120.35(8) ?
C12 C11 S2 118.76(9) ?
C13 C12 C11 119.02(11) ?
C12 C13 C14 121.22(10) ?
C15 C14 C13 118.82(11) ?
C15 C14 C17 120.67(12) ?
C13 C14 C17 120.50(11) ?
C16 C15 C14 120.77(11) ?
C15 C16 C11 119.28(10) ?
C5 C4 H4 120.7 ?
C3A C4 H4 120.7 ?
C4 C5 H5 119.5 ?
C6 C5 H5 119.5 ?
C7 C6 H6 119.4 ?
C5 C6 H6 119.4 ?
C6 C7 H7 121.1 ?
C7A C7 H7 121.1 ?
C2 C8 H8A 110.2 ?
C9 C8 H8A 110.2 ?
C2 C8 H8B 110.2 ?
C9 C8 H8B 110.2 ?
H8A C8 H8B 108.5 ?
C9 N1 H01 124.9(11) ?
N2 N1 H01 113.9(11) ?
N1 N2 H02 113.1(11) ?
S2 N2 H02 111.0(11) ?
C13 C12 H12 120.5 ?
C11 C12 H12 120.5 ?
C12 C13 H13 119.4 ?
C14 C13 H13 119.4 ?
C16 C15 H15 119.6 ?
C14 C15 H15 119.6 ?
C15 C16 H16 120.4 ?
C11 C16 H16 120.4 ?
C14 C17 H17A 109.5 ?
C14 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C14 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C14 C17 H17D 109.5 ?
H17A C17 H17D 141.1 ?
H17B C17 H17D 56.3 ?
H17C C17 H17D 56.3 ?
C14 C17 H17E 109.5 ?
H17A C17 H17E 56.3 ?
H17B C17 H17E 141.1 ?
H17C C17 H17E 56.3 ?
H17D C17 H17E 109.5 ?
C14 C17 H17F 109.5 ?
H17A C17 H17F 56.3 ?
H17B C17 H17F 56.3 ?
H17C C17 H17F 141.1 ?
H17D C17 H17F 109.5 ?
H17E C17 H17F 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7A 1.7310(12) ?
S1 C2 1.7373(11) y
C2 N3 1.2972(14) y
C2 C8 1.4996(15) ?
N3 C3A 1.3914(14) ?
C3A C4 1.3983(15) ?
C3A C7A 1.4040(15) ?
C4 C5 1.3819(16) ?
C5 C6 1.4037(18) ?
C6 C7 1.3826(18) ?
C7 C7A 1.3992(16) ?
C8 C9 1.5238(14) ?
C9 O3 1.2231(13) ?
C9 N1 1.3464(14) ?
N1 N2 1.4069(12) y
N2 S2 1.6680(10) ?
O1 S2 1.4325(8) ?
S2 O2 1.4353(8) ?
S2 C11 1.7580(11) ?
C11 C16 1.3907(16) ?
C11 C12 1.3944(15) ?
C12 C13 1.3821(17) ?
C13 C14 1.3957(18) ?
C14 C15 1.3949(16) ?
C14 C17 1.5056(17) ?
C15 C16 1.3882(16) ?
C4 H4 0.9500 ?
C5 H5 0.9500 ?
C6 H6 0.9500 ?
C7 H7 0.9500 ?
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
N1 H01 0.866(16) ?
N2 H02 0.845(17) ?
C12 H12 0.9500 ?
C13 H13 0.9500 ?
C15 H15 0.9500 ?
C16 H16 0.9500 ?
C17 H17A 0.9800 ?
C17 H17B 0.9800 ?
C17 H17C 0.9800 ?
C17 H17D 0.9800 ?
C17 H17E 0.9800 ?
C17 H17F 0.9800 ?
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
N1 H01 N3 2_656 0.866(16) 2.013(16) 2.8717(13) 171.0(15)
N2 H02 O3 2_666 0.845(17) 2.029(17) 2.8553(12) 165.7(16)
C6 H6 O2 1_556 0.95 2.54 3.4142(15) 153.6
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
C7A S1 C2 N3 0.45(8) ?
C7A S1 C2 C8 175.95(9) ?
C8 C2 N3 C3A -175.40(9) ?
S1 C2 N3 C3A 0.03(11) ?
C2 N3 C3A C4 177.18(10) ?
C2 N3 C3A C7A -0.66(13) ?
N3 C3A C4 C5 -177.98(10) ?
C7A C3A C4 C5 -0.24(16) ?
C3A C4 C5 C6 -0.91(17) ?
C4 C5 C6 C7 1.12(18) ?
C5 C6 C7 C7A -0.15(17) ?
C6 C7 C7A C3A -1.00(16) ?
C6 C7 C7A S1 176.79(9) ?
N3 C3A C7A C7 179.17(10) ?
C4 C3A C7A C7 1.22(16) ?
N3 C3A C7A S1 0.98(11) ?
C4 C3A C7A S1 -176.98(8) ?
C2 S1 C7A C7 -178.77(11) ?
C2 S1 C7A C3A -0.76(8) ?
N3 C2 C8 C9 94.63(11) ?
S1 C2 C8 C9 -80.57(10) y
C2 C8 C9 O3 68.95(13) ?
C2 C8 C9 N1 -109.79(10) y
O3 C9 N1 N2 -1.96(16) ?
C8 C9 N1 N2 176.74(9) y
C9 N1 N2 S2 -96.08(10) y
N1 N2 S2 O1 178.74(7) ?
N1 N2 S2 O2 -52.67(8) ?
N1 N2 S2 C11 62.53(8) y
O1 S2 C11 C16 146.33(9) ?
O2 S2 C11 C16 13.11(10) ?
N2 S2 C11 C16 -101.12(9) ?
O1 S2 C11 C12 -35.40(10) ?
O2 S2 C11 C12 -168.61(9) ?
N2 S2 C11 C12 77.16(9) y
C16 C11 C12 C13 0.85(17) ?
S2 C11 C12 C13 -177.42(9) ?
C11 C12 C13 C14 -0.25(18) ?
C12 C13 C14 C15 -1.00(18) ?
C12 C13 C14 C17 -179.74(12) ?
C13 C14 C15 C16 1.68(17) ?
C17 C14 C15 C16 -179.58(11) ?
C14 C15 C16 C11 -1.10(16) ?
C12 C11 C16 C15 -0.18(16) ?
S2 C11 C16 C15 178.06(8) ?
H01 N1 N2 H02 -146.7(17) y
O3 C9 N1 H01 175.5(13) y
H02 N2 S2 O2 179.1(12) y

_cod_database_fobs_code 2242137
